What are your funniest D&D Stories (Dungeon Masters only)?

I accidentally made bunny rabbits terrifying. I don't know how, but all I did was just throw a bunny rabbit in the scene I was describing. My players were ridiculously cautious of it. They decided to take a 3 day diversion along the peak of the valley than walk through the grassland middle where the rabbit was. From then I started throwing bunny rabbits randomly into my descriptions. Everytime they saw a rabbit they acted like they've just seen 3 pixies. It was very funny. In the battle with the BBEG I threw a rabbit into the combat. Just to see what my players would do. The rabbit just ran around while my barbarian and paladin decided to chase it around (missing) trying to kill it. The BBEG took out the bard and the rogue. The party died all because my players thought the rabbit was the BBEG all along. I really enjoyed GM-ing that campaign.

i just started my very first campaign and already have a great story.

im a goblin barbarian in my party, the rest are an earth genasi monk, goliath cleric, human ranger, human/snake person rogue? and elf bard.

it's session 2 right now and our cleric player is not present, so we say she is super high. our goal is to get to a city that is sponsoring us as champions, but we had to pass through the rival city that is basically communist cuba. we've been here a day already and have met the leader of the city, he was sweet talking the whole party as he treated us to a lavish meal and sent us off the next day with an objective. after finishing that we come back to his palace and he reveals he knows we are the champions of the other city, and says he would like us to be his champions instead. we accept and he orders us to burn his old champions alive, which we do. but after that we realize that we have to swear a magical vow (think unbreakable vow from harry potter) that means we must follow his orders. now we have second thoughts and say no to his offer, but we already killed his original champions. so bad guy says that he will let us go alive if the monk cuts off his arm. there were way too many gaurds there and we were level one, so we took that deal and he kicked us out, after keeping the earth genasi arm. let me reiterate, that was THE SECOND SESSION that somebody lost an arm. we start marching into the haunted forest we need to get through to arrive at our sponsor city, but its a 2 week walk. after a small event of a merchant just attacked by goblins we get ready to sleep for the night. we set up shifts so that we dont get killed in our sleep, but after my goblin goes to sleep, i get a nat 1 on a wisdom save and get horrible nightmares of my entire family ripping me limb from limb and killing me repeatedly. i wake up to see a monster that can only really be described as a spider centaur, top half hag with gaping mouth and bottom half spider. it was dementor sucking me or whatever and left when i woke up. we ended that session with a traumatized goblin and a monk with a missing arm. 3rd session starts and this time the rogue and bard players arent there, but the cleric is. so we have to drag 2 bodies through the forest while being haunted by that monster. we get ambushed by goblins and are saved by giant wooden spikes flying out of the trees to impale them. what greets us afterwards happens to be your friendly neighborhood MANTICORE who tells us to give him a reason not to kill us for coming into his forest. at this point, the party isnt even scared, we're more just tired and done with the situation, so we calmly ask if there is something we can do for it to let us go. we managed to escape the manticore with the deal that we have to kill the monster that traumatized the goblin, and bring back some treasure from it that is more valuable than us. so we start marching through the forest again and now it starts raining. we find shelter in a cave to escape the flooding and lightning, but there are dead bodies scattered around in the cave. among the dead bodies is one that has no head, but no visible wounds. after we get a short rest a bear decides to waltz into the cave, with some muffled screaming coming from its stomach. we kill the bear and out comes the immortal hobgoblin Cosmo('s head). we reattach the head to the body and he says he'll help us get out of the forest. cosmo has been alive for 600 years against his will so he encourages us to kill ourselves whenever we feel like its too hard, because "nothing really matters" afterall. next day we follow a glowing blue spirit looking fox because why tf not at this point, and arrive at a chapel, a graveyard, and a mirror. after sending cosmo in to check it out it seems like its ok so we all approach. party ranger looks through the mirror, sees a life a luxury and starts getting pulled in. monk tries to pull him out but cant, so goblin barbarian shatters the mirror while ranger is almost fully in. after that a bunch of shadowy hands start reaching out and crawl out of the mirror. DM asks us to roll initiative and session 3 ends there.

