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How To Play A Rogue Assassin

So you’re thinking about playing a Rogue Assassin in 5th Edition Dungeons & Dragons? It is certainly one of the most iconic archetypes in the game and one that allows you to do deadly damage to your foes, and in the right circumstances, much more damage with one blow than fighters and wizards can hope to do. Which, together with their penchant for stealth and deception, makes them a pretty exciting prospect to play.

In this post we’ll take a look at how we can build really fun Assassin characters to play (or rather Rogue characters with a view to selecting the Assassin archetype at 3rd Level), along with what skills and proficiencies are going to make you the most effective when it comes to the mechanics of the game (ie. combat and sneaking around like a mofo).

I’m a priest, honest! (Image by Pcwallart.com).

Let’s look first at the roleplaying aspect, because hey, this is a roleplaying game after all, and whilst rolling dice is fun, the RPG pay off usually comes when we successfully breath life into our stats sheet…

The Character Side of Your Character


The first question that you have to ask yourself when creating an Assassin is how did they get into the killing game? Are you a cold-hearted bastard who considers that if everyone has to die at some point, why not make a profit from it? Or are you a principled killer: a vigilante who only deals death to those that have it coming to them (in your humble opinion)? Are you a religious killer… dedicated to the fatal work of your deity? Maybe you were trained since childhood by an Assassin’s Guild to be an agent of death – killing has become an instinct to you, perfected by your perverse upbringing. Consider as well that your character doesn’t have to be a 24 carat pure Assassin. Maybe they are a spy or secret agent, who just happens to be particularly good at drawing a dagger across the throats of those who stand in their way – more in the mould of a medieval James Bond.

Once you’ve answered that question you also need to consider how then you ended up with your fellow player characters, as an adventurer. Have you reformed your ways (for those starting at 1st Level this could be a bit problematic as you don’t technically become an Assassin until 3rd Level)? Are you between contracts and in need of some fast cash (if so, why… do you owe someone important a big debt?)? Has an NPC sent you to spy on your fellow players? Have you been sent adventuring by your guild to get some real world experience? Or maybe you’ve rejected and run away from your guild training (let’s hope they took it well!)?

In all cases you should consult with your DM… if you’re spying on your fellow players for example do you need to present yourself as something else and hide your Rogue abilities? Or in the example where you were raised as a child by your guild, do you at first represent the guild loyally (until at least 3rd level when you complete your training) before starting to have doubts about the life you were groomed into? This could be a great story development which you could play out. By communicating with your DM you will both get ideas from him about how you can fit into his world and his adventure, as well as fit into the party, and in turn – if he’s a good DM – give him plot hooks that can shape the story you will be building together.

When I built my own Rogue Assassin I decided to create a full profile of the White Scorpions Assassin’s Guild to give more colour to my hitwoman, complete with guild history, power structure, current grandmaster, favoured killing methods, initiation ceremony and motto. I will share it soon with you!

Using Official D&D “Backgrounds”

Don’t forget to take advantage of the excellent Backgrounds section in the 5th Edition Player’s Handbook to flesh our your character (or even create them from scratch). Charlatan, Criminal and Urchin are the obvious ones to consider, but often the best character ideas come from combining two seemingly miss-matched premises. What if the bespectacled and weedy cartographer (Guild Artisan background) puts down his pen and inks at night to fire poisoned darts into his victims’ necks from his hand-made blowgun? Or maybe the boyish Orlando Bloom lookalike uses his celebrity status as playboy poet (Entertainer background) to infiltrate the palaces and castles of the rich and famous in order to do his dirty work.

Once you’ve made a decision be sure to roll on the Personality Trait, Ideal, Bond and Flaw tables. As you get a sense of your character you might prefer to choose one (or more) from each table (or from the tables of another background) than roll randomly… then again rolling randomly can do wonders for your creativity, as it forces you to join the dots in a credible way, no matter how far away they are.

Rolling randomly on the Charlatan’s tables just now I got the following:

Personality Trait
3. Flattery is my preferred trick for getting what I want.

2. Fairness. I never target people who can’t afford to lose a few coins.

6. I swindled and ruined a person who didn’t deserve it. I seek to atone for my misdeeds but might never be able to forgive myself.

2. I’m always in debt. I spend my ill gotten gains on decadent luxuries faster than I bring them in.

From these rolls I’m already getting a firm idea of a new character. A lush gambler with a love of the high life, who once – out of desperation – conned a woman who loved him out of her life fortune. She died shortly after and he has never quite forgiven himself, but nor has he managed to clean up his act completely. He still robs, cheats and cons to pay for his lifestyle, but only from the rich. He is sounding more like a Thief than an Assassin, but I’m going to toughen him up a bit by imagining he is from low nobility and an experienced dueller with the rapier. His goal in any fight is simply to win by any means necessary, preferably without exposing himself to any danger, explaining his ability to use the Rogue’s Sneak Attack ability and later Assassinate ability. In short he is a dissolute rake, with a thin sense of honour, but a sense of honour nonetheless and it could be a lot of fun playing with the ambiguities in his character.

So there you go guys… roll dem dice and watch as – out of thin air – a fully fledged character idea emerges!

Important: Fitting Into The Party

Remember, whilst you might have a lot of fun spying on your fellow characters, lying to them and creating chaos, it’s not always that much fun for the others – especially if you end up stabbing them in the back with a poisoned dagger “because it’s in my character”. One of the challenges of playing Assassins, and Rogues in general, is finding a credible reason for them to be with the party and not only that but be on their side, and keep the game fun for everyone. Even if you start by spying on them, perhaps later, after they’ve saved your life more times that you can count, your loyalties and values change and you become a trusted team member.

I solved this problem by having my Assassin work for a guild who deal in strictly just killings. This meant I could play a principled character of chaotic good alignment, one who could ally easily with the objectives of my party as they performed various missions against the forces of evil.

Lovely night for a lakeside stroll isn’t it?

Building A Kick-Ass Assassin

Now that you’ve got a solid backstory, let’s engage in a bit of powergaming (I know you didn’t really come here for the roleplaying tips!) and take a look at how to build your character for maximum effectiveness.

Choosing Your Race

Dexterity is what all Rogues live and die by, so it makes sense to look at the races that start by giving you a boost on this crucial skill. That is Elf (+2), Forest Gnome (+1), Halfling (+2) and Human (+1), and potentially Half Elf (+1). The idea of a Forest Gnome or Halfling Assassin seems fairly ludicrous to me… but then again remember what I said before about mismatches leading to great characters! What about a happy go lucky, somewhat portly female halfling, a maternal figure who loves singing, cooking, cleaning… and killing people? However, if you’ve been inspired by visions of a stealthy ninja-like shadow slinking over castle parapets and firing poisoned crossbow bolts at corrupt Princes then definitely Elf, Human or Half Elf make more sense. If you consider that humans can’t see in the dark, which is a major disadvantage if you’re Assassin, I’d put Elf and Half Elf ahead. As I find the idea of an Elf Assassin incongruous with their nature (and a Dark Elf one too cliched), I’d put Half Elf as my favourite Assassin race. (Half Orcs and Tieflings as natural outsiders could be decent shouts too).

Whatever you decide bump Dex up to the maximum, as you’ll be using it for the majority of your skills, your AC, initiative and your to hit and damage modifiers. Second tier attributes are Charisma (so that you can have a lot of fun conning, charming and deceiving NPCs) and Intelligence (for Investigation, but more importantly for when you multiclass as a Wizard, as I’m going to suggest!), whilst Constitution is handy if you plan to fight hand to hand in combat (more fun than pussying around with bows IMHO!), especially as you are only proficient in light armour and therefore relatively easy to hit. Strength is useless to you, especially if your DM lets you use Acrobatics for climbing checks (as our does!), and Wisdom too, as you’ll take Expertise function in Perception the only skill for which you will need it (although you will fail an annoying amount of Saving Throws because of it!).

Choosing Proficiencies

The Rogue class gives you four proficiencies, you should get an extra two from your background, plus Half Elf as a Race grants you another two, so you could start the game with a whopping 8 proficiencies – two of which you can choose Expertise in, allowing you to double your proficiency bonus. Here are the most useful ones, starting with what I consider the most essential.

