So I was DMing what was supposed to be a one shot for my friend and this guy she wanted to introduce to the game. She already had a level 1 Rogue rolled up, so all we needed was a character for her friend. Of course he picks a rogue too. So as I'm writing up a campaign in my head while helping him make his character, I decide on doing a bandit themed one shot. So they have this little gnome guy and a tall alluring half elf who come to join the black rock bandits. The chief gives them an 'initiation' mission to earn their place in the band, something simple for a couple fresh blood pickpockets. They just had to head over to the nearby fishing village, steal a magical artifact that's in possession of the town mage, easy peasy. Here's where it gets good. They decide to create a distraction by having the Half Elf throw a bag of sand into the water, pretending it's a child, and scream for help. It was supposed to attract the guards attention while the gnome snuck around. The dice rolls had other plans. One guard shows up, asking what happened. She tells him a kid fell in the lake. He jumps in to save the kid, forgetting he's wearing heavy armor. My friend is now literally in tears thinking she just killed a guard. Meanwhile I'm rolling to see if he can manage to come up for air and take his armor off underwater. She starts freaking out like 'what if he had a wife??' He comes up for air and yells 'Barbara!!!' She cries harder. 'Does he have kids?' Comes up for air again. 'Roland Jr!!!' She's on the floor. Now her partner gives her the sign that he's acquired the target and the Half Elf is forced to run away in tears, leaving the guard to die.
Turns out the guy loved D&D so much he wanted to play again, so next time we got together, I got another one of my friends to join the campaign. This session starts out at the bandit camp and the chief introduces the pair of rogues to their new partner. My friend introduces his character as Roland, the fighter. An ex town guard who lost his job after jumping in the river to save a sack of sand, letting the artifact the town mage used to keep peace with the merfolk that lived in the lake get stolen, got left by his wife and son for being worthless, jobless, and penniless, and was forced to become a bandit to survive.
You shoulda seen the look on the Half elf's face.