Every Game Master (GM) probably has compiled a list in their minds of the most traumatizing moments in their illustrious GMing careers. The moments they look back on and go, “Yeah, I did not see that one coming”. Whether it’s a disaster you should have anticipated but didn’t, a player ploy too ludicrous to foresee, or a series of actions too baffling to preemptively contemplate, all GMs eventually find themselves mentally screaming into the void. Here’s a list of three GM “Oh Fuck” moments; may you learn from past mistakes. 

1. Devil Deals

So here’s the scoop: I’m running a game for myself and four friends. As is typical for anyone trying to run a D&D game in college, at least two of them quit on me every week for some reason or another. But I have one consistent player (hi blogging partner) who made a character, Dale, with an interesting GM hook: Dale made a deal with the devil to become a warlock and lost his memories of what he sacrificed as part of the bargain.

Some cool stuff no? Some infinite realms of possibility? Some wonderful drama?

Unfortunately, it was an extended one-shot (three sessions about 3-4 hours each), so I really didn’t have the space to go into a deep dive of any character’s backstory. I had some vague ideas about Dale based on what backstory information the player gave me and that was about it. I figured the pact wouldn’t matter much in the overall game.

Skip to the end.

Dale and the others have fought their way through the fey realm, retrieved a McGuffin (aka magic item) from the claws of a dragon, and hopped into a seriously shady portal opened for them by Dale’s sponsor, the fiend. Great. They arrive back in the material realm, they have this ultra-powerful item, and the demon needs it to escape its prison and start the next demon Armageddon. (As you do.) Now, this has gone swimmingly! I think to myself. They are exactly where I want them! The whole party (minus the one person doing homework) debates what to do with this item. And just to make things more dramatic (you can never have too much drama) the demon tells Dale this: give me the orb and you shall have whatever favor you desire.

Is it cheesy? Yes. Is it still ridiculously fun? Absolutely. So I was thinking (like the foolishly lawful good GM I am) that Dale isn’t going to strike a bargain. Maybe bluff a bit, exchange quippy dialogue, but obviously he wouldn’t want a demon released from prison. He’s a good person. Right?

Right?

So imagine my horror when Dale goes, “I’ll give it to you if you return my memories to me.”

And cue the moment in a GM’s life when you feel your game combust and plummet to the ground. What is in those memories the demon took? No idea. Hadn’t planned for it. But when you’re in the GM hotseat, you can’t just say you don’t know. You make it up. But if I make it up (and bullshitting is my expertise), then Dale gives the demon the McGuffin. Then the demon escapes and cue total party kill (TPK). It’s a fucking scary-ass, high-level demon. Like. It’s going to betray them. They’re level five. They will not survive this. 

Well. What to do?

Now from the demon’s perspective, this is like, the best deal ever. The demon gives the mortal (Dale) his memories back, receives the McGuffin, breaks out of its prison, and wreaks havoc on the universe. What kind of self-respecting demon would say no? But what kind of GM ends the session on a TPK because the rest of the party is distracted while Dale unleashes a supernatural apocalypse? 

I needed time. So naturally, I aimlessly rolled some dice (sometimes your GM is rolling to stall, fun fact.) I told Dale (something like), “Swear to me you shall deliver the item immediately after I complete your request and I shall grant you that which you desire.” Dale (like a cheeky bitch) goes: “I will on the condition that you can only use the item when I allow it.”

Oh boy. Dale, why didn’t you include a “and don’t kill me” clause? There are so many loopholes. Example A: Demon agrees. Boom, memories. Boom, item. Boom, demon kills everyone. Boom, demon apocalypse. But I really didn’t want to end my session with a TPK. And I had not expected Dale to actually bargain with the fate of the world. Like. Yikes.

So the demon quibbles about the terms and session ends with Dale flying off, McGuffin in hand, no memories restored.

But honestly. That demon should’ve taken those terms. Like. 100% taken them. Looking back, I probably should have just unleashed the demon. But I hadn’t prepared memories or demon stats and it was the end of the last session.

So that’s what happens when you don’t expect your players to actually make a deal with the devil. (Pro tip: always expect your players to make a deal with the devil.)

2. Drinking Problems

If you’ve ever played Call of Cthulhu, you know it’s a great system for investigation, intrigue, and horror. I was running a campaign that was very…time and space-y. Basically the entire thing was an excuse to have a samurai, a priest of Apollo, an 18th century teenager, a WWII Russian sniper, a 1950s Russian spy, and a 17th century English sailor adventure together. It was a hot-mess of a game but it had many memorable moments, including the sailor successful stealing laundry in front of an entire town only for the samurai to rat him out, the sniper discovering a magic item that turned her invisible and proceeding to wreak absolute havoc, and an inexplicably Irish barkeep in an Italian town because Yours Truly panicked at the thought of attempting an Italian accent. But the moment I will never forget? When the 18th century teenager drank a nymph. 

