My first time I played DnD
The character I played was an elven rogue who was a notorius prankster who was raised by a dragon and was obsessed with their culture. Her father the Dragon gave her a magic crate (like an infinite space box, like hermione’s purse) filled with a bunch of minorly enchanted items. Aria (the elf) decided that she would use these items to become the best pranker in the world (cue evil laughter). Since it was my first time playing, it was just me and the DM with his character, a demonic warrior looking for his master.
Extra context: we are fighting a blue dragon. I’m dying, he’s still ok on health.
Me: okay I’m gonna grab an item from my box
Dm: what are you looking for?
Me: a ring of healing? Idk something to heal me
DM’s little bro(not playing, just watching): Is a ring of healing an engagement ring?
Me: …if you want it to?
DM: (evil snicker) okay roll a d20
Me: shit, 5
DM: So you pull out a ring of healing but before you can use the enchantment, the dragon notices the ring and thinks you’re about to propose.
Me: shit NO Aria may love dragons but NO
DM: roll charisma
Me: *nat20* WHAT
DM: Congrats, you’re now engaged to a dragon.