I have never played before and I’m gonna be the dm for a group I’m putting together and man respect to any dm who learns and remembers all this there is a stupid amount of knowledge to absorb to even run a basic campaign

I put my wife on a murder mystery and she ends up in a graveyard. I have a single zombie come at her. She tries to persuade the zombie that she's not an enemy and should be allies, she's a Rogue. I have her roll persuasion check with disadvantage and she rolls a double Nat20. So now she has an enchanted dagger that lets her summon her zombie ally.

This guy is actually swagger souls but he’s just speaking normally

If this was more than just D&D, I would tell some stories, but we're kind of limited with it just being one game, so I can't tell the story of how a Dynamaxed Alcremie sat on one of the player characters in a Pokemon Tabletop adventure I ran.

So one of my party members ended up having to go afk, so he let me control his character until he got back. The party was in the middle of a fight with a giant shark and the character I was controlling was a wizard and on shore, so after seeing that the paladin in my party wanted to punch the shark for whatever reason, I used chill touch and slapped the shark right in front of him. Shortly after on his turn he got a critical hit with unarmed strike and killed it. Funniest moment that I've ever DM'd for.

Back in HS I was running a dungeon delving campaign and my younger brother asked if a friend of his who had been playing AD&D for years could play and, not seeing an issue, I said yes. That was where the headaches all started. This guy seemed to want to play all the stereotypes at once, lone wolf, Mary Sue, glory hound, and treasure whore, the whole shebang. To try to get his way he was an Uber rules lawyer. To top it all off his character was a Dollar General Raistlin from Dragonlance.

Now I have always been more a follower of the Rule of Cool. I like a good story and I want to keep it rolling as much as possible to help with the immersion but this guy was making that dang near impossible. After defeating a decently powerful foe for their level only to have the wizard bully and verbally abuse the party to get to keep the magic thing-a-MA-Bob (Hey, this was over 30 years ago) it was clear that everyone, myself included, had had enough of this guy. Instead of kicking him out though I revamped a trap just a few rooms over. So they enter and there is an altar with cryptic, spider writing on it. The wizard loudly declared that this was a puzzle for the learned and proceeded to try to read the script. I had him roll to see if he could read it and he failed. He then launched into some crazy story about how, since it wasn't a critical failure that because of some special rule he once read about in a book we didn't have on hand that he had actually had passed. I had anticipated this and told him, "Okay, your character is confident that the inscription says something about something called the Wish of Eggoflan" and gives instructions on how to activate the altar. The wizard smugly walks up to the altar and puts his hands on it and loudly invokes the Wish of Eggoflan.

At this point Several of the other players start gathering their things to leave but I ask them to wait just a moment. In my deepest DM voice I announced that the torches lining the walls grow dim and suddenly go out before flaring back to life. Where the wizard once stood is now a large Belgian waffle...with a face. The wizard's player starts to complain but I silence him and tell everyone else that all they hear from the waffle is a series of loud and long belches. That's right, he wasn't turned into a Belgian waffle, he was turned into a Belching waffle! Needless to say the wizard was pissed and the other players were practically wetting themselves laughing. Once they calmed down I then asked for perception checks. They all passed and I said that they noticed 2 things. First, there had appeared on the altar a large plate and a very large bottle of maple syrup. The second thing was they heard a voicecoming from behind them in the distance saying, "Eggoflan, hungry. Want waffles!" Shortly after that a large minotaur resplendent in his loin cloth and napkin under his chin combo sporting a large knife and fork entered the room and yelled, "Leggo my eggo!" At this point The players, who had already picked up the wizard, started running for the door. What ensued was a crazy maze race where the rest of the party discovered how to restore the wizard and ultimately humility was learned and that problem player actually was able to relax and integrate into the group and many more adventures were had with all of us enjoying the game. :)

Players Perspective; As I was playing DND with my friends (one of them has a sister who is playing with us) We were resting in this coastal Slavic town, where we got to sit down and eat. I decided to conspire with my friends sister and we eventually came up with a funny moment for the campaign. After the group ate dinner and rested up at a hotel, I decided to seduce my friends sister and rolled a nat 20, resulting in me laying with my friends sister. Once we got out of the hotel and we were meeting up for another mission I yelled to my friend across the street in game and shouted “Aye Thorn, I fucked your sister!”