So here’s what happened: the party arrived in a Renaissance Italian city and attempted to locate an inventor for Plot Reasons (yes, I’d recently played Assassin’s Creed, sue me). Their investigations led them down a well and (because I’m a drama llama) into some partly submerged underground ruins. There they learned that a BBEG, otherwise known as the Big Bad Evil Guy, had (for Evil Reasons) poisoned the nymph dwelling within the ancient Roman ruins. Her compromised essence poisoned the city’s water supply. 

Hijinks ensue and the party ends up with a dying nymph on their hands after she uses the last of her power to cleanse the city’s water. She makes a last request to the party, begging them to transfer her essence to a large, clean source (like a lake) where she could rejuvenate. She then basically turned into a puddle. (Don’t ask me how any of this makes sense, frankly there were more plot holes in this campaign than in swiss cheese.) Anyway, they stuck her in a flask for transport (classy).

The party then exited into the city’s cathedral, which caught them off guard. The twenty or so armed men pointing crossbows at them also caught them off guard. 

Essentially (through the bullshit blah blah power of plot convenience), the BBEG ambushed the party and prepared to dump the dying nymph on the cathedral floor, killing her. There’s nothing they can do to stop me, I thought to myself. This will be their warning not to underestimate these guys.

Then the player with the nymph-in-a-flask turns to me. “The human body is made of 60% water,” they say. Now call me a little slow on the uptake but I was like, “Yeah and?” 

“I drink the nymph.”

Yeah. I didn’t know how to respond to that. I still don’t know how to respond to that. The next few minutes are a blur to me, I think my brain short circuited. But there were some rolls and (long story short) my player successfully drank a nymph. 

 What does that even mean? Is the nymph possessing them? Is the nymph in their digestive tract? Can they sweat her out? Does her essence leave via some other less savory means? I don’t have the answers to this mystery and frankly, I’d like to keep it that way. 

3. I Can’t Go on Your Adventure

Quick disclaimer, this happened to a friend (another GM) and not me. But the story is fucking gold (and basically a legend in our gaming group) so I’m going to tell it here. My friend is running a Warhammer Fantasy one shot (I was sadly busy and couldn’t attend) with our usual crew and a new guy. The New Guy, the hero of this story, managed to kill his character in the first ten minutes of the game and set a new group record.

Let’s start at the beginning. My friend gives the players free reign to make their characters but adds one caveat: they need a reason to go on an adventure. Maybe to gain gold and glory. Maybe to find a lost harmonica. Maybe to spin a better tale when bragging at the local Inn. Whatever the reason, just have it prepared. Sounds simple enough. 

You’d think.

Alright, the party is assembled at the Inn (classic). And New Guy is playing a jailor. (Interesting choice but okay.) First thing he does upon entering the Inn? Push a halfling, the character of another player, off a stool and sit there. (We like to call this “a red flag”.) Party cohesion is off to a good start. The New Guy additionally states that his character hasn’t slept for three days. The GM warns him the character will suffer exhaustion points for it. The player disregards the warning. (This comes up later.) Well, when the quest does turn up and the rest of the party decide to go (you know, the one requirement), the jailor says, “I have a cushy life here and a jail that needs guarding. I can’t go on your adventure.” 

Needless to say, at this point the GM is reconsidering her life choices. The rest of the party begins the adventure and the jailor returns to his jail. Well, the GM thinks to herself, no matter. I can find a way to pull him in. So she turns to him while the rest of the party RPs and asks him what he’s doing. Turns out the player wasn’t fancying the severe game penalties for not having slept in three days. After berating the prisoners (and continuing to make many friends), he decides to take a nap. The GM, thoroughly befuddled by this out-of-body experience, asks where he goes to sleep. 

“In a jail cell”, he adds. 

“Okay, an empty one?” 

“No. The one with the dwarf in it. I’ll put the key outside the cell so he can’t reach it and take a nap.” 

So he goes to sleep in a jail cell. With a prisoner in there. Whom he just berated. With the keys just outside of arm’s reach. 

The GM, at this point, just wants to insert some logic into the lunacy. So the prisoner, not being an idiot, decides this is an excellent opportunity to escape. He attacks the sleeping jailor and subsequently kills him after a brief skirmish. Then, using the jailor’s weapon, reaches the key and initiates a mass prison break. 

The other players continue on their adventure.

The phrase, “I can’t go on your adventure” was the title of our discord group for many a month after that. That one-shot retains the title of most perplexing PC decisions a GM ever dealt with. If there is a moral to the story here, it’s this: As a GM, you will get players who make strange, completely illogical decisions. Sometimes, you’ll just have to kill them for it.

And that’s it! Three stories of times when players rendered their GM temporarily speechless. In hindsight, it’s easy for a GM to say “damn, I really should have done x or z,” but in the blind panic of the moment, you just have to make your best judgement call. (Aka. let the players taste the consequences of their bad decisions.) When stumped, stall. And when your players throw you a curveball you have no idea what to do with, just remember to go on Reddit and commiserate with your fellow GMs.