Stealth – Hiding and sneaking up on foes is key to taking advantage of your Sneak Attack and Assassinate skills. Choose expertise in this.
Perception – Probably the most rolled skill check in the game, plus no one likes being surprised. Consider strongly for expertise.
Acrobatics – Depending on your DM you might roll Acrobatics for jumping over rooftops, tumbling out of windows and cartwheeling out of danger, or sometimes Athletics. I love Acrobatics but possibly if you have a high Dex. anyway and your DM insists on Athletics checks for climbing and jumping choose Athletics instead.
Athletics – See above.
Sleight of Hand – Useful for slipping poison into your victim’s wine and other subtleties.
Deception – Fast talking, lying, charming or disguising yourself.
Insight – For determining if others are lying to you.
Investigation – Useful for finding traps and hidden objects, although many DMs use Perception checks.
Persuasion – For general charm.
Arcana – Useful if you want to multiclass as a Wizard later.

Optimising Combat

One weapon combination really stands out for Assassin’s as the best and that is fighting with two short swords (or for a more oriental flavour scimitars), one in each hand. The rules state (p.195 of the Player’s Handbook) that as long as both weapons are “light” then you can use your main action to attack with one, and your bonus action to attack with the other. As shortswords (and scimitars) are not only “light” but also “finesse” weapons you can use your Dexterity modifier for both attack and damage rolls (note, when you use your bonus action to attack with your offhand you don’t get a damage bonus however). This means you can not only use your best skill modifier in combat but you get more attacks than most fighters at first level. There’s an additional reason for favouring two weapons however. As a Rogue you will want to be initiating combat more often than not, jumping out of shadows to get your Sneak Attack / Assassinate bonuses. Once you’ve been spotted however getting your Sneak Attack bonus is harder… you may have to dissolve into the melee to reappear somewhere else, or flank a creature already engaged in the fight… which means you really don’t want to miss your initial thrust, or any other time you get a Sneak Attack. With two chances to hit that means even if you mess up your first attack, you can still strike using your bonus action and ensure your Sneak Attack damage gets dealt (you can only do Sneak Attack damage once a turn).

Aside from two shortswords / scimitars (or daggers if you fancy a weapon you can throw as well!), you will want to carry a range weapon. Range weapons still qualify for Sneak Attack and since you’re likely not to the toughest or heavily armoured dude on the battlefield being able to keep your distance on occasion is invaluable. Unless you’re a shortass (halfling or gnome) then a longbow beats a shortbow, and whilst a crossbow is stylish if I was the DM I would find ways to penalise anyone trying to sneak around with an 18lb heavy crossbow, so a light or handcrossbow makes more sense.

Finally, whilst you might put yourself at a disadvantage in terms of game mechanics, an iconic weapon can lend a lot of fun flavour to your character. For this reason you might want to consider fighting with a scimitar and sickle, blowgun, or perhaps poison-coated whip. Check out this list for inspiration. Seriously regretting not arming my own character with a Xena Warrior Princess style Chakram. Speak to your DM about making fair rules for any new weapons.

Using Poison

Poison somewhat problematic in D&D as really there’s little reason why an Assassin wouldn’t be using deadly poison nonstop… other than the fact it would unbalance the game. I guess for that reason using poisons is expensive and a little impractical. In the Player’s Handbook (p153) it lists a vial of basic poison as 100 GBP and says that is only enough to coat one blade, or three pieces of ammunition. So not much bang for your buck. Worst of all it does a measly 1d4 damage – and that’s only if the victim doesn’t succeed a DC10 constitution check. Considering that it takes an action to apply the poison in the first place, this is underwhelming to say the least.

The Dungeon Master’s Guide attempts to come to the rescue (p. 257 and 258) with a more detailed list of potentially deadly toxins, although all of them are fantasy poisons that retail at outrageous prices (I would have preferred some poisons from the real world at sensible prices). The most attainable is Serpent Venom, harvested from giant poisonous snakes and retailing at 200 gp a dose, which does a respectable, if rarely deadly, 3d6 damage – although again the saving throw DC is just 11. You’ll need to pay ten times the amount (ie a whopping 2000 gp!) to get a dose of venom worthy of the name in the form of Purple Worm Poison which does 12d6 damage, with a saving throw DC of 19.

The ingested poisons, for slipping into someone’s cider glass, are priced similarly, and make you wonder why you couldn’t just administer some hemlock or rat poison for a fraction of the price that might in addition do the job it is intended to do. Something like Assassin’s Blood, 150 gp, does a paltry 1d12 damage and is saved on a DC10 anyway. Hardly your toxin of choice for a high profile hit job. (It is at least one of the few poisons that gives the victim the actual condition of being “poisoned”. According to p292 of the PH: a poisoned creature has disadvantage on attack rolls and ability checks).

Finally the rules for harvesting poisons are perhaps the most ridiculous… you can read them yourselves (DMG p258) but in most cases you are more likely to do damage to yourself than harvest a lethal dose.

Overall you are probably best speaking to your DM about what poisons you have access to, and what are the rules that govern using them. Laying low creatures with every nick of your blade is obviously going to make your character massively overpowered, but at least semi-frequent use of toxic materials should be part and parcel of playing an Assassin IMHO. (Remember as well that poison won’t work on many creatures like undead, demons and supernatural beings, whilst as a DM I would always give large creatures advantage on poison saving throws as obviously it’s exponentially harder to bring down an Ogre than a kobold with a nasty dose).

If there’s any shout for it, I might even create some new poisons for 5e D&D. Let me know if that you would interest you in the comments!

Your Equipment

As a Rogue you start with Leather armour, which is a bit of a joke as it only gives you 11AC instead of 10 with no protection whatsoever. Real life leather armour is actually really tough, so not sure why WOTC nerfed it for 5th edition. Anyway it only costs 45 gp to upgrade to studded leather, giving you AC12, which is sadly as about as high as you’re going to get for armour alone – luckily your dex. modifier as discussed is your best friend and you should have minimum 16 dex / +3 modifier to start with.

Armour aside you also get a Burglar’s Pack (p.151 of PH), which contains, I quote: a backpack, a bag of 1000 ball bearings, 10 feet of string, a bell, 5 candles, a crowbar, a hammer, 10 pitons, a hooded lantern, 2 flasks of oil, 5 days rations, a tinderbox and a waterskin. The pack also has 50 feet of hempen rope strapped to the side of it. Plus Thieves’ Tools (p154 of PH), which contains, I paraphrase: a small file, a set of lock picks, a small mirror mounted on a metal handle, a set of narrow-bladed scissors, and a pair of pliers.

The ballbearings can be useful to aid an escape… see also caltrops (both p.151 of the PH). I would definitely add a grappling hook to your list of possessions and maybe a wrist sheath, from which you can surreptitiously pop a knife/dagger in case of emergency. If you can dig out the old 2nd edition Thieves Handbook it had a load of good ideas to supplement your equipment with the likes of marked cards, loaded dice, blinding powder, weaponblack and more. Discuss with your DM what they might allow.

Don’t Miss This Feat!

Generally speaking when you have the chance to go for an ability score improvement or a feat, you’re going to want to take the chance to add another +2 to your Dexterity. As this will increase you modifier by +1, and that modifier goes on your AC, your attack rolls, your initiative and many skills checks… however there is one feat that is well worth selecting in my experience. And that is Alert. It doesn’t sound too sexy at first, its main boon being a +5 to initiative but when combined with your high dex. it pretty much guarantees you will always act first in combat, often allowing you to kill a foe before they have time to strike. Indeed, let’s read again the wording of the Assassinate skill which says: you are deadliest when you get the drop on your enemies. You have advantage on attack rolls against any creature that hasn’t taken a turn in the combat yet. In other words you can use Sneak Attack even without sneaking if you act first. (Of course it’s much better if they are surprised because: any hit you score against a creature that is surprised is a critical hit . Remember, in the case of surprise you would be getting your Sneak Attack anyway, but with Assassinate it becomes a critical Sneak Attack, meaning you roll ALL your damage dice twice, then add any modifiers).

