Eleventh level party of Ferrin (half elf wizard/artificer), Sister Serena (aasimar cleric), Xanlar (half elf paladin), and Nu (axolotl shifter druid),  plus NPCs Phillip (human ranger), and Pin the kobold (rogue). 

Fighting the boss we've been pursuing for some time, having stealthily boarded his armored river ship and very unstealthily attacked him.

DM: "That's 30 necrotic damage to you, Serena."
Serena: "Fun fact, Aasimar are resistant to necrotic damage."
DM: "Oh. Bah!"

Nu: "My kids turn!" [Nu refers to summons as their "kids," in this case a swarm of velociraptors]
DM: "Yes, and they are afraid."
Nu: "Six them are."
Serena: "There are ten more!"

Nu: "And I'll play my flute."
*rolls 2-1=1 performance*
Nu: "Uhoh. Oh, I had it backwards."

DM: "Ferrin's turn!"
Serena: "Ferrin's been having such an exciting battle this session."
Ferrin: "He's having the best nap of his life!"

DM: "You are invisible. Pixies cannot see you."
Nu: "But what if I'm screaming?"

Ferrin: "How many rounds do I need to be unconscious for it to count as a short rest?"

DM: "Nu, your turn! What does the giant flying invisible pink octopus do?"
Ferrin: "That's a lot of adjectives."

After a battle that lasted a session and a half with the boss going into a second freaky giant spider-ish abomination phase before fleeing via teleport.

Serena: "I'm screaming angrily at the glowing bastard and the world in general."
Ferrin: "Imagine being conscious and being able to do stuff."

Serena: "I want to search the wreckage for that chest I saw in there."
DM: "Roll Investigation."
*1*
Serena: "Everything's really wet!"

===

Serena: "Wait, you're saying the dwarf went upside down, her skirts flipped down, she turned inside out and became a triton?"
Ferrin: "Not inside out, just upside down."
Serena: "Sure. Because that totally explains it. How does that biology even work?"

===

Serena: "Is that bed a pet mimic?"

===

Nu: "I kick the drunk guy"
*1*
DM: "He hugs you."
Nu: "I do not like this."

===

Pin: "Okay then, if there's nothing to do for me here I'm leaving."
Serena: "Don't get in trouble."
Pin: "Never do!"
Serena: "That's an abject falsehood!"

===

Serena: "Can't you do that with druidcraft?"
Nu: "Why would I have druidcraft?"

===

Pin: "Hold this bag and don't ask questions."
Nu: "As soon as he leaves I squish the bag a bit to make sure there's nothing alive in it."

===

DM: "Serena, he looks straight at you."
Serena: "Do I have to make a saving throw?"
DM: "Yes!"

===

It's explained that we are being sent to retrieve a magic violin from the tomb of a necromancer bard that could control undead with his music.

Ferrin: "So it's the crypt of the necrodancer?"
DM: "I hate you a little."

Druid: "If you do that I'll attack you."

Fighter: "If you attack me I'll eat your faerie dragon."

Druid: "What! You can't eat Peeves!"

Fighter: "Why do you think I've been feeding him all this candy."

Druid: "What?"

Fighter: I've been fattening him up to perfection."

Druid (OOC): "I'd like to, over my short rest, pull one of the bones out of the wyvern, sharpen it to a point, tip it with its own venom, light it on fire, and stab Rogue with it."

Me, the DM: "What the hell?"

Rogue: "Yeah, What the hell?"

Fighter: "Yeah, What he- actually I want to see this go down. Rogue owes me money"

Me and Rogue, at the same time: "What the hell?!"

"Blood may run thicker than water, but gold runs thicker still. Get your butt in here, you got spending to do."

Fun fact, most people that say "blood runs thicker than water" use it to mean the exact opposite of the original meaning. It refers to blood spilled among fellow soldiers who fight alongside each other being more meaningful than the shared water of the same womb that siblings are born from. 

Wizard: "Can I offer you a nice d4 in this trying time?"

Barbarian: "The universe is unraveling, we're fighting a goddess, and the best you can offer is a d4?"

Wizard: "Fine then. Don't take it."

Barbarian: "I didn't say I didn't want it!"

Warlock (to Rogue): "Hey Rogue? I... I need a human skull. For no particular reason."

Rogue: "Only if you agree not to ask."

Warlock: "Fine."

Rogue: *pulls 7 pristine human skulls out of his bag* "Take your pick."

Warlock: "..."

Rogue: "..."

Warlock: "That one will do."

Player 1, having just draw a card from the Deck of Many Fates, offered by a fortune teller, and losing his memory: "What are we doing here again?"

Player 2: "Oh we're robbing this lady."