Which resulted in the entire table dying in laughter

I have 2 stories
1. the very first session I ever ran, the cleric picked up the paladin and threw him threw a door because it was locked. The cleric rolled a nat 20. And then it happened again a couple sessions later.
2. after a few failed attempts to bribe a dragon, the wizard decided to punch a wall and pretend to die. I asked for a deception check and then had the dragon roll insight against it. The dragon rolled a nat 1, and thought the wizard was dead. The wizard then rolled a nat 20 to slink out of the cave, on the ground the whole time.

One time I was dming a group of people that collectively agreed that they were going to be super evil. They found a random child in the woods that was lost, the only reason they didn’t kill her was because they wanted to go back to the town and kill her in front of her mom. They fell into a cultist trap on the way back to town and had to solve puzzles and get clues to get out. They ended up forgetting about the kid. At the end of the temple there was a statue to bhaal killing a lonesome kid with one magically locked door. They killed the kid (which thought they would do) and escaped later the mom appeared, the group ended up TAKING HER TO THE TEMPLE AND SACRIFICING HER!

Ayo i first now realized we are both Rippers in name xd

I recently ran my DND group (I play a barbarian/cleric) through a one-shot. They were going through a tournament in another plane of existence. One of the challenges was to get past a door locked with a cryptex lock with a 15 character password. If a player hit the door it boosted their INT by 2 until they moved away from the door. This effect stacked. Since attacking a door is not something that people normally do I gave it a magic mouth that would insult the player that failed to guess the code.

The goblin rogue has been the main one trying to pick/guess at the code. Fast forward a several insults and no one has hit the door. So I have the door say something in goblin (no one else speaks goblin) and forced the goblin to make a CHA save, DC 12. He fails and goes into a blind rage. He spends the next few rounds attacking the door in a blind rage. Since I decided to let the buff stack he finally snaps out of it with a 34 INT score. He blinks a couple of times and solves the code in 2 seconds. As they are leaving the arena the buff wears off and he slides back down to 12 INT.

Poor little guy saw the top of the mountain only to slide back down to the bottom.

This is funny to me, but is a mixed bag.
I can have a bit of a odd sense of humor and when I was 16 I tried to DM for my first and only time.
I was beginning to get burned out with DND due to the GM being GM vs PC and the games were becoming less fun and more just frustrating.
So I wanted to try and run my own humorous campaign as a breather from the more stressful campaign. Let everyone laugh and unwind.
I spent three weeks setting everything up. Serious moments, intense combat, and outrageously funny events. Then the game began. The party was to meet their new contract dealer inside of the only pub in town called "The Dragon Foreskin" When they went inside the dim lighting casted everything in a deep shadow. They followed their instructions and in the corner sat a woman with her face vailed and snakes watching them from her head. Bla bla McGuffin in temple to retrieve. They rise to leave and then suddenly the whole room goes black and the chatter falls silent. Music begins to play and a bright intense light snaps on highlighting a large stage where a giant female Red Dragon is at the center wearing a cheerleader outfit and starts to dance around a large pole....
And the players noped out of the game. Stating they wanted something more serious.

So there I was, being a DM. My and sister were playing, and zombies came up from the ground. My sister‘s first reaction was “Are they Ash Zombies?!” And I said roll for that. They weren’t Ash Zombies, but my sister tried every single time she attacked the zombies to try and slice across their eyes to blind it. When she finally succeeded, the other Zombies were dead, by the time that happened. It kept succeeding on its constitution save, and my sister kept trying to kill it, with her only having ONE hit point. Eventually, they killed it. After THIRTY MINUTES of us playing. Right after the battle, they immediately said, “Is there any fruit in the trees next to us?” I said yes, there were apples. When they ate it, there were worms. My brother happily ate the apples, no problem.

I LOVE the idea of a fantasy insurance corporation in Faerun which is then incentivized to protect its assets

Hoping for the playable owlbears one day

Headcanon that after the mintaur ''phased'' through the wall, there was a big minotaur shaped hole in said wall.