I can’t really emphasise how much acting first is an advantage for a Rogue so select this feat and find out for yourself. The only other tempting feats for the Assassin are Sharpshooter and Lucky, the latter of which is banned on our table as it’s like having three inspiration points a day. Which is plain silly.


What’s more deadly than an Assassin? An Assassin that can radically alter their own appearance, create an illusionary diversion, make guards magically fall asleep or even turn themselves invisible. Whilst most Wizards don’t want to use their precious spells slots on utility spells, preferring to stake their authority in combat with the likes of Thunderwave and Fireball, there are dozens of 1st and 2nd level spells that perfectly compliment your roguish abilities, making multiclassing as a Wizard a fantastic option for optimising your gameplay.

Using the Prestigitation cantrip you could snuff out a candle, before closing in for the kill in a darkened room. Or on the battlefield you could use Misty Step to appear behind your opponent, granting you advantage (at the DM’s discretion), and therefore Sneak Attack bonuses on your strike. Need to beat a hasty retreat from the palace? Grease, Fog Cloud or Web will all slow down those pesky guards… or select my personal fave way of exiting the building by jumping out of a top floor window and casting Feather Fall as a reaction on the way down. Also worth noting, the easily neglected Shield spell is a life saver, literally, for combat situations and can also be cast using just a reaction.

More Inspiration

Hopefully this article has got you excited about playing a 5th Edition Rogue Assassin. Don’t cop out of roleplaying by opting for the “silent killer” mould though… use my tips to come up with hitman with both personality and power. If I haven’t got your creative juices flowing yet then why not take some inspiration from some of fiction’s best loved assassins, like Nikita, Leon, Altaïr ibn-La’Ahad, 007, and many more. NerdMuch have a list of eight of the best, whilst you can find a pretty comprehensive list on Wikipedia.

I will be back soon with the stats and personality of my own dagger in the dark, Xenia “Night Sting” Zanetti together with a profile of the guild she works for: The White Scorpions.

Is Counterspell Overpowered? How To Deal With Counterspell as a DM…

Is Counterspell overpowered? The answer is probably yes. Using just a reaction (ie. you can still use your own action to cast another spell or attack!), and a third level spell slot (minimum), you can negate the effect of any spell of 3rd level or lower cast within 60ft of you, and you have a decent chance of bringing higher level spells to a grinding halt as well.

During a recent encounter our poor Dungeon Master grew quite frustrated as the sorcerer in our party rendered a high level cleric powerless, by negating a succession of dangerous spells that would have put the combat right in the balance, all with just a couple of 3rd level spell slots. Maybe that’s why DM David voted it one of the four most annoying spells in D&D!

Counter this beeactch... (Artwork by Biffno on Deviantart)

Counter this beeatch… (Artwork by Biffno on Deviantart)

As a Dungeon Master the spell carries a double annoyance. It can make it harder to judge how tough to make encounters (if Fire Storm takes effect the party is going to be in a lot of trouble… if it doesn’t it could turn into a cakewalk), and from a story point of view it can replace epic happenings with the empty hiss of arcane magic fizzling out into nothing.

Of course you could simply ban the spell from the table, but that can feel pretty rough on those who consider it a key weapon in their armoury, so let’s look at some ways you can legitimately prevent it from getting overpowered without changing the existing rules.

1. Perception Check
The caster of Counterspell has to be able to see the caster of the spell they are trying to interrupt. But let’s remember that they don’t get a little notification in their inbox saying “someone within 60ft of you is trying to cast a spell, would you like to try and counter it?” Just because it’s possible for character A. to see character B., ie. there is a clear line of sight, doesn’t mean that character A. was looking in that direction at exactly the right moment. Unless the character in question was unquestionably focused on the caster have them roll a Perception check to see if they notice what the hell is going on. On a chaotic battlefield with multiple casters I’d recommend a DC of around 15.

2. Otherwise Engaged
I think it’s very fair to argue that even if the potential Counterspeller (as I will refer to them) can see a creature casting a spell, if they themselves are locked into a separate melee, they are likely to be much too busy dodging that mean-looking ogre’s spiked club to stand any realistic chance of foiling spellcasting in another section of the battlefield. If however a character is adamant that their main mission is to counter a creature’s spell, whether some other minion is blocking their path or not, you could make them roll DC 12 spellcasting ability check to see if they can react to the situation or not.

3. Don’t Automatically Reveal What Spell Is Being Cast
If you know one or more of your players has Counterspell up their wizards’ sleeves, then be smart. Don’t declare what spell your NPC is casting. Simply inform your player(s) that they see a creature (if indeed they do see them… see points 1. and 2.) about to cast a spell, and have them roll an Arcana check DC15. If they pass they correctly guess the spell being cast, otherwise they have no idea and have to gamble whether or not to use their spell slot to try and counter the spell on what might just be a magic missile or cantrip. What’s more if the character has never seen the spell cast before give them disadvantage on their Arcana roll (if they have seen it plenty, or frequently cast it themselves, you should probably give them advantage). If you want to be really mean roll for them privately, behind your screen, and feed them misinformation when they fail their roll. This way they never know for sure, because even when they pass the check and you tell them the truth, they don’t know they passed the roll, so can’t be sure to trust their character’s assessment.

4. Make The Players Act Instantly
The uncertainty caused by point 3. will create a lot hesitation… snap your fingers, and if they haven’t decided tell them they’re too late! They just lost their reaction. Better luck next time. (That is if they survive the Lich’s Power Word Kill… mwah ha ha ha!).

5. Get The Rules Right
When the spell being cast is higher than the spell slot being used to interrupt it the Counterspeller must make a DC check of 10 plus the spell level. They can add their spellcasting ability but NOT their proficiency bonus. (I mention this because we got this wrong on our table and indeed our frustrated DM might have got off at least one more spell if we had this clearer! There is actually a skill called Improved Abjuration available to Wizards who follow the School of Abjuration who reach 10th level that enables them to add their proficiency bonuses to this roll [p.115 of the Player’s Handbook]… chances are your players don’t have that!).

6. One Reaction A Turn Max.
Remember the spell does take a reaction. And every character only gets one reaction a round. So if they’ve cast Shield already for example, or indeed another Counterspell, or used Uncanny Dodge to halve some damage (if they are multiclass Rogue), then they’re shit out of luck.

7. Fight Fire(ball Extinguisher) with Fire(ball Extinguisher)
One other very obvious way to fight the power of Counterspell is to arm all your NPCs casters with it as well – a particularly good tactic if you want to persuade magic using characters on your table to drop it from gameplay altogether, as you’ll soon see them get frustrated when their own spells fizzle out and the combat is decided by the fighters in the party. (Do note however, despite some DMs arguing that you can, you can’t Counterspell a Counterspell. Aside from the ridiculousness that would ensue, that would also involve casting two spells simultaneously, which is not only against the rules, but also against common sense. Additionally CS is so fast there’s no way you could react to it… most spells take several seconds to cast, CS takes a split second).

Hipster Rules Fix

If, after applying all these factors to your gameplay, you still feel that the spell is overpowered let me suggest the following rules fix. Instead of setting a DC, the CS caster must contest the original caster each using their spellcasting ability modifier. If one of them is using a higher spell slot than the other, they get +2 modifier per slot higher.

Eg. Gandalf is a wizard with Intelligence 18 (+4 spellcasting modifier) and seeing the dastardly Harry Potter (Intelligence 16, +3 modifier) preparing a nefarious incantation he successfully rolls Arcana to recognise it. It’s the level 7 Finger of Death spell! Gandalf uses his highest spell slot left, a level 6, to try to counter it. He rolls a 15, which becomes 19 with his spellcasting modifier. Harry rolls 13, plus his own spellcasting modifier of 3, and an additional plus 2 as his spell is one level higher than the slot being used to counter it. His total is 18 (a draw would result in the spell being cast). Gandalf succeeds in his counter… just.

In my rules fix there’s also no such thing as an automatic counter, so you should roll/contest if even if you are countering a spell using a higher spell slot, getting +2 on your roll per slot level higher you use. (Otherwise a higher level wizard would systematically destroy a lower one without a chance, which is against the spirit of D&D).

