Roleplaying is often characterized as “doing what the character would do”. This extends from actions to speaking, maybe there’s a funny voice, and we call it a day. That’s entirely suitable for corporate training or facilitating some kinds of therapy. It is not, however, at all useful for our purposes in the realm of gaming.
The roleplaying mentioned above is a technique. It’s basically acting. Roleplaying as a recreational activity is something far deeper and more interesting. It’s not a set of rules or guidelines. It’s not the voices, the gestures, or the stories. It’s the discovery of a character’s depth and truth, through decision making.
Roleplaying is about establishing a character and then figuring out not only their mannerisms and little flavor bits but also who they are as a person. As the roleplayer, you animate the lifeless framework of their stats and (brief!) backstory. You take it for a ride and see where the road might lead. When you do finally get to where you’re going, you look back through the lens of what that character has become and understand a little more about yourself and mankind in general.
The cornerstone of all good roleplaying is not the backstory. You could write 100 pages of backstory about your character : how he grew up on a farm and he hates wearing socks or eating potatoes because his daddy beat him with potato-filled socks that he then had to eat. It’s interesting and fun but, for roleplaying, it tends to be far too rigid and does very little to define the aspects of the character that you’ll actually use.
Instead, I would recommend spending time coming up with a personality that appeals to you. A personality is a simple way of acting and a general moral compass. Maybe you’re a flirty cat girl or a wisecracking old man. You could be a stoic soldier or a Robin Hood. What matters is that you have a personality that you’re interested in portraying for more than 3 minutes. Spend your time here. Imagine a character that is interesting at first blush. All the depth of the backstory will come later. You just need the outward appearance of somebody fun or intriguing.
If you can hear the character’s voice in your mind, see his face, or maybe just picture how he would fight, you know you’re on the right track. Don’t stop early. Don’t go too deep. You just need an image of a character that has a personality.
Note : Many first timers will choose an archetype. That’s fine. You’re an evil wizard and you do evil wizard things. Maybe the only face you see is Gandalf. This is entirely sufficient for getting involved. Follow the rest of this guide and you might even find there’s more to him than you bargained for.
The personality you’ve chosen is what I call theme. This front-facing aspect of your character is going to inform all the additional choices you’ll make throughout. For examples in this primer, we’re going to use a pirate. Pirates are easy for everyone to imagine.
With your theme firmly in your mind, we’re going to make a few basic decisions. These decisions are independent from lore and shouldn’t trip you up at all. You need a name, a hometown, and a goal.
Regardless of the setting, you can choose whatever name you want. People get named stupid things all the time. I won’t bore you with how many “Strider”s I’ve had in my DnD campaigns. We’ll choose a pseudonym : Scurvy. We’re just known as Scurvy.
In all but the most professional of settings, every single town in the universe is not mapped out. Saying you’re from Hazelfort on the river Baldwin is fine. You can decide what kind of place Hazelfort was and its general geographic location (North, East, South, West, near a river, near the battlefield during a war). We’ll be from the port town of Shamshir.
Lastly, we need a goal. This appears to be the tough one at first but you really have total freedom. Searching for objects or people, revenge, fame, treasure, and adventure are all fine goals.
Your goal should be strong enough to pull you out of your hometown. It should be big enough that it’s going to take a while. It should be small enough that you could actually do it.
One of my personal favorite characters is a thief that had his soul bound to a gold coin by a witch. He now searches for his coin among all the coins in the world. He could find it on the first day or never. He wants to handle the maximum number of individual gold coins, rather than amass an amount of wealth.
Another is trying to escape a pirate captain who he worked for but escaped. His motivation is to keep moving away from the coast at all costs. He would kill for it. For Scurvy, we’ll keep it simple and say he wants money.
Alright, we’ve got a personality, some minor details, and a goal. This is sufficient to start playing a meaningful character. Scurvy the pirate could easily become a long-term character that we would enjoy very much and learn a lot from. However, because we’re good roleplayers and the game isn’t until Saturday, we’re going to take a moment to flesh out some details.
A good DM will incorporate the details of your character into the game and the world. If you have a bad DM, you can still get a lot out of fleshing out your character but I would implore you to seek a better group or help your DM to improve. There’s a certain magic when your details start popping up and getting expanded on in ways that even you didn’t expect.
Scurvy is our pseudonym but choosing a real name adds another layer of depth to the character. He doesn’t necessarily need to be hiding it but it’s something not known by many. When he suddenly receives a letter or hears a call across a random tavern, “Theodore Larkins.”, you’ll have a delightful moment of surprise and whatever feelings are associated with your true name. This simply cannot happen effectively if you don’t add some details.
