Hipsters & Dragons

Because roleplaying is social, creative, fun… and kinda cool!

Category: Tips for Players

The Assassin: Xenia “Nightsting” Zanetti

Let’s talk about my first ever 5th Edition character… one that has proved a tonne of fun to play over the last year or so, thanks to not only her roguish abilities (ie. sneaking around backstabbing unsuspected guards) but also her handiness in a fight and more recently her spellcasting ability, which I’ve used to cleverly (IMHO!) complement her efficiency as an agent of death.

Dear multiverse, meet Xenia ‘Nightsting’ Zanetti, a half-elven Rogue Assassin.

Xenia had it pretty tough as a kid. The unwanted daughter of an elf, raped by a human, she was left in a basket at a human orphanage with a bag of guilt-laced gold that didn’t make the orphanage owners treat her any better. They sold the pretty half elf girl for a tidy sum to an unscrupulous slave master with a lascivious eye. She was still a girl when the same master began paying her nocturnal visits. When one day she resisted his advances he smashed her face with an iron sconce, breaking her cheekbone and leaving a massive ugly gash under her right eye. She ran away, risking death, and lived on the streets, until she was found half dead in the gutter by an elderly man who would become her benefactor. Seeing something in this slim but fierce strapling, he enrolled her in a society that could help her… a society that specialised in just vengeance: The White Scorpions. Here she trained in the art of dealing death, surviving the terrifying initiation ceremony to become a fully fledged killer. Her training was complete with the termination of her inaugural victim, the slave master who had raped and abused countless times.

Particularly deadly at night, when her elvish dark vision comes into play, Nightsting (as she became known) subsequently infiltrated the Purple Dragons Army where she served as the captain of a unit of archers, before (and this is when I started playing her) being integrated into a party of adventurers known as the Shadowdale Allstars to spy on a suspicious Dwarven cleric called Leif. Leif has long since died, but the Shadowdale Allstars continue to battle the forces of evil, with Xenia by their side. She has never forgotten her allegiance to the White Scorpions.

Above you can see the stats for Xenia at 8th level, by which time she is 5th level Rogue Assassin and 3rd level Wizard. I’ve really enjoyed my decision to multiclass as a wizard because it opens up so many possibilities and allows for a lot of creativity in gameplay situations, be that combat or deception. Misty step is brilliant for positioning yourself behind an enemy in the blink of an eye… or for teleporting out of trouble, shield has saved my ass so many times, giving me AC 23 for one round when I really need it (and cast with just a reaction), I probably don’t need to sell you on the advantages of being able to turn invisible when required, whilst minor illusion (improved version I specialised in illusion) is perfect for distracting guards on those rare – but always crucial – moments you fail a Stealth check. The low level wizard spells are like a toolbox that help you do your job, as well as open up boundless new possibilities beyond hiding and sneak attacking.

Of course the more obvious option for those that want to play a spellcasting Rogue is to select Arcane Trickster archetype, instead of Assassin. The main advantage here being that you gain spells whilst still increasing your Rogue level, thus continuing to increase the damage you do on Sneak Attacks (as well as gaining other Rogue abilities). However you don’t get the all important Assassinate skill if you choose this path…

Seeing how effective magic has made Xenia I continued to level up as a Wizard until 10th level (5 Rogue / 5 Wizard) at which point she received two level 3 spell slots, enabling her to cast some pretty serious spells such as fireball, fly and counterspell. Major image is also handy if you bring a creative mind to it… summoning an illusory pit, wall, fire, monster or bridge can be pretty effective in the right circumstances.

Since then Xenia took advantage of a power vacuum in the Dalelands to become the Lord Commander of the Purple Dragon Army, and so for principally roleplaying reasons I multiclassed again, this time as a Fighter. She now wears specially tailored half plate mail suited to her new role in society, and now when she uses her bonus action to attack as a dual wielder she is able to add her Dexterity bonus to damage rolls as per the fighting style ‘Two Weapon Fighting’ (p72. of PH) – something which I appreciate a lot.

Ok, I hope this post wasn’t too self-indulgent… but perhaps if you’re thinking about playing a Rogue Assassin in 5th edition this has given you a few ideas. For a detailed look at how to build an effective PC of this class check out my previous post, where I look at what races, stats, proficiencies, feats and equipment I think work best, and discuss the importance of coming up with a coherent back story.