Personally I quite like Counterspell, probably because I currently play as a multi-class Fighter / Rogue / Wizard, and it gives me a chance at least to avoid seriously nasty spells of magic users before engaging them in melee, where I have the upper hand. As someone with a long history of failing saving throws I really enjoy getting a second chance to avoid some excruciatingly annoying effect that is going to take my character out of the game for the rest of the encounter…

Plus this guy has some good advice on making it fun!

The Hipsters Play Curse of Strahd…

Last month we played the final session of a campaign that our Dungeon Master, Juan, had adapted from the official Curse of Strahd adventure published by Wizards of the Coast, especially for The Hipsters.

This was my first time playing an official D&D adventure and I really loved it. From my perspective it seemed like it gave the DM the perfect backdrop for running the campaign, giving him lots of great material and scenarios to work with, and the way he adapted it to our existing storyline worked really well.

watch curse of strahd online dnd session

He came from the fog…. (Photo sourced here).

In our storyline, after Suzail, the capital of Cormyr (in the Forgotten Realms setting), was destroyed by the Demon Lord Orcus, a letter arrived from a mysterious lord called Edgar Markov (Count Strahd in the official version of the story), who claimed to have defeated Orcus and only wanted the hand of the Princess Silva in marriage as reward. This all sounded pretty suspicious so The Shadowdale Allstars (as I like to refer to our group of adventurers) went to check out wtf was going on. The ever reckless Nada, a 10 year old fighter/rogue/warlock, decided to smuggle the Princess into our party as she was desperate to sneak a peak at this Lord who she may or may not be marrying. Bad idea, as pretty much the first thing that happened when we entered the cursed, fog-drenched land of Barovia, was that Markov appeared and used his considerable Vampiric powers to steal the poor Princess from us…

one of our first episodes was an encounter with a fortune teller who divined our futures with the help of some tarot cards – the results of which gave us each a destiny to fulfil within Barovia, and a perfect excuse to explore this evil land

An open assault on Castle Ravenloft, Markov’s haunted home, would have been reckless, whereas the magical and nefarious fog meant that was no way of returning home for reinforcements. We were trapped in Barovia, in what was to be “a sandbox adventure”. A sandbox campaign is one in which players are dropped into an environment and given a free run of what to do, without much prodding or leading by the nose from the DM (as opposed to a railroad adventure, when players are led by cause and effect from one encounter to another, with little room for deviating off track… I’ll discuss the pros and cons of these two styles in another post!). The Achilles Heel of any sandbox campaign is that the players can lack any motivation or goals, but one of our first episodes was an encounter with a fortune teller who divined our futures with the help of some tarot cards – the results of which gave us each a destiny to fulfil within Barovia, and a perfect excuse to explore this evil land. Whether it was to find a magical item, enlist an ally, or discover the Count’s personal secrets, we had plenty to do, and it was up to us how we went about doing this and in what order – with the overall goal of powering up enough to take on and defeat Markov and rescue the princess (if she wasn’t [un]dead already).

The Hipsters do battle in Barovia...

The Hipsters do battle in Barovia…

This made the game very satisfying from a playing point of view, and one reason why purchasing an adventure like Curse of Strahd can be money well spent. As a DM usually its hard enough to create all the details of three or four encounters that will make up a gaming session, let alone plan for the possibility of dozens more that giving the players a free rein could entail. But with an entire region mapped out in detail, the DM could give us a huge amount of freedom to explore, and if we didn’t happen on a particular episode as planned then it’s not the DM’s own work that goes to waste (which trust me is very painful!), it’s Chris Perkins‘ and hey we paid 50 dollars for the book so that’s fine.

On top of having all this material ready to go in any given session, the quality of the material is first class, with evocative descriptions, well-fleshed out NPCs and, best of all, really engaging encounters – aside from the aforementioned tarot readings, playing regional politics with werewolves, squabbling with gypsies and deciding whether or not to accept “dark gifts” in the Lich’s library were all really satisfying. I’ll no doubt buy the book myself and review it from a DM’s point of view at a future date, but as a player it gets two thumbs up.

the quality of the material is first class, with evocative descriptions, well-fleshed out NPCs and, best of all, really engaging encounters

Anyway I decided to film The Hipsters as we played what turned out to be our final gaming session in Barovia. We had actually met and defeated Markov the session before, killing him in an intense battle in the village, but, having discovered and read his diary, we knew we would have to journey to Castle Ravenloft and find the coffin where he regenerates after death, and finish him off for good. And that’s where these videos start…

As the session was nearly 9 hours long (including some downtime), I split the recording as I went along into five parts. I’ve never filmed anything before, so there’s some gaps, and mistakes, but overall you can get a good picture of how we play and hopefully it’s some fun footage to have in the background if you’re a fellow D&D addict like me.

Critical Fumble Tables for 5e D&D

What happens when you roll a 1 for an attack roll in Dungeons & Dragons? Well according to the official 5th Edition rules, not too much.

“If the d20 roll for an attack is a 1, the attack misses regardless of any modifiers or the target’s AC.” (p194 of the Player’s Handbook).

So you automatically miss, no matter what your attack roll modifier is and no matter how easy a target your opponent is, but nothing bad happens to mirror the powerful effects of scoring a critical hit when you roll a 20 (when you do double damage to your foe, and – at the DM’s discretion – also roll on the Lingering Injuries table – p272 of the Dungeon Master’s Guide).

That’s a bit boring frankly speaking! As far as I’m concerned a “critical fumble” blasts open the door of opportunity for something funny, unexpected or challenging to happen to both PCs and NPCs/Monsters, and every DM worth his salt will want to seize this opportunity to spice up a combat. Making up details on the fly can be challenging (a DM has plenty to think about as it is!) and can even make PCs feel victimised if they bear the brunt of an ad hoc ruling – leading to tedious arguments and/or an unhappy player. But, by having a clear table that applies to 1s rolled on attacks by both players and monsters, not only can you depend on some interesting outcomes for your D&D combats… but hey you can blame it all on the dice!

Dammit, not again...

Dammit, not again…

So without further ado, here is Hipsters & Dragons very own homebrew critical fumbles chart for melee weapons (with separate charts for both thrown and fired range weapons underneath). Just buy me a beer sometime!

Critical Fumbles Table (Melee Weapons)

Roll a d20…

1-2. Weapon Break. The force of your blow, or parrying that of your opponent’s, causes your weapon to snap in two. (For magical weapons roll an additional d10, on a 1 they break).

3-4. Goodbye Fair Blade! Roll an Strength / Athletics check DC 15, or your weapon flies d12 feet out of your hand in a random direction. If you have any movement and a bonus action left you can go and pick it up. In doing so you provoke an opportunity attack from anyone in the area, starting with your most immediate opponent. (Otherwise you could simply draw a second weapon, if you have one, using a bonus action).

5-6. Wild Swing. You overextend yourself going for the kill. Your opponent gains advantage on their next attack roll.

7. Stuck Weapon. Your weapon gets stuck in your opponent’s shield, armour, hide, or else in a tree or wall, or the ground. Roll a Strength check to see if you can free it using a bonus action. The DC is 8 + your strength modifier.

8. Ooops! You hit an unintended foe in combat. Randomise all combatants within 5 feet and roll a second attack roll, if you beat their armour class roll damage as if they were your intended target. (Discount sneak attack damage for Rogues).

9. Self Inflicted wound. You manage to slice yourself with your own blade, roll normal damage and half it. (Applies to combatants using slashing weapons and flails only. Other weapon types roll again. Discount sneak attack damage for Rogues).

10-14. Slip Up. You lose your footing. Roll Dexterity / Acrobatics check (DC15) or fall prone. Your turn has ended and melee attacks have advantage on you (see p292 of PH for conditions of being prone).

15. Pulled Muscle (Arms). Roll a Constitution Saving Throw DC15 or the strain of your attack causes you to pull a muscle in your upper body. You have disadvantage in attack rolls and ability checks requiring upper body strength until you have completed three long rests, or received magical healing.