Adding too many details creates a feeling of rigidity. There’s no surprise to be had because every aspect of your character’s history is so well-documented. There’s no third cousin or childhood rival to pull in. This rigidity is the death of discovery. It’s the very antithesis of roleplaying itself. Don’t put yourself in this prison of misery and call it a rich backstory.
Moving on to our hometown of Shamshir, it’s important to define (vaguely) what kind of place it is or was. If Shamshir is a port that primarily trades with pirates, that’s an important detail and might tell us how we arrived on a pirate ship in the first place. If it’s the personal port of some major company or noble, this can leave little dangling hooks of lore for both you and the DM to hook onto in the future.
For our purposes, Shamshir was the underground nickname of a smuggling port. By day, the small village of Comb Cove traded in imports from foreign nations. By night, Shamshir traded in weapons. As a result, we know our weapons and their values. We also have a subtle calling card to other outlaws.
Fleshing out a goal is usually a simple matter of asking, “Why?”. Why do we want money? Is Scurvy just greedy and likes living it up? Is he building an army to fund an attack on the nation? Does he want to buy his own boat and become a captain?
Any of these immediately brings five other things into the imagination. Resist the urge to chase them all down but give yourself enough motivation to move through the world in a non-random way. Everything your character does will eventually lead them down a path to this end.
Good ol’ Scurvy dreams of being a noble. He thinks making enough money will let him buy his way into land ownership and become something of a proper warlord. He wants to become a warlord because he yearns to be respected.
The why is so important because it gives us that general moral compass I was talking about. Obviously, a pirate who grew up smuggling weapons and dreaming of being a warlord has no problem with murdering folks or stealing. If it results in money or warlordship, he’s pretty much on board. For now, that’s sufficient.
With the basics out of the way, you’re absolutely ready to play this character. You know his voice, his face, his goals, his history, and where his morals lie. You haven’t written a single thing down. You’ve just made decisions. As you do this process more and more, it will get faster and faster. Eventually, you’ll be able to just throw a personality into your mind and the rest of the character will develop instantly.
The next step is the actual roleplaying bit – the part where we discover who this character actually is; the part where you breathe life into Scurvy.
Throughout the game, your DM will face you with scenarios and you’ll be asked to “act how the character would” in response. I’ll take you through a scenario.
The party arrives at the appointed hour, in the appointed place. Two large, gruff men guard the door, while your contact welcomes you in and rolls out a map.
“The target is Lord Cadface McCaddington. His son and wife are in the house. Kill them if they’re in the way but Cadface is the only one that pays.”
A murdering pirate may be alright with a lot of things, but is he alright with murdering a kid for no money? Will he shut the whole project down, find a way to avoid them, or just go along because he’s soulless? Will he slaughter these folks for even suggesting it? These things are up to you but the answers are found within the character.
We use the personality as a cornerstone for the character because it makes this decision easy. Scurvy is a generally fun-loving and not openly murderous fellow. He’s not out stabbing folks for fun. All the lives he ever took were just him doing his job, pursuing his goals – folks that shoulda surrendered. He doesn’t want to kill the wife or kid but he’s fully willing to.
We never wrote down whether Scurvy considered kid-killing within the scope of his morals. We never expressly set an amount of money that would make Scurvy betray his own morals. We discover these things by making decisions from within the framework we built.
Going forward, we now have the detail that he’ll kill while on a job but not for fun. This may heavily conflict with some other detail. The DM might say the kid is abused or that we recognize him as one of our lost pirate pals. In real-time, we must evaluate the many details and determine what is a larger portion of Scurvy’s character.
Does he care more about his former crew or getting the job done? Each time you make a decision, the character becomes more clear. Three games into a campaign, you’ll have enough organically crafted history in the world that you won’t even remember character creation.
An often-overlooked portion of roleplaying is the retrospective. There’s this weird myth among folks that characters always act in accordance with their morals and backstory guidelines. The truth is that once in a while you’re going to do things your character doesn’t agree with for some very good reasons. That’s conflicting for a person.
My paladin swore an oath to uphold the law, but he’s working with an outlaw to recover an artifact. Scurvy does what he must to get the job done, but there’s just something about this girl. My Dwarf is dedicated to his Dwarven family but this amount of gold would allow him to move his wife and son to a better place and become a noble.
These conflicts are the big turning points in a character’s story. Don’t overthink them. Follow the flow. Make the decision and look back later. Exploring those feelings of shame, regret, or anger are the epitome of roleplaying and discovery. Don’t be too eager to transform a character away from their original intent but don’t be afraid either. This is where the real meat of roleplaying lies.