Want to avoid being one of those really irritating gamers and play an assassin of good alignment, who your party members can trust? Then no problems, the Order of the White Scorpions – to which Xenia ‘Nightsting’ Zanetti belongs – are an assassins’ guild compromising of fanatical vigilantes of top moral fibre. I’m putting the finishing touches to an ebook about the Order, which will be available to buy at a very friendly price on the DMs Guild soon! For the price of a coffee you’ll get the lowdown on this secret society, including recruiting and training methods, initiation ceremony, rules and regulations, a new poison, secret tongue and guild motto. Also included are a bespoke Background, plus adventure hooks for your DM to work your back story into their campaign.

Stay tuned!

New Spells for Wizards (& Others)

I’ve spent a lot of time this year preparing one of my D&D adventures for publication, an adventure that hinges around the Order of the Gossamer Robes, a pioneering body of wizards whose mastery of magic has allowed them to formulate many and various powerful news spells. Naturally, having created this storyline, I was duty-bound to create at least some of the incantations that these arcane academics have committed to their seminal tome, The Discoveries.

I will be releasing the adventure soon on DMs Guild, along with the full version of The Discoveries, which currently contains 27 new spells. As a little teaser – and also to allow for playtesting and feedback before publication – I’d like to publish six of those incantations right now.

My goal in authoring them was to provide some new effects and possibilities that currently don’t exist (or at least I have missed!) in the 5th edition Player’s Handbook (or else provide the same effects but in different ways). And whilst nominally wizards’ spells, I’ll leave it up to you if you feel that they could be adopted by sorcerers, warlocks or certain priests.

Hopefully I’ve pitched them about right. They need to be as useful / powerful as existing spells (otherwise why bother create them!? No one would learn them…) and yet not not so powerful they unbalance the game.

Bridge

2nd level conjuration

Casting Time: 1 action
Range: 60 feet
Components: V, S
Duration: Concentration, up to 10 minutes.

You create a shimmering bridge of energy 5 feet wide and 30 feet long, which arcs 5 feet above the ground at its highest point.
At Higher Levels. When you cast this spell using a 3rd level spell slot or higher the bridge you can create is an additional 5 feet wide, 10 feet long and arcing 5 feet higher for every extra spell slot expended. Additionally the duration of the spell increases by 10 minutes per spell slot used.

Author’s notes: I designed this so a low level wizard can solve problems in a dungeon, whilst a higher level one can help armies cross raging torrents…

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Chameleon

Illusion cantrip

Casting Time: 1 action
Range: Self
Components: V, S, M (a piece of chameleon skin)
Duration: Concentration, up to 10 minutes.

You assume the colours and appearance of the nearest surface, blending into your environment, enabling you to become all but invisible when still. The spell has no effect on any creature that has already seen you (unless you break line of sight and then hide), and the spell’s effects cease to work whenever you move.

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Flash Bang

3rd level evocation

Casting Time: Bonus action
Range: 60ft
Components: V, S, M
Duration: Instantaneous

You trigger a blast of magical force, accompanied by a thunderclap and flash of bright white light, that affects any creature within a 30 foot radius of a point you choose within range. The blast does 2d10 force damage, or half as much on a successful Strength saving throw, and causes victims to be stunned for 1 turn (no effect on save).
At Higher Levels. The damage increases by 1d10 for each spell slot level expended above 3rd.

Author’s note: Nowhere near as dangerous as fireball, the stun effect coupled with the fact it only requires a bonus action to cast I think make this spell interesting. Might be best used by a multiclass character, such as a rogue, who could then use sneak attack on the victims

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Lavinia’s Stunning Escape

5th level evocation

Casting Time: 1 minute (activated with a reaction)
Range: Self
Components: V, S, M (a pair of cymbals)
Duration: 24 hours

You weave a protective aura around yourself (or a willing target you touch) that you are able to trigger using a reaction the moment you take damage from an attack. When triggered a stunning blast of magical force affects anyone within 30ft, doing 2d10 damage (half on a successful Strength saving throw) and causing them to be stunned for 1 turn (no effect on save). In addition you may turn invisible as per the conditions of the spell invisibility (requires concentration, ends if you attack a creature) and teleport up to 60ft to an unoccupied space that you can see. The spell must be triggered within 24 hours of casting, or be lost. Only one protective aura can be active per person at one time, and it can be triggered only once.