We have a half eagle paladin and the city was under a food shortage he wanted a bagle for 1 copper 100 copper is 1 gold he had 4 gold the baker said 3 copper so he made him afrad of him baker runs off a 16yr old soldir enters so my freind dumps out his bag of eyes and pecks at them scaring him in the end we ended up in a dungon

Just recently, I ran a one shot campaign as a first time DM. We were unable to play our regular sessions since one of our members had been busy with life, and I wanted to learn to DM and use Roll20. I set up a short story where cursed wolves were attacking a village and the party was hired to solve the problem. Get to the end and they encounter the Werewolf that was causing all these problems, and I made it attack my brother's Paladin, who has an AC of 18 (16 from chainmail, +2 from shield), and when I made the werewolf attack, he rolled just low enough to match his AC, but to make things more interesting, I had it rip off the shield from my brother, to change the way he fights. He said, "OH no you don't! I roll to take it back!"
He rolled a Nat 20 strength check. I let him roll a d4 bludgeoning damage, describing how he yoinked the shield back and smacked it in the face with it.

Love the video, definitely needed the laugh.

So my friend hits the check to find a tripwire

She just walks over and tells nobody else


She also rerolled dice sometimes (new player, she stopped) one time it rolled into a nat 1

I say that RNGesus got mad

Hehehehehhehe

They were fighting a group, and since luck actually hates me, the group either doesn’t attack, or miss.

One of the players noted, “They need to get better aim.”

Hehehehe

I proceeded to get multiple nat 20s and absolutely demolished them.

the party had to take out a small lookout fort. one of my members has a real life ability to mess up words and likes playing 6' dwarves...im not joking😂 so as the party was planning, the 6' dwarf kept saying we need a tree bucket. this went on for about 5 min until the barbarian leader yells out ...WHAT THE HELL IS A TREE BUCKET!? so the 6' dwarf shows the picture in the weapons and armor book that read...Trebuchet😂😂😂😂

You have such a infectious laugh

I was a new DM to a group of new players, so we were running Lost Mines as a learning experience for us all. One of us couldn't make it to the session, so over the course if a couple weeks, I sat down and did a short solo session (with mixed results on difficulty, as you can imagine) with them separately to explain in a story sense how they are gaining their new powers as they reach level 3. The Halfling Ranger is subclassing into Gloomstalker, with Goblins as his prefered prey. He gets kidnapped by a Cult of Fanatic Goblins who are going to sacrifice him to their god. Well he escapes and steals one of their cloaks as a disguise. I've planned this session around stealth, since thats what the Ranger really likes. Its not meant to be combat heavy since if he's caught, he'd be quickly overpowered by the goblins. Well, he's sneaking through the caves, assassinating goblins rather successfully one by one. He reaches a room with a couple goblins and a pit in the center holding Wargs. He wants to get past them, but doesn't want to let them live, either. So he goes back to the previous room and grabs the body of a previously killed goblin and brings it to the warg pits with it slung over his shoulder. And then, through a series of successful deception checks, straight up Weekend at Bernies this goblins corpse right up to them explaining how drunk he is. The goblins tell him to get him out of here, and with one more roll on athletics, manages to throw the corpse at both goblins, knocking all of them into the warg pits. And the scent of blood from the corpse sends the wargs into a feeding frenzy. Needless to say, he was very proud of himself, and I really didn't see it coming. XD


Tl:dr

Halfling Rogue uses Weekend at Bernies tactics to escape and kill goblin kidnappers.

It may not be that funny but here’s mine

So I do a homebrew campaign where my party hunts down an assassin, I planned for them to have their second encounter with him at the end of a dungeon where they thought to meet the leader of a guild that would help them. Instead they needed their entire session to choose their horses because they rolled so bad on their animal handling. After that they forgot about the dungeon and somehow their whole goal and are now halfway through to build their own dwarve tavern

Once, one of my players was playing a bard and he was spamming Visious mockery and coming up with new and unusual insults for everything they fought.

My cleric used command friend on a pterodactyl in the middle of a boss fight with a king with a ton of dinosaurs

The Hime Lich. cleric.

So a mage/cleric prestige class, likely true necromancer with an ice aspect.