16. Pulled Muscle (Legs). Roll a Constitution Saving Throw DC15 or the strain of combat causes you to pull a muscle in your leg. Your movement is halved, and you lose your dex modifier to AC and initiative, and you have disadvantage on any ability checks that require lower body strength, until you have completed three long rests, or received magical healing.

17-18. Loss of Nerve. Man your opponent looks tough. Make a Wisdom Saving Throw with a base DC of 10 modified by +2 for every hit dice higher than you your opponent has (or -2 for every hit dice less). On a fail you are frightened (see p292 of Player’s Handbook). After one turn you can attempt the saving throw again.

19. Broken Item. In the hurly burly of combat, something fragile – like a magic potion – you’re carrying breaks. Randomise fragile objects you have in your possession and roll to determine which. (Note, better to do this when the combat is over).

20. A Little Accident. Either through fear, excitement or simply needing to go, you soil yourself. 75% chance it’s only pee.

Critical Misses Table (Shooting Range Weapons)

Roll a d20…

1-2. Weapon Break. Your bow shaft or a mechanism in your crossbow breaks and is now useless. (For magical weapons roll an additional d10, on a 1 they break).

3-5. String Break. Your bowstring snaps. It takes 15 minutes to restring it.

6-8. Loose String. Your string comes loose. You lose this attack. Starting next turn you can make a sleight of hand check DC15 to fix it. Each attempt takes one turn.

9-16. Ooops! You hit an unintended random target. Randomise all combatants within 10 feet (for a short range attack, or 30 feet for a long range attack) and roll a second attack roll, if you beat their armour class roll damage as if they were your intended target (discount sneak attack damage for Rogues).

17-18. Ammo Accident. Your quiver spills (50% strap broken, 50% you tilt it over by accident), and the remainder of your arrows / bolts fall to the floor. If you remain still you can use a bonus action to pick up one a round and still fire using your action. Otherwise you can use an action to pick up 2d8 and put them back in your quiver.

19. Pulled Muscle (Upper Body). Roll a Constitution Saving Throw DC15 or the strain of your attack causes you to pull a muscle in your upper body. You have disadvantage in attack rolls and ability checks requiring upper body strength until you have completed three long rests, or received magical healing.

20. Slip Up. You lose your footing. Roll Dexterity / Acrobatics (DC15) or fall prone. Your turn has ended and melee attacks have advantage on you (see p292 of PH for conditions of being prone).

Critical Misses Table (Thrown Range Weapons)

Roll a d10

1. Weapon Break. The impact of your weapon hitting a tree, the ground, a shield etc. causes it to break. It is now useless. (For magical weapons roll an additional d10, on a 1 they break).

2. Pulled Muscle (Arms). Roll a Constitution Saving Throw DC15 or the strain of your attack causes you to pull a muscle in your upper body. You have disadvantage in attack rolls and ability checks requiring upper body strength until you have completed three long rests, or received magical healing.

3-4. Slip Up. You lose your footing. Roll Dexterity / Acrobatics (DC15) or fall prone. Your turn has ended and melee attacks have advantage on you (see p292 of PH for conditions of being prone).

5-9. Ooops! You hit an unintended random target. Randomise all combatants within 10 feet (for a short range attack, or 30 feet for a long range attack) and roll a second attack roll, if you beat their armour class roll damage as if they were your intended target (discount sneak attack damage for Rogues).

10. WTF? You launch a comically bad projectile attack nowhere near your intended opponent – it flies into a huge empty space (or at DM’s discretion a distant unintended target) taking your self confidence with it. Roll wisdom saving throw DC15, or suffer disadvantage to attack rolls until you next score a hit on an opponent.

Critical Fumbles for High Level Characters. Once your PCs have two or three attacks a round, they might start rolling an incongruous number of fumbles, especially for heroes of their ability. Whilst being a higher level should also make passing some saving throws / skills checks easier, as well as reduce the chance of weapon breaks (as most high level characters fight with magical weapons), if you feel it’s necessary you could bring in a new rule. Starting at Level 5 you could give them a fumble saving throw where if they roll their level or below on a d20 they suffer no adverse effects. That way extremely high level characters will rarely fumble. Or you could rule that only if they roll a 1 on their first attack of their round do they have to consult this table. Rolling a 1 on any other attack and it’s just an automatic miss.

Like this? I’ve got a few other homebrew rules that you might like as well. If you have a chance to play test any of them do let me know in the comments. Would love to hear from you…

Update, what happens when a monster with natural weapons, such as bite, claw or tail attack, rolls a 1? Here we go….

Critical Misses Table (Natural Weapons)

Roll a d10.

1-2. Ouch! The attacker snaps one or several teeth / claws on its target’s weapon or armour, or nearby surface. They receive 1d3hp of damage, and furthermore they must subtract the result of the same d3 roll from damage done from this attack from now on. (Ignore for tail attacks).

3-5. Wild Swing. The attacker overextends itself going for the kill. Their intended target gains advantage on their next attack roll.

6-7. Slip Up. The attacker loses its footing. Roll Dexterity / Acrobatics check (DC15) or fall prone. Their turn has ended and melee attacks have advantage on you (see p292 of PH for conditions of being prone). Creatures with more than two legs are immune to this effect.

8-10. Loss of Nerve. The attacker is scared. They must make a Wisdom Saving Throw with a base DC of 10 modified by +2 for every hit dice higher the target of the attack has vs. the attacker (or -2 for every hit dice less). On a fail they are frightened (see p292 of Player’s Handbook). After one turn they can attempt the saving throw again. Creatures that inspire fear are immune to this effect (unless their target also inspires fear).

Using Skills Without Proficiency (5e D&D)

Can I use a skill that I’m not proficient in?

According to the letter of the rules, yes you can. Page 174 of the Dungeons & Dragons Player’s Handbook states:

“Proficiency in a skill means an individual can add his or her proficiency bonus to ability checks that involve that skill. Without proficiency in the skill, the individual makes a normal ability check [adding just their ability modifier].”

Remember your proficiency bonus is the one that goes up as you gain levels. It starts at +2 at level one and is added to all skills checks your proficient in, as well as to attack rolls with weapons you’re proficient in. Check p15 of the Player’s Handbook for a table that shows proficiency bonuses next to character levels.

Your ability modifiers are the bonus (or minus) you get depending on your ability scores in strength, dexterity, intelligence etc. They are added to every ability/skill check you make.

To be 100% clear two first level Rogues, Vince and Howard, are walking across a tightrope above a yawning precipice. They both have dexterity 16 giving them an ability modifier of +3 each. But furthermore Vince has the acrobatics proficiency, meaning he can add a further +2 to his roll to make a total modifier of +5. Whilst Howard, who isn’t proficient, will have to hope +3 is all he requires!

skills and proficiencies

I’ll be fine with just my ability modifier Vince

This rule works pretty well for skills that most people could reasonably attempt at least, like climbing and jumping (athletics), riding a horse (animal handling), foraging for food (survival) or telling an outrageous lie whilst looking someone right in the eye (deception)… however for me it falls down when we talk about more technical skills, or ones that require specialist knowledge.

For that reason, I’ve created this small rules fix which declares several of the D&D skills as “technical skills / proficiencies”. When attempting to use these skills non-proficient characters not only don’t add their proficiency bonus but they attempt any checks at disadvantage.

Hipsters & Dragons list of “Technical Skills”

  • Arcana
  • Religion
  • Medicine
  • Thieves Toolkit
  • Disguise Kit
  • Poison Kit

All of these skills require a degree of specialist training and knowledge that, for me, need to be reflected in terms of probability when a non-proficient character uses them, and which I do by imposing disadvantage. The average fighter is not going to have a clue about arcane or religious rituals, not does he have the anatomical knowledge or herbal lore to have any realistic chance of performing any healing (medicine) on anyone other than bandaging wounds. (In fact I think it would be justified under many circumstances if the DM gives a non proficient no chance at all in tests of these skills). I will also place on the list:

  • Performance

With the caveat that non proficient characters can still have a decent bash at singing, storytelling or delivering a great speech… however they can’t just pick up a harp at a royal wedding and expect to impress the princess. (Most players will instinctively know this and roleplay accordingly anyhow… but hey show them this post if they disagree!).