Author’s note: an extremely powerful defence mechanism, this is a good spell to reward a PC with… possibly found in a musty spellbook in the depths of some dungeon (or in the Gleaming Cloud Citadel, if you buy my adventure out soon!).

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Meredin’s Mighty Applause

4th level illusion

Casting Time: 1 action
Range: 120ft
Components: V, S, M (a flower in bloom)
Duration: Concentration, up to 1 minute

Any humanoid within 30ft radius of the targeted creature of this spell must succeed on a Charisma saving throw or be overwhelmed by a need to clap this target, dropping whatever is in their hands to do so. This enthusiastic applause takes up the entirety of their turn. They may repeat the saving throw at the end of their turn.
The spell ends for an affected creature if it takes any damage.
At Higher Levels. For every spell slot expended beyond 4th level, the radius effect of the spell increases by 10 feet.

Author’s note: I feel this one could be a lot of fun – and very effective – in the right situation.

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Heart Attack

7th level necromancy

Casting Time: 1 action
Range: 30 feet
Components: V, S, M (a chicken’s heart, crushed when casting the spell)
Duration: Instantaneous

You wrap a spectral hand around the heart of a giant-sized target or smaller within range and squeeze. The target must make a Constitution saving throw, and then roll a d12 and consult the following table. If they pass their saving throw they may add 3 to the roll.

D12 Spell Effect
1. Heart explodes causing instant death
2-4. Heart collapses reducing target to 0 hp
5-10. Heart attack. Target is paralysed for 1d4 rounds, taking 4d6 damage
each round.
11-12.+ Target suffers excruciating heart tremors doing 4d6 damage.

At Higher Levels. When you cast this spell using a 8th level spell slot or higher you can target one additional creature per spell slot expended.

Author’s Note: I like spells with a little table of effects! I found trying to pitch the danger of a 7th spell really hard, so let me know how you get on with this one… comments appreciated!

Phobias for PCs & NPCs (5e D&D)

“I ain’t getting in no boat fool!”

Ever wanted to give your PC a little extra flavour, such as BA’s infamous phobia of both boats and flying, or Indiana Jones’ fear of snakes? The mightiest heroes have weaknesses and flaws, that make them all the more credible – and even heroic, since they often have to overcome them – and will lift your PC above the ranks of that tedious infallible paladin you usually play.

Every great hero has a weakness…

For those who love the roleplaying challenge of 5th edition Dungeons & Dragons, here is my table of common(ish) phobias that will ensure your character is no cookie-cutter hero but one whose Achilles’ heal can all too often place him and his fellow adventurers in grave danger.

DMs meanwhile, perhaps you want to use this when creating your NPCs? It’s going to be a hell of a lot harder to rescue that princess from the castle’s dungeons at night if she’s scared of the dark…

Hipsters & Dragons Table of Phobias (5e D&D)

Roll a d20

1. Fear of Darkness
2. Fear of Fire
3. Fear of Water (oceans, lakes, rivers)
4. Fear of Heights
5. Fear of Thunder and Lightning
6. Fear of Ghosts (and/or undead)
7. Fear of Death
8. Fear of Enclosed Spaces
9. Fear of Open Spaces
10. Fear of Spiders
11. Fear of Snakes (and/or lizards)
12. Fear of Insects (or biting / stinging ones at least)
13. Fear of Dogs or Wolves.
14. Fear of Cats
15. Fear of Rodents
16. Fear of Fish
17. Fear of Horses
18. Fear of Mirrors
19. Fear of Divine Magic (obviously reroll if you’re a Cleric, Paladin)
20. Fear of Sorcery (obviously reroll if you’re a Wizard, Sorcerer etc.)

How strong the phobia is, is probably best for you to decide. Strong enough to inconvenience you will make for good roleplaying opportunities. So strong that everyday adventuring situations become a massive and rapidly tedious pantomime is soon going to grate on your fellow PCs.

If you do want to randomise the extent of the phobia though I would suggest this table.

Roll a d10

1-7. Normal phobia. Of God, get it away from me.
7-9. Extreme phobia. Please no, don’t make me…
10. Crippling phobia. No fucking way Jose.