Minotaur assassin... i cant

I run a star wars game for my 9yo son, and he was on Nar Shadda watching a sporting event in a stadium. After the event, people were cheering, fireworks were lit, and to add to the celebration my son's character threw 2 thermal detonators high into the air (as makeshift fireworks). I asked if he was sure, something i do liberally for him as he is only 9, and he said yes. I ruled that they exploded high enough that nobody was injured, but that it caused immediate panic, and several people had seen him throw them. Cue a chase and escape offworld, and being wanted for potential terrorism on the moon. We havent been back, yet.

my funniest story as a dm
my first and current and only campain im running so far started off as "hunt of haldraxis" module from questonomicon, that after its completion i expanded upon (it was mostly me testing the waters), the incident happened in the first two sessions, its nothing too special but funny to see my player being clueless
the party of 3, one of them being arakocra sorcerrer which the funny thing is about. the party was meant to slay a red dragon, the bird sorcerrer was draconic bloodline sorcerrer, aswel of the red dragon, at the first encounter with the dragon (there were 3 of them) she casted a firbolt.... against red dragon... thats immune against fire damage... whooops, however the funnier thing was, that on the second sesion with second encounter with the dragon, she wanted to do the same thing, again, and she would, if not the other party member that yelled "NO DONT DO THIS HES IMMUNE" with the most worried tone possible, after he realised whats going on

it was priceless

Graham Drive

2168 Maxie Highway

DM here!
My group were tasked with exploring a ship that had run aground and had to find certain artefacts. One was on the lowest deck searching around in the dark doing their darndest to avoid a ghoul that was wandering around.
Meanwhile on the 2nd deck the other friend decided to open a locked chest, with a large axe, VERY LOUDLY, alerting the ghoul to HER position. The friend on the lowest deck decided to jump onto the back of the ghoul to save the oblivious friend on the second deck, while yelling "HELLLP, I CAN'T HOLD ON! GET YO BUTT DOWNHERE NOW!"
They did somehow manage to kill the ghoul.
Plus with various failed attacking attempts and athletics checks throughout the adventure there were several face planting moments and unconscious body dragging. It was hilarious.

In a 3.5 game I had a player use reflective disguise to go to a tavern that they knew was a front for an assassins guild. The spell makes you look like a generic person of the same species and gender as the people looking at you. He figured if he looked just like them, he could get some information out of them related to their current task.

What the party didn't know is that the guild was a DOPPELGANGER assassins guild. All these doppelgangers in their assumed disguises watch what appears to them to be a doppelganger in natural form saunter in off the street and start chatting to them... as if that's an absolutely normal thing for a doppelganger to do, just walk around the city in its natural form.

For those not paying attention: IT IS NOT!

The party is actually above level 10 so actually well known in town, so it wasn't hard for the guild to send representatives to the party's base of operations... and they basically beat him there because he thought he'd be tricksy and take a winding route to lose any tails. They didn't tail him. They just walked to his house and waited for him to get back. Then they had a long talk with the party about what they expected going forward unless the party wanted an assassins guild gunning for them.

When the party later discovered the fact that the assassins guild were a bunch of doppelgangers I had to pause and remind them, "Oh, so now that you've discovered this... I'd just like to ask if anyone remembers the time that (character's name) walked into their business using reflective disguise? What do you think he looked like to them?"

That incident was brought up for the rest of the campaign whenever that character came up with ideas for plans. "Remember how well your plan for investigating the doppelgangers went?"

I had a great seduction moment. I played a female halfling rogue with max charisma and I used it all the time. We ran into a powerful wizard and the party was spent, low on health, out of items and ready to give up rather than die. I went in first, unbuttoned my blouse and rolled a seduction check. I passed, the wizard came to kiss me and as I embraced him, I stuck a dagger in his belly and our barbarian came up from behind and lopped his head off. The DM was pissed because he wanted an epic battle, but we took care of business.

I wasn't the DM here, no this happened to me.
we had just started playing Lost Mines, it was the very first session and we reached the Bugbear hideout, cue my Cleric deciding to sneak around the Back way and surprise attack.
DM calls for an acrobatics roll Nat 20, no issue. I didn't see the Bug Bear Chief standing on the Ledge right next to me. DM rolls his 2 attacks and BOTH crit. I take 30+ hp damage and am instantly killed.
We were level 1, and I had 13 hp.
I should add that this was the very first combat roll of the campaign.

