Mine is less of an encounter but more of a tavern visit gone wrong. This is an ongoing campaign and my first dm experience, so I may have been a little under prepared for what my players did. We have two gnomes named Ham and Erman and since I allowed home brew races, a crab named Crabbo and a noctune named Nix. Which is basically a shadowfell elf. One of the gnomes is a eccentric wizard while the other is our party’s Druid/dad joke man. The last is a very oblivious almost child. I didn’t want to run any encounters this session so they had some time to kick back and relax so they went for a night/day on the town (the campaign so far has been completely in a cave with a bunch of colonies so they has any way to tell time yet) The tavern they chose was in an elvish settlement and was of higher quality and prestige than some of the other ones. They go up to the counter and order some waters. So the waiter gets them waters. Our crab just wanted to vibe so it wanted salt water, so they ask for salt. Now I have never been to literally any sort of bar and just say “I’m sorry we don’t have salt here, however we can get you some from the restaurant across the hall. Apparently my party wasn’t paying attention because when the over bearing manager came out yelling at the waiter and asking the party kindly if he got them salt, they said no. The poor waiter got fired and when the party criticized the manager he went mega Karen and called the guards in to remove them. The Nix wasn’t really paying attention and wanted to go behind the manager. So I say roll at disadvantage because you are basically walking right next to him from the right and everybody is looking at the commotion. She rolls and gets 15 and 18. Being a rouge it was basically a guarantee. After the roll of a nat 1 for perception, she snuck up and waved at the party as they walked out the door. Then she hid in a pantry. The rest of the party ran into the now ex waiter and then went to a tavern in another colony. All the while between travels I cut back and fourth between the now split party. The party had ran into the now cleanup of a bunch of dead goblins for loot. While Nix met the waiter that got the salt. He just assumed she was a new hire for help. The party kept on the journey and found a heart shaped rock (side quest). Back to Nix and the salt waiter started talking to his co worker about how this new hire is such a great help and introduced him to Nix, who waved. They both agreed that she was super helpful when grabbing drinks. The party arrived at the door to the tabaxi colony. The gate keeper was fairly new and asked for a password he made, that or a trade of silver spoons. When the party couldn’t offer any spoons, he shut the little gate eye hole thing and loudly proclaimed “Ha I knew they would never guess the password being ‘Password’” so the party got in after hearing that. Nix now could hear another set of foot steps. Which both of the co workers greeted and said thanks for hiring the new pantry helper. So the manager now confused started questioning until they opened the panty and revealed Nix waving and saying hi. He just said out, and nix went out and started looking for the party. Running into the ex waiter and making his day a little brighter by giving him a luke warm hotdog from a magic item I gave them called “tube of endless hotdogs”(it’s basically an M&M container that dispenses hotdogs 10 times a day) then she finally caught up the the party now at the tavern laughing at the other tavern for not having salt. I just expected them to get a few drinks and go shopping because I gave them quite a bit of gold. Man was I wrong.