How Not To Be A Really Annoying Player

Beyond finding the treasure, rescuing the princess, and saving the village / town / nation / world, every game of Dungeons and Dragons has a higher goal… that everyone playing has fun. In that sense D&D is very much a team sport, dependent on the co-operation of all gathered. As such it can quickly be ruined, or impaired, by someone that doesn’t buy into the team mentality, usually because they want, consciously or subconsciously, for the game to revolve around them.

Just like a game of five a aside (ie. soccer to any American readers) can be spoiled by a Lionel Messi wannabe who attempts to take on the entire opposition and shoot every time he gets the ball, a game of D&D can quickly be compromised by a selfish player who monopolises the DM’s attention and tries to take control of everything from the party’s strategy and decision making, to NPC interactions and combat scenarios. Whether that Messi wannabe has the skills to back up their selfishness is besides the point (in soccer at least they invariably don’t!); because by their singular approach, this one person excludes the other party members from playing a full role, reducing them to spectators for much of the session.

Partly for cathartic reasons, partly for educational ones (feel free to subtly share this with any friends who are guilty of one or two of the misdemeanours below!) and partly to remind myself to improve my own gaming behaviour (as I’ve ticked off most of the below in my time!) I’ve compiled this list of specific things that players do which the game could really do without.

One type of annoying player… according to Dorkly.

So without further ado, let’s take a look. Which of these bad gaming etiquette traits are you guilty of?

10+ Things Annoying Players Do in D&D

1. Control Familiars, Pets, Steeds, Henchmen

For many it’s one of Dungeons & Dragons most loved spells, but my number one pet peeve in the game is the Find Familiar spell as it’s a massive time sink, especially in the hands of someone who constantly abuses it. Much of D&D is waiting for your fellow party members to act, and that’s fine, but when someone’s turn consistently takes twice as long to act because they are commanding their pet hawk / bat / cat / guinea pig / woodlouse to perform some additional task I start to think how much better this adventure would be without the animal in question. Familiars also are also a massive cop out for most adventurers, allowing parties to scout way too easily, possibly infringing on the Rogue’s role (see point 3. below) and perform a host of minor tasks without character involvement or risk. Worse still than familiars however are creatures that PCs control that get an attack. Do I really want to spend my precious Sunday afternoons watching someone roll dice to see if their warhorse or henchman scores a crappy hit? Unless it’s a solo campaign, no player should try to control anything other than his player… and no DM should allow otherwise.

2. Start A Fight At Every Opportunity

We get it. You’re a real tough guy. Everyone should be quaking in their boots the minute your half orc barbarian walks into the tavern with his two handed axe. You’ve written “quick to anger” on your character sheet just to make sure that it’s perfectly ok to start a fight at every single opportunity… except it isn’t. It’s really fucking dull, and it negates any opportunity for people with actual roleplaying skills to negotiate, charm, deceive, flirt, banter, or beguile with NPCs – which you may not realise it, is what some people actually most enjoy about D&D. Just because you’ve built a character for combat doesn’t mean you should reduce every D&D encounter to a combat situation as soon as possible (nor does it make you real world tough by the way, just in case you’re confused). For one thing it’s plain ridiculous. Even in more lawless times very few people drew swords the moment an insult was exchanged… and if they did they wouldn’t live very long. Nor would your character if I was DM. For another thing it is just plain downright selfish to those PCs with non combat skills. In every adventure I’ve ever played in 75% of encounters are combat anyway, so there’s really no need to bring the remaining 25% down to your level.

3. Usurp Others’ Jobs

Since the very beginning D&D was engineered to be a team game, with each player bringing something to the table, dictated to a large extent by which character class they choose to play. For sneaking around and disarming traps there’s the Rogue, for healing and turning undead the Cleric, for mass damage and special effects there’s the Wizard, and for hand to hand combat and sucking up damage there’s the Fighter. It’s part of what makes D&D so much fun, because – at least in a well balanced adventure – every character gets their moment(s) in the spotlight. There’s few things more frustrating then than the player who insists on performing multiple roles, especially if in doing so they tread on the feet of the other PCs. If you’re the party’s fighter don’t try to be the guy that sneaks round the back to take out the guard, even if you have Stealth proficiency: let the Rogue do his job. Similarly if you’re a Barbarian with Intelligence 8 don’t take advantage of the game mechanics and declare “I roll Arcana” the moment magic happens… let the Sorcerer or Warlock have their moment in the sun. Bear this in mind especially if / when you start multiclassing. I for example currently play an Assassin / Wizard, and whilst I do have Fireball in my spellbook, unless I’m predicting a particularly tough day in the office, I rarely prepare it, because doing mass damage to a rank of foes is the Sorcerer’s job in our party. Rather I use my spells to enhance my character’s role as the Rogue.

