D&D Memes For When Scheduling Is The Real BBEG

Updated on December 28, 2025

I tried to coordinate a post-holiday session and immediately remembered the true villain of Dungeons & Dragons isn’t a dragon. It’s the group chat. D&D memes are basically therapy for anyone who has ever typed “what night works for everyone?” and watched silence spread like fog of war. That’s why we do a dump of DnD memes weekly.

It’s that weird dead zone between leftover ham and “new year, new me,” when your dice are itching in their bag and your DM is quietly building an encounter called “Everyone Cancels.” If you need a quick hit of tabletop humor, this gallery of DnD memes is your short rest.

25 D&D Memes For The Post-Holiday Return To Chaos

First up in these D&D memes: the vintage Wererats art. Why do they look like they’re about to invite you to a candlelit booth and curse you politely? Old school rulebooks had zero chill and negative HR policies.

Then there’s the wizard who chooses Deep Rectal Itch instead of Fireball. That’s not combat. That’s a war crime with spell slots. It also explains why your party can’t stay in any tavern for more than ten minutes.

The Vox Machina archetype chart is painfully accurate. Every table has a “missing person,” a “please hydrate,” and someone who would absolutely walk into a trap because it “seemed fine.”

Bad Santa representing the holiday scheduling collapse is a whole mood. You don’t lose fights in December. You lose the ability to align calendars, and then your campaign becomes a seasonal tradition like eggnog.

Also: the Natural 20 discourse. The Doctor Strange meme is right. A crit doesn’t let you seduce a king, invent flight, and overthrow capitalism in one Persuasion check. Read the rules. Or at least pretend you did.

The dice set stuck in a very private place is the kind of story that makes a waiting room go silent. Somewhere, a cleric is casting Lesser Restoration and avoiding eye contact.

Confusing a Lodestone with an Orb of Annihilation is how you speedrun regret. That’s the moment the DM smiles, reaches for the notes, and you realize you’re about to be deleted from the narrative.

The mutual scrying meme is my favorite flavor of awkward. Two powerful enemies staring at each other through magic like, “Oh. You’re also doing this. Cool cool cool.”

And yes, the retired level 20 shopkeeper is real. The “harmless old man” behind the counter is a walking TPK prevention system.

If you’re still rolling after these D&D memes, keep going with 38 Fantasy Memes That Feel Like A Side Quest, 30 RPG Jokes That Hit Like A Critical Fail, and 35 Nerd Memes For People Who Over-Explain Lore.

Phil M. is a seasoned meme editor who files tabletop chaos, tags dice-goblin energy, and deploys only the strongest crits.