Finally I will add that within the non-technical skills, as a DM I would still consider giving disadvantage to non proficient players for some more specialist skill tests. In fact my tightrope example above is a good one in this regard… whilst it makes sense that every character can attempt to forward roll over a tavern table without proficiency in acrobatics, walking a tightrope is a very technical skill, so a tough-but-fair DM (my favourite type) could easily justify imposing disdvantage. Similarly if you attempt to Crocodile Dundee a Buffalo and you’re not proficient in animal handling, I’m going to give you disadvantage (on top of a very high Difficulty Class… p.174 Player’s Handbook).

Improved Grappling Rules for 5th Edition

So here’s a question for any Dungeon Masters out there… have you ever pit your adventurers against an awesome and powerful foe and looked forward to the epic battle that was going to ensure between them… only for one of the characters to shout out on round one of the combat “I’m going to grapple him!”

One lucky roll later and your supposedly awe-inspiring NPC is restrained by a weedy 1st level halfling rogue whilst the others rain blows on his motionless ass, making short work of him.

(Image by Janus on ddemotivators).

(Image by Janus on ddemotivators).

The 5e D&D grappling rules have a lot to be desired in my opinion, and are also pretty vague. For a start the condition of being grappled (p290 in Player’s Handbook) states only that the subject cannot move, however most players will expect some kind of advantage over an NPC they have successfully wrestled with. It would make more sense if the conditions of being restrained (p292 PH) were also applied to the grappled subject.

In short, I’ve come up with what I think are improved rules, which effectively reduce your chances to grapple in armed combat, when such circumstances would realistically make this very difficult indeed, but do make grappling well worthwhile in the right circumstances. I also made some slight tweaks, for example whilst it makes sense that you can avoid being grappled using Dexterity / Acrobatics, once grappled it makes sense that only Strength / Athletics will set you free (you can hardly cartwheel out of danger if someone is holding your ankles). These rules are a little more complicated than Wizard of the Coast’s but I am confident that they will improve your gameplay and help you create realistic scenarios that your players will understand.


When you want to grab a creature or wrestle with it you can use the Attack action to make a special melee attack, a grapple. If you’re able to make multiple attacks with the Attack action this attack replaces one of them.

The target of your grapple must be within your reach and can be the same size as you, one size larger than you (in which case you suffer disadvantage), one size smaller (you gain advantage), or two sizes smaller (disadvantage… it’s hard to grab a rabbit!).

You can choose to use one hand (at disadvantage), or two hands. You must drop anything in these hands in order to grapple. If your target is armed you provoke an opportunity of attack from your opponent. If this attack is successful you take damage and the grapple automatically fails.

If the creature is unarmed and / or they fail on their attack of opportunity you make an Strength (Athletics) check contested by the target’s Strength (Athletics) or Dexterity (Acrobatics) check (the target may choose which). If you succeed you subject the target to the restrained condition.

Escaping A Grapple

A grappled creature can use its action to escape. To do it must contest a Strength (Athletics) check with its opponent. Note that the original contest would count at the victim’s reaction, so if they have not used their action this round (ie. they were after their attacker in the initiative sequence) they may use it in the same round to try and escape. Alternatively they may try to attack (with disadvantage, see conditions for being restrained). If they hit their target (who cannot add their dex modifier to their AC), the grappler must make a Strength check with DC 10 + damage of the attack to maintain the grapple.

If the victim of a grapple fails to escape for three turns, including the turn they were grappled in, then they are considered to be incapacitated (can speak only).

Moving a Grappled Creature

When you move you can drag or carry the grappled creature with you but your speed is halved, unless the creature is two or more sizes smaller than you.


(Modified from Player’s Handbook p292).

  • A restrained creature’s speed become 0.
  • Attack rolls against the creature have advantage (also they can’t add their dex modifier to their AC), and the creature’s attack rolls have disadvantage.
  • The creature has disadvantage on Dexterity saving throws.
  • Spellcasters must roll DC 15 (modified by spellcasting ability) to cast spells that include more than verbal components (spells with only verbal components can be cast as normal).

Further Notes

Note that monsters with a different physiognomy to humans that naturally grapple in their attacks, such as giant scorpions, do not provoke an opportunity attack when trying to grapple.

Once a creature is grappled, a second person, with at least one free hand, can use their action to confer advantage on keeping the subject grappled, provided he moves before the victim in the initiative chain. (The DM may rule that a third person renders the victim incapacitated provided they are of the same size as the one being grappled).

A grappler may use their bonus action to attack their victim (with advantage, as per the conditions of being restrained) either with an unarmed strike or a weapon (in the latter only if they succeeded in grappling with one hand… which remember they do with disadvantage). This means however, if they were not already, that they are now grappling with one hand, and so contest any escape attempt in this round at disadvantage.

The person who is being grappled normally has disadvantage on their attack rolls (see restrained condition above), however if they attack their grappler with unarmed strike or short weapon (dagger or smaller) they can lose that disadvantage. The DM may rule that they need to make a sleight of hand check to be able to draw a dagger if they were not already carrying it. Suggested DC10.


Nada a 4th level fighter / rogue PC with strength 14 is speaking with Xenia (a 4th level rogue assassin with strength 10, dex 18), a mysterious half elf with a scarred face, in The Thirsty Goat Tavern. She decides she can’t trust Xenia and without warning jumps across the table to grab her. Xenia is alert so Nada doesn’t get a surprise, but the DM gives Nada first initiative for the round without rolling. She rolls 12 for her attempted grapple and has proficiency in athletics making a total of 16, but Xenia has proficiency in acrobatics +4 dex modifier rolls 11 and gets a total of 17, ducking aside as Nada goes flying over the tabletop, sending two flagons of ale flying. Xenia promptly draws her shortsword, stabs Nada (who the DM rules is prone) and then uses her move turn to run out of the tavern door. Here she runs into Grunder a half orc paladin PC who was guarding the door. He drops his sword and also tries to grapple her, using both his hands. Xenia now is armed though, so he provokes an opportunity attack – which unfortunately for Xenia pings off his plate mail, allowing him to go through with the grapple. Grunder has strength 18 and rolls a 15 (+2 +4 = 21)… Xenia rolls a 3 (+2 +4 = 9). She is grappled and subjected to conditions of being restrained. They roll for initiative and Xenia wins. She has a choice… contest the grapple using strength (athletics), as she can no longer use acrobatics. Or make an attack at disadvantage that might force Grunder to let go of her. As she isn’t proficient in athletics, she prefers her chances at making an attack at disadvantage. She has +6 to hit AC18 and luckily rolls a 12 and a 19. She deals Grunder a meaty 9 hp damage, meaning he has to make DC 19 to maintain the grapple. The lucky half orc rolls 13, which with his proficiency and str bonus is just enough. Xenia is still grappled. It’s then Nada’s turn to act and she leaps to her feet and attacks Xenia with her longsword with advantage dealing 10hp damage. Grunder then uses his bonus action to punch Xenia, again at advantage, dealing 5hp damage. Realising she’s in a bind, Xenia begs for mercy.

For an in depth discussion on grappling check this conversation out on Facebook that these rules prompted (I should add that many defended the original rules for their simplicity, and stressed that grappling is just for reducing the movement of your opponent). If you’ve had any issues with grappling or playtested my rules please leave a comment below.

What is Dungeons & Dragons? And How Do I Play It?

If you’ve heard the words “Dungeons and Dragons” a million times without actually having any concrete idea what it is, let alone how to play it, then don’t worry… you’re definitely not alone. Most people only have a very vague (and often wildly inaccurate) notion of what Dungeons and Dragons is at best; whilst the game’s abstract nature – most, or even all, of the game takes place in your imagination – makes it very hard for newcomers to understand.

Basically the rules meant nothing to me, because I didn’t have any context to understand the game. And probably you don’t either, in which case this post is especially for you.