4. Constantly Call For A Roll (Especially At The Wrong Time)

This one annoys me both as a player and as a DM… a player interrupts proceedings to loudly shout “I roll Insight / Arcana / History” and then clatters his dice over the table with the expectancy of being told something on a high roll. First of all a player should never declare he is rolling, they are not the games master… they should start by asking the DM if it’s appropriate to roll a skills check. But first of all they should wait as long as possible to allow the roleplaying in question to pan out. If for example the DM, speaking as an NPC, is acting out a conversation with another PC in your party, then let them talk it out as much as possible and see if this NPC seems trustworthy by, you know, roleplaying. Rolling dice and demanding answers is the crudest way to play your characters, and certainly should never interrupt gameplay.

5. Don’t Accept That Shit Can Happen To Them

This annoys me more when I’m the DM, but it can come into effect as a player too if refusal to accept a bad outcome ends up in a lengthy argument between PC and DM that wastes gameplay time. If bad shit happens to your character accept it without too much fuss. Speaking from my personal experience, it can be really irritating when it happens to you, especially if you feel the DM hasn’t judged the situation well or enforced the rules properly, but ultimately a large part of the fun of D&D is the risk of your character dying, so certainly things like being injured, maimed or weakened should be water off your feathered back. If you want a narrative where your character succeeds every time at everything and is all powerful then stay at home and play with yourself. Certainly don’t get in a sulk and a protracted argument with the DM that wastes everyone else’s time.

6. Play Disruptive Characters (Then Justify It As “Roleplaying”)

If your favourite alignment is Chaotic Neutral then no need to wonder who the dick on the table is… it’s you. Chaotic Neutral is the alignment the worst type of players invariably choose because it allows them to do what the fuck they want whenever they want, without doing anything as difficult as roleplaying a realistic character. Instead they can just respond on a whim to situations in order to get the best advantage of themselves without abiding by any consistency of behaviour. In fact many Chaotic Neutral players will insist that their character’s dick moves are in fact testament to their brilliant roleplaying because stealing the ally’s magical weapons or starting a bar fight for no reason is exactly what a Chaotic Neutral person would do. What they fail to see is that manufacturing a character in order to give themselves carte blanche to be a dick is even worse than just being a dick. In general PCs that are disruptive to the the rest of the party’s goals are incredibly frustrating for fellow players and DMs, usually selfishly choosing their own sense of what’s entertaining at the expense of everyone else’s.

(Castles and Cooks say it best: you don’t have to pickpocket every NPC. The inn is perfectly fine without you setting it on fire. It doesn’t matter how “cool it sounds”… Betraying your fellow adventurers for the fun of it does not make you awesome. The name for this behavior is Chaotic Stupid, and it sucks).

7. Powergame

Powergaming is of course the practice of min. / maxing all your attributes, and selecting your skills and feats to be as powerful as possible, especially in combat. Whilst a little powergaming is rarely too damaging in itself, it’s often symptomatic of someone who is going to try to steal the limelight and do everything themselves. Someone who is trying “to win D&D” as if it were a board game. The real danger here is if someone, whilst sharing the same level as other PCs in the group, has managed to make their character grossly overpowered, then it may leave other players with less to do or feeling redundant. If you catch yourself powergaming either in the character creation process, or as you level up, then start to focus instead on who your character is instead, and determine your attributes and skills based on their personality and life story, not what is going to give you the best possible damage modifier in combat.

8. Cheat (By Actively Metagaming)

Metagaming, as I’m sure you know (if you read any roleplaying blogs), is when you act on your personal knowledge of the game’s rules and mechanics, above and beyond what your character knows. It’s almost inevitable to some extent, and it can actually be tedious not to metagame at times (for example it’s usually much easier to assume that something an NPC tells one PC in private gets relayed to the rest of the party than have to act out the charade every time it happens), but it can also be abused. What I would call “active Metagaming” should be strongly discouraged. This could be doing something illogical or outrageously out of character because it confers an advantage, when you know something your character doesn’t, or for example deliberately checking the Monster Manual in between sessions to find out a foe’s prepared spells or weaknesses. It is basically cheating and can take a lot of fun out of the game for everyone – including the person that does it.