Edit: Forgot to add an intro. This was the first long campaign I dm for and oh what a game it was:
Second session, I had my party help break out a local prince, our warlock (Asher) with a demon patron, after learning he was going to be sacrificed to said patreon if our paladin (Mika, full name Mika Might (god I love this party)) was proven not to be the love of his life and sacrificed instead. There was also Sophine our chaotic funny death cleric who was the head maid and assistent of our warlock.
All three of them were in Asher's room and had the plan to escape at night through the window Sophine left open for them.
DM(me): You hear footsteps approaching, and a shuffleing of metal plates.
Ash: Crap, I forgot my dad sends guards to patrol the hals at night.
Mika: Wh- How, you both said this plan was safe, I knew I should have left the second I heard of this. Alright listen here, he should have no problem with me being here but I don't think he will buy that you (points to Soph) were just standing here past your working hours, so, here's the plan.
DM: As you say that you hear a knock on the door.
Guard: Hello your highness, are you alright in there?
Mika: ... Ok, he's closer than I expected, uhh, thoughts?
Sophine(ooc): I take off my skirt (she specified that she had shorts under, can't remember how) and open the door.
DM: ... Uhh, ok? The guard is about to say something but quickly stops after seeing you, confused.
Guard: Oh... Miss Andrews, what are you doing here... With these two?
Soph: Hello oficer, well we were just about to finish up, could you give us a moment please.
DM: Oh, Roll me a-
Soph(ooc): No, no, give me time.
DM: ... Ok?????
Guard: Uh, I'm afraid I can't leave you here unsupervised. Plus your.... Lack of lower covering does raise concern.
Soph(grins irl): Hmm, I mean I guess we could make room for one more... But you will have to be a bottom.
DM: ... Roll... For it?... Give me a deception, with disadvantage cause wth.
Mika(ooc, irl next to Soph): ... Pffffffffff aw man.
NAT 20 has entered the chat
NAT 20 has left the chat
...
NAT 20 HAS ENTERED THE CHAT... AGAIN
...
At this moment the whole table just erupts, Ash leans over takes a photo (now lost :() of the dice trying to stop shaking.
A bit later, after a break.
DM(cry laughing): I... No, no, I mean... The guard's eyes widen for a moment and he starts turning red, taken off guard by your response. He stutters through an excuse before slamming the door, a bit more ruddely than intended. You hear hurried footsteps heading back to the direction they came from.
Ash(ooc): Come on man I really wanted to smash an NPC in one of your games. (Inside joke)
Soph: Aw man next time I'm rolling persuasion.

Long story short: Cleric scared off guard by proposing a four way.
Man, I really miss that campaign.

What if, for that last story, pulling the finger was the somatic component for Thunderwave, which they cast in a winter town at the foot of a mountain, setting off an avalanche?
Story told by witnesses: "He asked some kid to pulled his finger and half the mountain fell down! That kid never went anywhere near that mage again!"

Okay shorter one (I have tons tho so ill share more) my players were exploring a castle and trying to not get caught by the guards. Long story short, the guards started to catch on and one screamed "COME OUT" and one of the rangers just yelled back "IM GAY." They got caught and thrown out of the castle, but that line blindsided me.

My players were inside an abandoned tavern with a back room they needed to get something out of before leaving. So the door out was locked. One rogue wanted to pick the lock. I said “ok but it’s gonna be contested.” Multiple of them freaked out thinking the door was actually a mimic! Well the rogue rolled a nat 20 while the door rolled a nat 1 so they got it open but there was only pitch blackness outside even to those with dark vision. I eventually guided them to the back room where they fought some rats and acquired the time they needed for the campaign but their faces when they got contested by a door was hilarious! 😂

So basically my party was in a forest where I wanted them to fight a dinosaur. They tamed it (Nat 20). They moved to the next City, where one of them was arrested (backstory stuff). They put their Dinosaur in a pen, and then went to break the arrested guy out. They made it, but they were seen by the guards und needed to run. They went for an airship, stole it, and escaped towards their next destination. The Place they wanted to go to was already in sight, when one of my players screamed out: "We forgot Hörnchen (name of the dinosaur)!" So they flew all the way back to the City they had barely escaped, got the dinosaur and RAN. They never went back to that place.

I was playing with my friends when they where screwing around but when we where fighting aunt sally was against us well we killed her and won the fight but on a diffrent game there's a aunt buttress and what the description for that was: Aunt hurts use is that you and we all started dieing of lafter😂😂😂😂😂😂

That dm that keeps insisting he’s bad. From only the things here is the opposite of bad.

Couple stories here as a DM, and 1 from when wife was DMing.