Let those negative feelings drive the character development even further forward. Have your Dwarf move his family out to a better place with enough money to last them for entire lifetime, and then have him find a way to atone before he follows. Let your paladin quit the church until he’s able to reconcile his conflict. These are the truly interesting character moments that you never see coming because roleplaying isn’t scripted storytelling – it’s discovery.
The retrospective is looking back on your decisions through the lens of the character. It’s weighing those mistakes and triumphs and establishing a narrative for their life. If that was the first kid Scurvy ever killed, maybe that was the moment he really committed to his warlord path and it’s the moment that made him the great pirate he is today. Alternatively, maybe he made friends with a paladin who gave him new perspective on the innocence of children and he swears to never do it again : his deepest shame.
Somewhat unrelated, a great way to get a handle on the retrospective is to play singleplayer RPGs (Oblivion, Divinity, Way of the Samurai) as a conspiracy theorist. Question how every single NPC knows what they know. Assume every offhand comment is meant with full seriousness. Decide that every randomly generated item in a box was actually specifically put there by the owner. String these events together into a narrative that makes sense, no matter how unlikely. This is your character’s view of the world. Through this view of the world, the entire story takes on a new face and everything is interesting in a new way. You’ll never look at Oblivion the same again.
If you play any character long enough, they will eventually reach their logical conclusion. They may still be fun to play or be so invested in the party that you could come up with a million reasons why they should continue on. However once they’ve cleared their goal and you’ve wrung all you can discovery-wise from their cold lifeless corpse, it’s time to put them up on the shelf as a good memory.
Playing a character past their prime has a few negatives. Firstly, you never get to go out in a blaze of glory or retire to a peaceful life as a farmer. You never get that delicious satisfaction of closure. You also risk developing an aimless character into an empty shell of their former self. Lastly, you deprive yourself of the opportunity to go and discover a whole new character.
I would strongly urge you to consider retiring a character to be a badge of honor. Most folks will never know the joy of a well-ended story, a complete life. I’ve seen far too many characters driven into meme-madness by their creators, in the name of retaining levels and loot. Please don’t go down this path. I want you to get as much out of roleplaying as you can.
When it’s time to put a character away, roll up a new guy and just tell your group the old character’s time is done. Your DM should bring your new guy in at the same level. The game should continue rolling along. If you have a good DM, they might even have the retired character continue to help the party through some unseen means. (sending supplies, passing secret messages, or smuggling goods, something contextual to how they retired)
Death can also be a beautiful way to end a character, if you’d rather they not be touched. It’s also fun to see the look on everyone’s face when you go down in a blaze of glory.
Metagaming is when you use your knowledge, as a player, to influence your character's decisions. If Sisa out-rolled you on the last loot that you wanted, it’s not OK to use that as character motivation to not bail him out of jail. If you, as a player, know that the stats of a falchion are better than those of a rapier but your character is literally a fencer, don’t switch. Play your character and leave the real world out of it.
On this same note, there will invariably be a character who gets involved with the bad guys. The thief will get bought off or the wizard will make a deal with a demon. They’ll keep it under wraps until the very last session and dick the whole party over. Your character will die – forever.
If you see it coming but your character has no way of knowing, you just have to let it play out. It’s the honest and most valuable thing to do. This is the clearest indicator between good roleplayers and bad ones : Can you let your character suffer when the player could have stopped it?
If the scenario played out according to the characters involved, don’t get mad at the players of those characters. They’re not trying to spite you specifically. They’re just going through this same process of discovery that you are. Take it as an interesting plot point and keep on rocking. Losing a character is almost always a grumpy matter but sometimes you gotta lose. The transience of life is a great lesson to learn from roleplaying.
At the same time, don’t do weird betrayal stuff if you’re not in a party that can separate the characters from the players. It’s not worth it and it actually does make you the asshole. It’s not their lack of roleplaying skill that leads to the problem. It’s your inability to engage in effective cooperative storytelling with the group you have. Don’t be that guy.
There comes a time in every roleplayer's life where they’ve made an honest mistake. Some portion of backstory they mentioned or some decision they made was so far out of character that it simply doesn’t make sense. It’s so bad that it impedes further discovery of the character because consistency was lost.
At these times, simply talk to your DM or the whole group. Explain the situation. Tell them the detail change. Any half-decent group of roleplayers will be fine with it. Any DM that says no to a lore detail change should call me directly on the cellular telephone so I can tell them to go fuck themselves.
This is just a basic primer. It was meant to address what I think are some of the most common rookie mistakes when folks get into roleplaying. More articles on specific aspects of roleplaying will be coming down the track soon. If you have questions, just hit me up on Discord. I love to talk roleplay.