9. Get Drunk / Wasted

(I have a feeling this one just applies only to my specific group of hedonists in Barcelona! Take note guys!). Just like playing football with someone who is struggling to control the ball quickly becomes really tedious, so is roleplaying with someone who’s crossed the line of being tipsy into drunk. Communication slows down, situations have to be explained again and again, there’s a lot of shouting over one another, and arguing with the DM, as well as a lot of reckless decisions that don’t make any sense in the context of the game and break the illusion of reality you have tried to create as a group. Tea on the other hand is awesome.

10. Mistake Themselves For The Dungeon Master

This often happens when one or more players know the rules better than the Dungeon Master in session, and therefore they constantly intervene to contradict and overrule said DM’s decisions. It’s perfectly ok to point out the rules from time to time, but often a DM makes a decision based on his judgement of the scenario that effect A causes effect B to happen, and trying to argue it doesn’t because you haven’t used your Bonus Action yet is all a bit petty and trite. A sense of logic and realism is always more important that the wording of the rules and, even if you don’t agree with the DM, it’s definitely not your job to arbitrate what happens, rulebook in hand. Furthermore players who constantly badger and petition the DM for breaks or situational advantages are almost certainly doing so to the detriment of the rest of the party, who are operating under the same circumstances but are polite enough not to spend the whole session whining / arguing about it.

No, no, and thrice no…

11. Take Forever On Their Turn

You know the scenario. Goblin arrows are raining from the sky, orcs are piling over the parapet, and a monstrous ettin is bearing down on the party, spiked club in hand. The heat of battle is furnace-like in its intensity, the time for action is now – there’s no time to think. Only one player is leafing through the Player’s Handbook for the best possible spell to utilise. No not this one. Maybe this one. What’s the range again? Then he suddenly remembers his new feat could come in handy. Or is it a 5th level character ability? I’ll just look it up. Cue eyerolls. You know what instead of a normal attack action I’m going to use acrobatics to [insert outrageously improbable trick] and appear behind the ettin so I get advantage on my roll. Just to get it over with the DM consents and the player’s turn is finally over… surely? Wait, I still have half of my movement left and my bonus action! Please God, make it stop! Ok and now it’s my warhorse’s turn. He breaks free of his reins in the stables and bursts into the courtyard and tramples on the nearest orcs as he makes his way towards me…. If you recognise yourself reading this, please change yourself! Whilst considering your options in combat is one of the fun dilemmas of any D&D session, there needs to be some respect for time both in terms of realism (snap decisions!) and basic respect for your fellow gamers. Meanwhile memorising your commonly used spells and abilities can save a lot of faffing around during the time-limited Sunday sessions you and your friends have to play D&D.

Agree with this list? What other annoying things do characters on your table do? What is the best way to discourage them from doing them in future?

Apart from avoiding the above, I’ll be back with a list of awesome things you should do to make yourself a better gamer very soon!

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

Backstory

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!

UPDATE: I just published an e-book on the Order of the White Scorpions on DMs Guild. You can buy it for just 2.99 USD and I hope it will give you a big headstart on fleshing out an awesome character.

Now available to buy on the DMs Guild…

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.

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

Bond
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.

Flaw
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!

(By the way, my e-book on The Order of the White Scorpions does include a new background ‘Trainee Assassin’ which would suit anyone wanting to play a character groomed for the killing game from an early age).

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 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. After level one it’s completely pointless.

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 semi-respectable 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!

UPDATE: I do include playtested rules for a new poison in my aforementioned e-book. Deathstalker Scorpion Venom is an injury poison, a concentrated dose of which brings on temporary paralysis (on a failed save) allowing its administrator to dispatch their victim.

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.

Multiclassing…

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.

A reminder that you can find 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 on this very blog.

You can even power up your PC, give them a tonne of extra credibility and support the handsome, kitten-saving, environmentally sustainable and downright loveable – but very poor – guy behind Hipsters & Dragons by buying his e-book.

>>> Buy The White Scorpions Assassins Guild for 5th Edition Dungeons & Dragons <<<

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