I once had the same problem myself. I distinctly remember having a burning desire to play this game at 10 years old, but no one I knew could really explain to me what it was. That was until a friend’s older brother lent me the Player’s Handbook (the most important of the game’s core rulebooks) and a Penguin guide entitled: What is Dungeons & Dragons? Awesome! I got stuck in straight away, starting at the start, expecting it all to click within a few paragraphs. But it didn’t. I kept reading, and then re-reading, because I felt certain that I’d somehow missed that vital paragraph or page where the basic concept of the game is explained. Granted, the Player’s Handbook contained lots of seemingly useful rules and tables, and yes I could look up the price of a spear and see that it did 1d6 damage, which was all very well and good, but something crucial was missing… who is buying the spears? And why? Is it me? In which case, how many do I need? And anyway where is the board? Who are my opponents? How do I win the game? SOMEBODY PLEASE JUST FUCKING TELL ME!!!

Beginner's guide to dungeons and dragons

These are just confusing me! (Photo copyright Hipsters & Dragons).

Basically the rules meant nothing to me, because I didn’t have any context to understand the game. And probably you don’t either, in which case this post is especially for you.

What is Dungeons & Dragons?

The short answer is that Dungeons and Dragons is a roleplaying game.

A slightly longer answer is that D&D (as we nearly always abbreviate it) is the world’s first roleplaying game first launched in 1974, which has since become much more than just a game, but a mega brand spawning novels, kids’ cartoons, computer games and even Hollywood films

An even longer answer follows after the question…

What is a Roleplaying Game?

Many people think that roleplaying is so called because you roll a lot of dice. But in fact it’s called roleplaying, because you play a role. In other words you act out a part or character. Whether you gave it much thought or not, you’ve almost certainly taken part in a little roleplaying already yourself, most probably in French class when your teacher asked you to read the part of Pierre who is calling Claudette (Bonjour Claudette, ca va?) to ask her if she would like to go to the cinema tonight. Or maybe you’ve indulged in a little roleplay when your partner asked you to dress up as a police(wo)man and handcuff them to the bed for being a naughty little… well it doesn’t matter why exactly.

The point is that a roleplaying game involves playing a character other than yourself, and pretending to be that person for the duration of the game.

The point is that a roleplaying game involves playing a character other than yourself, and pretending to be that person for the duration of the game.

In Dungeons & Dragons you typically play the role of a heroic character, which we call a Player Character of PC for short. Nearly all Dungeons & Dragons games take place in a fantasy setting, ie. in a world that is similar to Lord of the Rings or Game of Thrones.

It’s worth noting that thousands of other roleplaying games besides D&D exist, and depending on which game you’re joining you could end up playing for example a detective in Victorian England, a soldier in World War II, a vampire in Imperial China, or possibly a paranoid fighter pilot in a dystopian sci-fi setting. There’s even a Star Wars roleplaying game.

Think you can pilot the Millennium Falcon?

Think you can pilot the Millennium Falcon?

Finally in this section, I guess I should also distinguish tabletop roleplaying games from live roleplaying games. Dungeons & Dragons is a tabletop roleplaying game, meaning that you don’t physically act out what your character does… you simply describe it. If you’ve ever seen anyone dressed up as a barbarian chasing other people with a rubber sword in a woods somewhere that would be a live roleplaying game. You’d never catch a hipster like me doing anything like that! (And if you did it would be during a zombie apocalypse in a small Spanish town).

I Still Don’t Really Get It!

I know, I know. It’s still not really clear is it? But we’re getting there…

To play Dungeons and Dragons one person needs to perform the role of Dungeon Master, the rest all play Player Characters… let’s start with them…

What is a Player Character?

So to elaborate in Dungeons & Dragons, the tabletop roleplaying game, you play the role of a character… almost certainly a heroic character, which you create (if you’re new to the game someone might create one for you). Your Player Character has a gender, male or female are generally the two most popular options; a race, which is where things get a bit more fantastical, as typical D&D races include not just humans but elves, dwarves, dragonborn, halflings and gnomes, and a class. You can think of class as a little bit like an occupation, and typical classes include fighter, wizard, priest, thief/rogue, barbarian and ranger. In fact pretty much every D&D character can be summed up in three words.

“Hey Duncan, what PC (Player Character) are you playing next Sunday in my Curse of Strahd adventure?”

“Hey Bob, I’ll be playing a female elf wizard.”

Additionally, depending on how you choose to build your character (there are strict rules that govern this, which is why it’s better to have an experienced player do this for you to begin with) you will have different strengths and weaknesses, as well as different abilities and skills. For example typically a fighter is strong and tough, is great with a sword, but they generally can’t cast any spells nor are they the guys you turn to when you need someone to sneak into a castle undetected… that would be the role of the Thief/Rogue who are not so strong or tough, but are great at climbing, sneaking around in the shadows and picking locks (useful skills in many of the games scenarios). Meanwhile a wizard generally has to avoid hand to hand combat as they are neither strong, nor good with weapons, but their array of spells can be deadly in combat or very useful in non combat situations.

A character sheet...

A character sheet…

Normally we write on a sheet of paper (or on a purpose built Character Sheet) all of our character’s skills and attributes and then refer to them whenever the game demands it, to help determine whether our player will be successful in any given situation… whether they are trying to track a bear in the forest, interrogate a prisoner, or shoot an enemy with a bow from 200 yards.

Once the game gets started it will be up to you to control your character, reacting to events in the game, deciding whether your PC attacks the ogres with a glint of madness in their eyes, hides behind a pillar until an opportunity arises to stab their opponent in back or runs away screaming for his mummy. You decide what your character does, but the dice – and your character’s abilities – decide their success in doing it. One of the fun things about D&D is that there is a lot of luck involved, meaning events are rarely predictable and often amusingly absurd.

Roleplaying is lifted from a game, and closer to an art form, when we develop our characters’ backstories and personalities, bringing them to life and inhabiting them according to their unique identity.

There is one more very important thing to note on creating and playing a character, that relates back to what I wrote earlier about playing a role. When I was a kid pretty much all I cared about as a D&D player was how many orcs could I kill in combat, but anyone over the age of 14 should view their character as much more than a collection of stats. Roleplaying is lifted from a game, and closer to an art form, when we develop our characters’ backstories and personalities, bringing them to life and inhabiting them according to their unique identity. Thankfully the latest edition of the rules makes creating three dimensional characters easier than ever before, by offering players a choice of backgrounds and lists of personality traits, flaws and bonds to choose from (or select randomly). Maybe like BA Baracus, your character is scared of water and declares “I ain’t getting on no boat,” every time your party need to cross a river (leading to a merry pantomime of his teammates constantly trying to slip some powerful sedatives in his pint of ale). Maybe your fighter is actually a pacifist, who is determined to see the good in people, and tries desperately hard not to kill even downright dastardly goblins and ghoulies (“they just need a second chance in life!”), before lopping off their heads only as a last resort. Maybe your priest is a playboy and nymphomaniac who has to beg his deity for forgiveness on a daily basis after indulging in the sins of the flesh by corrupting the nuns next door. Once you’ve got a firm idea of who your character really is, from his unique upbringing to his motivation and personality quirks, you’re ready to play the game on another level, interacting in character with your fellow PCs in what is essentially improvised theatre (still with some orc slaying in between to keep it spicy). I don’t think it gets much better in this regard than Force Grey having fun with each other in this adventure chronicled on Youtube.

Introducing The Dungeon Master… aka God

Everyone growing up has played board games or computer games, and its pretty obvious what they are and how to play them. There is an objective, clearly defined rules and strict parameters… for example if you’re playing Call of Duty you can move and shoot, and well that’s about it. The reason is the “architect” of the game only was able to programme a finite number of scenarios and he figured the only thing you’re going to want to do is kill the enemies so he made a game to fit those criteria, and didn’t bother giving you any other options. What makes Dungeons and Dragons so appealing to its fans is there are no limits to what you can do (or rather try to do, because if your character can’t fly then he will die when jumps off a cliff). And what makes this possible is The Dungeon Master. The DM is the “architect” of any given session of Dungeons & Dragons, aka God… he creates the world in which your characters inhabit and he describes the scenarios that your characters find themselves in, and with the help of the rules and the dice, he determines what happens when your character tries to do something a bit tricky, like hit someone with their sword or ride a horse through a raging river (you don’t have to roll a dice to open a book or eat a bowl of soup). And whilst sometimes we use maps and miniatures to help imagine the exact locations of characters, especially in combat, when it’s often important to know whether you’re 10 or 30 feet from a door, or whether a troll stands between you and the cave entrance, but generally speaking most of the action takes place in the DM’s and players’ collective imaginations.

