Sometimes there’s a perception that stories from your own tabletop games are a bit like dreams—unless you were there to experience it, they’re not all that interesting. We here at Sidequest largely disagree; it’s why we started the Let Me Tell You About My OC series, and it’s why this month’s roundtable is all about the fun we’ve been having in our tabletop games recently. Share in our recent tabletop trials and tribulations below, and let us know what fun you’ve been having in our comments section!

Tell us something that’s been fun or exciting in a recent tabletop game!

Melissa Brinks: I’m usually the DM for my gaming group (which doesn’t stop me from playing a himbo cleric as well), which means I end up answering a lot of questions I don’t anticipate. “Where’s the bathroom?” “What color is their outfit?” “What kind of flowers are there?” and so on. However, we’ve recently started a new game DMed by someone else, and that meant I got to create a character! I did my best on his backstory, fully anticipating we’d have a fun time learning about him as the plot develops, but no: immediately—and I mean literally maybe five minutes into the game, I got questions about his luggage. How many? What color? What’s in them? I’m not even DMing!

I had few answers for these questions but I found it extremely funny. Never change.

Alenka Figa: My partner has been GMing the Pathfinder module Kingmaker for myself and a couple of our friends for about a year and a half now. I have the great privilege of playing Fylson Ianwarin, an enby stoner elf (Swashbucker class), who was just trying to start a small gay commune in the fey wilds and instead has founded a whole-ass society. Early on in the game, Fyl and the party collected a bunch of bandits and turned them into “interns.” Fyl’s favorite intern was Rylas, a spunky ace/aro twenty-something who they were training in swordfighting. Rylas, unfortunately, was killed by the roll20 dice roller during our first big boss fight. A heartbroken Fyl did a bunch of hallucinogenic moss after his funeral and then had a bizarrely lucid conversation with him, because it turns out that Rylas’ soul now lives in Fyl’s body and they are living a truly strange buddy comedy.

This whole two-souled deal is totally homebrew on my partner’s part and has been super super fun. She gets to throw weird twists at me, and I get to have Fyl react as only Fyl can. One of the most recent twists involved a bit of body horror. While trying to urgently relay information Rylas was sharing with them—Rylas is uh, a lot smarter than Fyl, who is kind of a thembo—Rylas spoke directly to the group, in his own voice, using Fyl’s mouth. I truly had no idea this was coming! The revelation that Rylas could sometimes control Fyl’s body was a total shock and was clearly meant to freak me out! But Fyl found it hilarious and immediately had Rylas use their arm to wave at the group, before busting up laughing. I think the whole incident got a “well… OK,” from my partner. I am really, really proud of that whole stupid moment.

An illustration of two mischievous-looking fairies holding harlequin masks.

The fey formerly known as Pox and Pilfer before Nola and her sister’s characters stole their names.

Kate Lyons: I’ve been a part of a different homebrewed Pathfinder campaign for just about four years now. Bels, my elven arcane archer, has been through a lot of highs and lows (which I’ve written about before). She’s been heading for rock bottom after (in brief) committing regicide against her own father, killing our healer after a failed Will save, dying in combat and being resurrected through painful black magic, and just generally being a bit of a punching bag.

In the last few months, she’s finally turned things around. During a battle with the campaign’s Big Bad Lich, she took down a black dragon mostly on her own. Afterwards, the healer kissed her and took her on a really sweet date (cheered on by our biggest shipper, Alenka). When she came home, she found a letter waiting from none other than Fyl (the same from Alenka’s Kingmaker game; they were childhood friends, it’s a long story), who she thought she’d never hear from again. It’s been a series of wins for a character that I’ve really loved playing, and these wins have helped sprinkle some bright spots into the last year or so of general awfulness that the real world has had to offer. It’s also the culmination of a ton of character arcs and plot lines that we had been writing as a group, which is its own special kind of rewarding.

Elvie Mae Parian: I’ve been playing Old-School Essentials Classic Fantasy with some folks, a very rules-light system with no expectation for heavy, developed backstories in a sort of world where you knowingly craft squishy characters and no one is safe. As a result, it’s also very easy to pop in and out of sessions with new rosters of characters as you please.

I’ve been playing a pre-generated character known as the Bonesmith, which may not be exactly what you expect: having a title only and no actual name, the Bonesmith is a clerical-type character that pretty much dedicates themself to the cult of “skulls, dentistry, and organ dirges,” focused on the hoarding end goal of collecting all sorts of bones to make one of the greatest shrines ever as an indentured servant to their skeletal god. It’s very goofy, and it was even goofier popping in late to one game and discovering another person was playing the exact same character. As a result, we just improvised our way through to justify both our existences as if we came from two different sects. There were numerous times where we would simply imitate and mirror the actions of our fellow skull sibling, such as following up one’s failed attack with a more successful one, yielding very funny results and bizarrely synergized scenes filled with bone puns galore.

Nola Pfau: I’m in the game that Missy GMs, and so is my sister, and what can’t be overstated is just how much we are always trying to do a bit. Two notable instances: While adventuring in the Feywild, Missy’s himbo cleric ate some food that had the random effect of making him sing everything. Meanwhile, there is an NPC there known as Doctor Myriati, but we could never remember her name, so we started calling her Doctor Bodyody. Cue a complicated series of events where my sister and I, through our characters, attempted to maneuver the cleric over to said NPC and asked him her name. And what do you know, the GM suddenly pronounced the effect had ended…

Another time, in our most recent session (again in the Feywild), our characters came up with the plan of messing with some fey tricksters who enjoy playing pranks on people. Our attempt didn’t quite go off, but the upshot is that now we have their nicknames—as in, those nicknames belong to us. I imagine this is going to go poorly for us in the future, but it was very funny at the time.

