Tabletop Roleplaying 101

7min read


You, or someone you know, has expressed interest in participating in some form of tabletop roleplaying.

What is tabletop roleplaying?

Tabletop roleplaying is a form of interactive storytelling. We’ve been telling each other stories sitting around a campfire for as long as anyone can remember. Tabletop roleplaying games are an extension of this. At their core, these games are all about people connecting with each other, creating shared experiences through play and discovering themselves by becoming someone else.

Tabletop roleplaying games provide the structure through which players can ease themselves into another world and fully immerse themselves in the characters they’re playing.

Tabletop roleplaying as we know it today got its start in 1974 when the first edition of Dungeons and Dragons (AKA DND) was published. The acronym DND has since become synonymous with “tabletop roleplaying” with quite a few people using these terms interchangeably.

DND has remained popular to this day (for better or worse) and brought an increasing number of players into the tabletop roleplaying world over the years (players like me).

DND was the system I was introduced to over a decade ago when I first got started roleplaying. It’s a “crunchy” system (as in number “crunching”) with a ton of rules which make it hard for me to recommend to a new player.

But, if you know some people who are playing DND and are open to you joining their group for a session to try it out. Go for it! It (probably) can’t hurt.

Wizards of the Coast (who’ve owned the DND license since the late 90s, and also happen to own Magic the Gathering) have molded DND into its current form to maximize profit at the expense of making a game that’s easy to learn and fun to play.

If you’ve ever wondered why a single game can have literally hundreds of different rulebooks, well it’s because the more books they publish, the more you have to buy (or want to buy to avoid “missing out”) and the more money they make.

Here’s a few other gripes I have with DND:

  1. The rules are spread out in a bunch of different rulebooks which makes it hard to play the game.
  2. The crunchiness of the rules makes it difficult to improvise adventures on the fly.
  3. The probability distribution of the legacy twenty-sided die used for important dice rolls makes it so you’re just as likely to be bumbling around with your pants on your head as you are to be accomplishing incredible displays of skill.
  4. A fantasy setting, unless handled carefully, can be boring to roleplay in. Being tropey and having a hard line between good and evil means that there’s not much opportunity for players to play in the space between.

Thankfully, it doesn’t have to be this way. There have (and will continue to be) many people seeking out roleplaying experiences outside of what DND can provide.

I’m biased against DND for the reasons described above but more than anything its focus on rules and number crunching leaves little room for collaborative storytelling (which is the part of roleplaying that I enjoy the most).

Doing math with friends isn’t compelling to me, no matter how I much like math and how much I like my friends. Collaborative storytelling is the reason why I go out of my way to regularly participate in tabletop roleplaying.

If you’d like to get a taste of a tabletop roleplaying system that focuses on collaborative storytelling rather than number crunching, I highly recommend Everyone is John.

Here’s the publisher’s pitch for it:

Welcome to Everyone is John, the curiously unusual roleplaying game where each player struggles with their own unique skill sets and personal obsessions. The catch? Each player is a unique voice in one man’s head. Everyone is John is a fast and fun competitive RPG where each player assumes the identity of a “Voice” inside the head of John - a man with no real identity of his own. John’s actions, skills, knowledge, and goals change constantly as the voices in his head vie for control of him by using their own finite willpower. Each voice will struggle to achieve their own obsessive goals before all Willpower is gone and the game is over - with only one Voice left as the victor. Everyone is John is a fast, fun game that lets players create their Voices in just a few minutes, and begin play right away. It’s the ultimate pickup RPG.

I’ve played Everyone is John a few times now, and it’s an absolute blast each and every time. It’s easy to learn and teach. It gets quite goofy and this works well with players who are new to roleplaying. It’s a great icebreaker and makes everybody at the table more comfortable being silly with each other (a key part of roleplaying).

If you’re looking for a system that’s a little more chunky, that you and your friends can play week after week after week, then look no further than one of my favorite tabletop roleplaying games: Blades in the Dark.

Here’s the publisher’s pitch for it:

Blades in the Dark is a tabletop role-playing game about a crew of daring scoundrels seeking their fortunes on the haunted streets of an industrial-fantasy city. There are heists, chases, occult mysteries, dangerous bargains, bloody skirmishes, and, above all, riches to be had — if you’re bold enough to seize them. You and your fledgling crew must thrive amidst the threats of rival gangs, powerful noble families, vengeful ghosts, the Bluecoats of the city watch, and the siren song of your scoundrel’s own vices. Will you rise to power in the criminal underworld? What are you willing to do to get to the top?

Why do I love it so much and why do I think you might too?

Everything you need to play the game is in one little book: the rules, the setting the game takes place in and a bunch of tips for playing the game and having fun.

The rules are focused on helping you tell interesting stories together (important) instead of telling you what number to subtract from your health points when a troll smacks you around (not important).

Blades in the Dark respects your time and allows you to skip over the tedious (like searching for traps every 5 minutes and preparing for every single bad thing that “might” happen) by allowing to go straight to the fun. If something unexpected happens that you wish you had prepared for, that’s fine, figure out how you prepared EXACTLY for this kind of situation and then fast forward back to the present and continue playing.

Blades in the Dark uses six-sided dice for everything and the way they are rolled makes for more interesting stories. When you roll dice to try and achieve some kind of goal (like punching a dude and knocking him out):

  • Most of the time, you’re going to succeed with a complication (you knock him out but you bruise your hand).
  • Rarely, you will critically succeed at what you’re trying to do and get more than what you wanted (you knock him out and you punch him so hard, he flies into his friends, who all get knocked out).
  • Rarely, you will critically fail, get nothing and have to deal with the consequences of that (you miss him completely, while you’re recovering he shoots you in the chest).

It’s expected that your characters are somewhat decent in everything that they do and, so, the dice rolls reflect that while leaving room for exciting successes and failures.

I could go on but I’ll stop there. Hopefully, I’ve been able to give you a peek into what I like about tabletop roleplaying and what you might eventually like about it too, if you make the right choice and get into it.

Roleplaying isn’t easy. It requires a substantial investment of time and effort. Before you know exactly what kind of roleplaying you enjoy and who you should be playing with, you might not always be having the time of your life.

But, eventually, when you’re playing the right game with the right people, everything just clicks and you’ll be having an absolute blast and you won’t be able to stop. I know that I can’t.

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