Fortuneteller: "Wha-" ::Proceeds to get sucker-punched by a bugbear::

This bugbear didn't really think about how that fortuneteller going down might fling the entire Deck of Many Fates out across the room, but hey, the DM said he was having trouble coming up with a plot...

From a series streamers.

"Let it do it's thing. Chaos is a ladder." (said many times in several adventurettes by the same character)

(Lawful Evil Whispers Bard shows manacle connecting his wrist to the Chaotic Good Spirit Bard)

Whispers Bard: "What the HELLS is this about!?"

Spirit Bard: "I think we need to try and build a "trust exercise" after you almost murdered those people back there."

Whispers Bard: (takes out knife) "Give me the key, or else."

Spirit Bard: "I suspect the key is somewhere at the bottom of this mountain."

Whispers Bard: "You MADMAN! I swear I'll kill you, and...!"

Spirit Bard: "Quick question, mate?"

Whispers Bard: "WHAT?!"

Spirit Bard: "Do you know the spell, "Heat Metal"?

Whispers Bard: "...you wouldn't DARE."

Spirit Bard: "Even I don't know what I'm capable of."

Whispers Bard: "You'd burn yourself!"

Spirit Bard: "I'm trusting you that I don't."

Whispers Bard: "I'll cut your hand off!"

Spirit Bard: "Before you get burned, mate?"

Whispers Bard: "I HAVE FIRE RESISTANCE...!"

Spirit Bard: "REE-ZIS-STANCE...such a funny word. Sounds nothing like "immunity". But you do you."

"Those who fight with swords are fools. those who fart-" (Gift of gab) "those who fight with swords are fools. those who fight with bows are cowards. you, my friend, shall be burned by the stake-" (Gift of gab) Are both a fool and a coward."

Barbarian: *crashes through tavern wall* "OOOOH YEAH!"

Bard: "Oh no."

*For context, this is a campaign set in a Roman-esque setting*

Guard 1: "Welcome back, traveler!"

Bard: "Good to be here! Oh, I never asked your names."

Guard 2: "I am Pentus, for I am the fifth child in my family. My compatriot here is Sextus, for he is the sixth in his family. What is your name?"

Bard: "My name's Liv."

Pentus: *starts counting on fingers as his eyes open is horror* "Holy Jupiter...."

This is a moment where I sorely wish I could add also a reaction and not just a like in these forums. I'll do it here, instead.

🤣

(After reading an ancient text about a major villain's origins)
"Now remember, the 13th godshard is Koris, and he's lost his way. He needs to be gay again. Someone needs to seduce Koris, that's all I'm saying."

Joined a one-shot a few days ago. Level three characters, some of the other players were totally new to the game. I was a Tiefling bard. I’ve played a thousand times before- and DMed- but my brain seemed to convince itself that I knew no DND strategies. Here’s how it went.

In the very beginning, we had to get to an island. We first tried using a shoe as a boat, which involved me persuading the merchant to give us a shoe even though we had no money. We acquired the shoe, but didn’t think ahead how all five of us were going to fit into an object that the wizard had cast a simple enlarging spell on. (The shoe only doubled in size.)

After arguing pointlessly for a bit, the cleric finally suggested we just get a boat from a nearby shipyard. The DM was disappointed in us.

Once on the island that had a passageway underground and leading to the under-city, our party went to investigate some crime. We assumed the sewer tunnels we had to go through were booby trapped, but to make sure, the dwarf suggested we send someone ahead to just see what would happen.

Dwarf: Alright, who’s expendable?

Human: Me!

Wizard: What are you, again?

Human: A fighter.

Wizard: Oh yeah, go ahead.

Luckily for the poor human, my common sense kicked in and I suggested the cleric cast Find Traps.

All in all, it was a fun time.

Acolyte: Do not throw that at the shrine! Our goddess will be very upset.

Chaotic neutral Tiefling who’s had his fair share of trauma with gods: Whatever. The gods can go die.

Cleric: Gods are immortal, you moron.

Tiefling: WELL THEN THEY CAN YEET THEMSELVES INTO A DIFFERENT PLANE OF EXISTENCE. SEE IF I CARE. *sets shrine on fire and storms away*

The acolyte started sobbing and tried to douse the fire while the rest of the party slowly backed away.

Dragonborn: Should we go find him?

Cleric: Nah. Give him some time to yeet himself into a different plane of existence. He would be doing everyone a favor.

Aspen: I am not a genocide!

DM: There is a chest at the end of the hallway.

Rouge: Ah yes! Loot!

Cleric: Ah yes, death....

DM: Um, what is [character]'s hair situation?

Player1: She doesn't really pay much attention to her hair.

DM: Most people will notice when their hair starts falling out in clumps.

Player1: Yeah, but she's not really attached to her hair.

Player2: Well, not any more.