1. My party had just finished out of the abyss and moved into homebrew territory. In essence, the goddess of time (ex-wifes character) was trying to destroy the world and they were figuring out how all the plot points were connected. They eventually join a caravan from Luskan to head to find an old stronghold, and in the process, get ambushed by some improved bandits. They, being level 16, wipe the floor with them and proceed to try and figure out how the bandits appeared. My wife, who had been playing for 2 months, figures it out first and teleports into what is effectively the barracks of a castle with 50-70 bandits all staring at her while her party is miles away trying to figure out what happened. My first thought as the DM, was crap im going to kill a player. Instead wife looks around, realizes its an enclosed room, and casts fire wall completely filling this room with a fire and the screams of 95% of the bandits. She simply covered her face with a wet cloth and waited for her party. Fast forward a few turns, and the monk figures out the trick and joins the druid right as the druid hears bandits yelling to create an opening for arrows. The monk does fancy monk sht and runs across the walls (prince of persia style and a nat 20 +16 acrobatics) and proceeds to start pummeling the crap out of the bandits at the doorway. Rest of party joins and has to not lose their stomach from the smell of burning flesh as the bandits, absolutely terrified, turn the battle of the stronghold (which i had planned to go very differently) into the bandits fighting a losing guerilla style of fighting.

2. During the time I DM'd adventurers league (organized play) my players were going through storm kings thunder. The go to the fire giant stronghold and have successfully managed to sneak through on the upper ramparts. They want to get over to the king and the barbarian (26 str) decides to roll to see if he can throw the tiny half elf warrior. This man is known for rolling an average of 6-7 nat 1's a session, and a nat20 once a month. This time he rolled a 20 to throw her with a +12 to athletics and yeet her across the room. The elf fighter was a great sword wielder battle master and proceeded to roll a nat 20 for acrobatics followed by a nat 20 for athletics. Having met the checks, i narrated it as follows.
"As Ulthag the mighty barbarian yeets the tiny sword demon elf warrior, its like the stars align and the throw is perfect. Her muscles and reflexes in perfect sync as she is yeeted and begins slicing like crazy."
The elf warrior received advantage on all attacks, action surged, and with the giant slayer greatsword +haste cut the fire giant king down in 1 round earning her the name of the blender. Once he was dead, she turned around dead panned to all of the fire giants and while wiping the blood from her face, asked who was next? Needless to say, that boss battle ended through roleplay as the giants were terrified of the blender.

3. My players had tagged up with an old player from a previous canonnical campaign to travel on his boat to kill a shadow dragon. The paladin/wizard decided he wanted to spend his time using catapult on the supply crates to launch at the dragon. Most missed, but after the 8th round of him doing this, he finally hit. The entire time, players were telling him to draw dawnbringer and use it but he didnt want to and finally used catapult, on dawnbringer whcih hit the dragon. Killed the dragon, but dawnbringer was lost tonthe depths.

4. Party after storm kings thunder are in the process of traveling to Luskan via ship. In the process, the party is ambushed by a dragon turtle. The silver dragon paladin of bahamut had beennsuffering with whether dark decisions could be good and immediately approached the dragon turtle and bribed the dragon turtle with 10k gold if hed go away and eat the next ship that came along (there was a ship coming he was aware of that was part of his backstory). In a show of creative priblem solving, this paladin avoided two boss fights. The dragon turtle killed the partys pursuers and they got to Luskan 2 days ahead of schedule.

Lastly, the first time my wife DM'd, we were doing a seaon 0 one shot. I was playing a circle of spores tortle druid named Doneshello (cranky old man who prefers the wilderness) and my good friend was playing a ranger named Kuntry who was like an adopted son to Don. We are trying to get information from a mage, and don, being don, decides to make.some herbal tea. However, i roll a nat 1 on perception and dont see Kuntry sneak down and put laxatives into the tea. I bring the tea up and after a few minutes, the mage says we need to leave as she has business to attend to. The party, not sure whats going on, walk outside which is when i finally fail my con save (nat 1). Don, being a druid, goes and points his butt down an alley before pulling into his shell, and falling on his belly letting it all fly down the alleyway. This was in the middle of a market square causing all kinds of chaos and my wife needed 20 minutes to recompise herself after i said "Don wants to go to the nearest alleyway, point his but into the alley, retreat into his shell and sht all over the alleyway like a bad bad turtle.

Hope others appreciate these stories 😂