Melissa: I would like to clarify that my refusal to sing was a real, actual roll result. I also really didn’t want to sing.

An illustration of Intari, a purple-skinned tiefling, in a maroon suit. She is sucking a lollipop.

Intari, Nola’s tiefling warlock and the proud owner of two faerie names.

Have you ever drastically broken a game, whether by accident or on purpose?

Sara Davis: I am not an experienced tabletop gamer, but my college best friend started a weekly D&D game over Zoom early in the pandemic, and it was a fantastic way to feel connected while feeding our creative drives.

Early on in the game, my party pooled our gold at the Fantasy Costco and bought our mage the Ring of the Grammarian, which allows him to change one letter in one of his spells once per day. This must be either the best or the worst invention in the realm. We turned a nice lady’s sofa into a Vampiric Couch, and dragged it into her basement where it bit several hostile creatures. (Full credit due to our DM, who had to quickly roll up some stats and abilities for our new sofa friend.) We weakened a miniboss’s armor by exposing him to the scathing critique of a Flaming Gay. We got thrown out of a tavern, possibly for life, because the mage cast Dog Cloud inside. Dogs for days. So much barking.

Melissa Brinks: This isn’t recent, but the reason I’m not allowed to run Call of Cthulhu is that I let my players talk me into letting them have pet Star Vampires, and since I didn’t ask them to make sanity rolls the first time they summoned them (I forgot), it didn’t feel fair to ask them to do it later. They just had no-consequence Star Vampire buddies. All the horror was gone from the game after that. Whoops.

Elvie: In the last D&D 5E game I ran, my party was reaching a point where they were pretty much starting to accumulate pets in the form of pretty unusual creatures, like a Blink Dog. A Blink Dog is a canine-like creature that is able to literally “blink” in and out of existence as a means of teleporting and ambushing. Although not game-breaking per se, but just a rather clever observation of how things work, the Blink Dog would be used for things such as moving things out of the way, even the players themselves, and they have also used other creatures’ abilities they have grown friendly with to their benefit.

Nola: Most of the game-breaking stuff I’ve seen in action hasn’t really been fun, but I saw Caio Santos on Twitter point out that as of the release of Van Richten’s Guide to Ravenloft, you can have an Artificer infuse their hat as a bag of holding, then a party of small-sized Dhampirs can just… go inside of it. Dhampirs don’t need to breathe, so they can just live in there and jump out for fights. It is… absurd.

I’ve also always been fond of Pun-Pun The Kobold, from 3.5.

How do we feel about games within games?

Sara: My group plays a lot of mini-games. Four-fifths of my D&D group are parents with young children, so we sometimes only have an hour or two to play after the kids go to bed and before the parents do. On those nights, instead of pursuing our main adventure, we might do a riddle challenge or a duel or something, just so we can get a bit of experience and gold.

My favorite minigame was Fantasy Chopped—and not just because I won. In the kitchen of a wizard’s tower, we were each given a map of the cooking stations (cauldron, grill, cone of cold, etc.) and the rules for how many “moves” it took to use them and how many points using them would add to our score. We rolled for ingredients, and then had to decide on our own how to use our moves. I rolled nat 20 for entree and got The Meatless Meat of a Thousand Wonder Beasts, but I like to think it was my own cooking experience that took me and the side dishes I rolled (collard greens, liquid smoke, forbidden rice) all the way to kitchen champion.

Elvie: There have been many game-within-game moments across different systems I have both played and ran, often revolving around usually a basic card game or game of chance as a means of pushing the plot forward or as a puzzle.

I love Sara’s own twist on Chopped because it also reminds me how I have often had moments of cooking in games to move forward. The success of how good the meal was did influence how things would go there on out. I do consider these cooking sessions to be games themselves because it still depends on the results of the dice-rolling mechanic per step of cooking to succeed and produce a competent meal.

Alenka: In am also in the Pathfinder game Kate mentioned above, but I don’t play Fyl, I play the bugbear vigilante Young Mustard who is actually a halfling bartender named Ulrick (please don’t spill their secret, I am sharing this in confidence). We are in a downtime period between arcs and have celebrated a couple character birthdays, including Ulrick’s boyfriend Noyal’s birthday! I decided I wanted Ulrick to set up a fun day for Noyal, and the friend who plays him decided he was “a laser tag guy.” Laser tag is kind of hard to translate to medieval times, so we opted for paintball, 10 Things I Hate About You style! Our GM set up a whole thing where we had to navigate a little map and try to stealthily throw paintballs at each other. It was very silly and fun, and I loved playing Ulrick in that setting, because they are at a place of growth where they’re trying to spend a little less time as an intense, paranoid vigilante bugbear, and more time as their halfling self. I lost paintball, but it was great!

Kate: And I won paintball, so I also thought it was great.

Nola: I love them! As a GM, throwing a game inside of the game, or a puzzle, or riddles… all of that is spice. It shakes things up, keeps the game from being too rote or repetitive. They’re absolutely necessary.