Imagination is essential, miniatures are optional... (Photo copyright H&D).

Imagination is essential, miniatures are optional… (Photo copyright H&D).

Importantly the DM also controls all Non-Player Characters (NPCs), ie. any character in the fantasy world that is not controlled by one of the players. If the Player Characters (PC) meet a traveller on the road, or decide to speak to the local innkeeper, it’s the DM who relays how they behave and what they say. Similarly the DM controls all monsters and bad guys (often taking an unprofessionally sadistic glee in them thwarting, injuring or even killing the PCs). As you can probably tell by now the DM uses NPCs to stage much of the adventure and provide the challenges that make the game so much fun. A good DM will give his NPCs as much personality as the players have given their PCs and they will have their own way of speaking, character traits and motives.

Sessions, Adventures and Campaigns

A session of Dungeons and Dragons is the physical time a group of friends spends playing the game, typically a few hours on a Sunday afternoon. An adventure gets underway when the PCs (Player Characters) decide to take on a quest usually suggested to them by an NPC… for example the mayor of town offers the characters a pot of gold if they will journey into the hills to kill a foul giant that continually steals their livestock. Depending on the adventure it might typically take two or three sessions to run. A campaign meanwhile is a series of adventures which are related to one another, and take place in the same fantasy world. So carrying on from the aforementioned adventure, maybe when the characters kill the giant in his lair, they discover a magical item that, unfortunately, bestows a curse upon them… and so they set off on a second adventure to remove this curse. Usually in a campaign the players play the same characters (unless until they die, perhaps crushed by the vast foot of that giant, in which case they will need to make new ones with new histories – and then the DM will integrate them into the story). Campaigns can go on indefinitely, and indeed many do go on for years. During this time characters gain what are known as “experience points” which accrue after each adventure and enable the character to gain new powers and skills, and generally be a lot more badass. This is a lot of fun for players who enjoy seeing their characters progress from “have a go heroes” to perhaps the most powerful beings in the realm (although they will have to play for a long time for that to happen… there are strict rules governing how characters develop!). A good roleplayer may well factor this change of character status by altering the way his character behaves… perhaps they turn from idealistic young man intent on saving the world, to power-crazed politician seduced by his own status and a taste of the finer things in life.

Campaigns can go on indefinitely, and indeed many do go on for years. During this time characters gain what are known as “experience points” which accrue after each adventure and enable the character to gain new powers and skills, and generally be a lot more badass.

Preparing an adventure, let alone a campaign, in a fully fledged fantasy world of your own making is a massive undertaking for any Dungeon Master, and luckily the game’s publishers, Wizards of the Coast, not only publish the core rulebooks of D&D, but they also publish readymade adventures, most of which take place in a fantasy world called the Forgotten Realms. There are in fact several official D&D worlds, like Dragonlance, Greyhawk and Dark Sun, but the Forgotten Realms is perhaps the most detailed and has been developed as a D&D setting since the 1970s. Nonetheless many DMs, including myself, prefer to create their own worlds, as that’s kind of half the fun for those of us with too much time on our hands…

How Can I Get Started?

By far the best way to get started is to join a game of experienced players, which admittedly is not always as easy done as said. However if you search around on community websites like Facebook, Craigslist, Meetup, Couchsurfing etc. you might a group of people like you looking for one or two new players. Also gaming stores are often a meeting point for those who want to run adventures and these days of course it’s also possible to play online – sign up to Roll20 and look for a game to join!

For more details check my in-depth post on how to start playing Dungeons & Dragons.

Introducing Hipsters & Dragons…

Welcome hipsters, geeks and gamers to the inaugural Hipsters & Dragons post! I’m really excited to launch this blog and share some of my gaming know-how and experience with you guys, and hopefully as well be part of bringing roleplaying (and specifically my favourite roleplaying game – Dungeons & Dragons) to a wider audience.

I first started playing D&D back in the late 80s when I was a small boy (I’m 39 now!) and loved it so much that I carried on playing it right up until adulthood, ie. long after it was socially acceptable to do so. However I did eventually hang up my dice around the time I went to University – mostly through lack of time, but partially at least because playing Dungeons & Dragons wasn’t the kind of association I wanted at college when I was trying (very hard) to be cool and attractive to women.

…playing Dungeons & Dragons wasn’t the kind of association I wanted at college when I was trying (very hard) to be cool and attractive to women.

It’s a shame that roleplaying has such an awkward reputation in this regard, because, as I will no doubt repeat many times in the course of this blog, roleplaying is in fact primarily a social activity. The rules and events of the game are in some ways just a platform for a group of friends to get together and enjoy each other’s company whilst solving the game’s problems, making jokes, acting a little and of course enjoy sharing some food and beers. The elements of make believe and the innumerable rules (which aren’t that important actually) can make things a bit nerdy, but it depends a lot on your group and their approach to the game. The humour and camaraderie is about as nerdy as you are. At any rate if you’re having fun, none of that should matter, and I honestly believe that 90% of people would enjoy some kind of roleplaying game (there are many that exist in real world, historical or sci-fi settings if you hate fantasy) if they gave them enough of a chance and met with the right players who share their style of play.

Getting around for a game. (Photo by Wizards of the Coast.

Getting around for a game. (Photo by Wizards of the Coast).

The good news for secret or ashamed roleplayers out there, as well as curious onlookers, is that Dungeons & Dragons seems to be enjoying a huge renaissance at the moment, making it possibly even more popular than in its 1980s heyday. The game is being repeated referenced in modern culture, such as this episode of Community, in several episodes of Stranger Things, in the IT Crowd and Big Bang Theory, to name but a few. And whilst these references often contain a healthy dose of mockery at some of the peccadillos of the game, they do with a knowing fondness that feels much more of a tribute than a parody of the game. Meanwhile many celebrities are also championing the roleplaying cause (when once you felt they may have stayed shtum) and stars like Vin Diesel, Tim Duncan, Matt Groening, Chris Hardwick, Stephen Colbert and Kevin Smith have all “come out” as gamers. Such is the epic rise of D&D, that in fact I’m pretty sure it’s only a matter of time before roleplaying zones start to make an appearance in zeitgeist-sensitive bars, so that hipsters can roll dice whilst stroking their beers and enjoying a craft beer. I certainly hope that’s gonna happen anyway. It’s got to beat cereal cafes right?

The rules and events of the game are in some ways just a platform for a group of friends to get together and enjoy each other’s company…

This fantastic renaissance has been boosted by the publication of a 5th edition of the Dungeons & Dragons core rulebooks by the brand owners Wizards of the Coast (they bought it from TSR many years ago and also publish Magic The Gathering the card game). Without going into too much detail now, the D&D rules have changed many times since they were first published in 1974, and each edition of the rulebook has aimed to improve the way the game is played to make it more entertaining. A bit like a new version of Windows, sometimes the publishers have succeeded, sometimes everyone has groaned, clicked on uninstall, and stuck with the old rules. But certainly this new 5th edition of the core rules has garnered praise from nearly everyone for its (relative) simplicity and its emphasis on roleplaying through creating interesting three dimensional characters (rather than geeking out on complicated combat skills etc.). It seems everyone in the D&D community has got behind these new 5e rules, and Wizards of the Coast I believe on are their fourth or fifth print run by now as sales have matched reviews by going through the roof.

It’s an exciting time for D&D and for roleplaying in general and if you fancy joining the ride Hipsters & Dragons will be here to stamp your ticket and help set you on your way… no minimum height requirement. You can read a bit more about my personal relationship with D&D here and how I got back into it after a 20 year hiatus, or you can wait eagerly for my second post.

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