So our forever DM was attempting to start a D&D 5E campaign with our already established group of friends, we had met at an fan-made-non-official Elder Scrolls 1-shot game where I was the DM, we stayed in touch and became friends after that, so we all were expecting good chemestry and lots of fun, even though I hadn't played D&D for 18 years (!) (seriously, my last game was in 2000 and this happened about 2018), one of our players was pretty experienced but not a senior, and two of the team were newbies to both D&D and roleplaying (at least as a table top game), so only the forever DM had both experience and was not rusty.
So there we were, a Giff cleric (by the way that's when this dude started his exotic character choices and never ever he chose a simple elf or human after that XD), an Elf warlock, a Tabaxi monk, a Tiefling bard and me, a half-elf rogue.
Everybody had created super complete backstories with royal bloodlines, demonic pacts, god's favor and whatnot. I was an orphan who grew on the streets of a city with no home. I really wanted to focus on roleplaying my character to make its backstory grow with the campaign, I wasn't sure if I would get to make it while helping less experienced folk in the party, and needing help to get used to 5E myself. I was affraid the characters of the newbies were too over-complicated or hard to play for first-timers, the only experienced player other than me never played a 5E bard before and they changed a lot and he wouldn't know how to fully use it, and also that the DM had in mind a very human-based society as a background world and our characters would have trouble even entering the town but the DM was very open and his homebrew world was very diverse, the DM seemed to know how to induct new players to the game, and the other experienced player helped me a lot with the "new" 5E stuff, we were up for a good start.
So after a few tips to the newbies on how to roleplay by the DM, and some help to me about the changes form 3E to 5E (yeah, told ya, I was rusty), we start the campaign in a tabern, classic start, the local authorities entered the saloon and said out loud that they were stretched thin with an ongoing war and held a reward for a "minor" job of aprehending a local thug that was comitting simple crimes in the city, like pickpocketing citizens, smuggling goods, that sort of stuff and then they proceed to mention the handsome reward. Some of our characters already knew each other and were drinking toghether, the rest just accepted the job and that's how our party met and got our first quest.
So we discuss the plans, I let them know even though I grew up in the streets (I was obviously a rogue) it was in another town and I didn't know the local hive of scum and villany, and had no clue who or where the thug could be, so we decide it would be good to start right there at the tabern, asking (or bribing) some clues out the barmaids. Of course the bard does his bard thing and tries to ask the barmaid, there goes the first dice roll of the evening: nat 20 holy Tiamat. The barmaid not only tells the bard everything she knows, but she falls in love with the bard, forgiving the lodging and food money to him and the party, and gives us a starting lead: she had seen some smuglers in a corner of the city.
Off we go to chase our smuglerS (thanks to the barmaid now we know it's not only a thug but a group of thugs at least), the lead took us to some alley where we were told there was some door with a dude always waiting at the door and allowing shady people pass, but the door led to no house of the block, at least no house the maid knew, which led us to believe that might be a passage to a secret hideout in the sewers or something like that.
We get there like… all toghether, not hiding and in plain daylight (first facepalm of the game, let's count them) , so the doorman thug sees us and immediately flees, of course.
"What do you do?" says the DM. I was leaving room for the newbies to interact, not wanting to be the spotlight all the time but they had no clue, so as I was about to suggest we follow up stealthily form a distance and see where he leads they all pursue shouting the guy to get back, second facepalm and I have no option but to follow the group of maniacs (it was funny actually). So we follow the doorman to another alley where he attempts to escape by jumping a fence, then our bard decides to cast Vicious Mockery on him "ok roll" says the DM. Nat 20 again holly Lolth. Rolls for damage: basically ee fried the doorman's brain. The DM's expression said it all, he was not expecting the doorman to just die there, but unfortunately he did. Now we had nobody to interrogate, third facepalm and counting. By the way people around town saw a party including a Hippo-man, a demon and a cat lady running around chasing some dude and they started to gossip, we had to do something before they saw us with a dead body. The sorcerer (who was good in alignement) decides it's a great idea to try and reduce the body to ashes to get rid of the evidence, so she casts a firespell I don't quite remember burning the flesh but not quite incinerating it completely. Another facepalm, at this point I lost count. The way we were derrailing a simple starter quest was actually hilarious and the DM seemed to be enjoying it. The DM warns the sorcerer that she'll need to rethink her alignement or stick to it if she didn't want to be punished in the future, which made the already shy player go even shier and avoid performing any action for the rest of the evening.
We still had a body to hide, now scorched, with no aliby whatsoever on why we killed and disfigured him. People started circulated into the alley so I tell the DM "I tie the body with my rope, jump to the other side of the fence and pull it to that side". DM makes me roll for acrobatics: success. I cover the body with my cape and shout the party to get something to cover the move the body out until we figure what to do. They get some sort of wooden cart and meet me in the other side of the alley where I was waiting with the scorched body, the party decides it's a good idea to ask for help of the barmaid, now that she had feelings for the bard, another facepalm on knowing the difference between falling for someone and willing to hide a body for them, but I roll with it so they make their own experience.
We get to the tabern and the Giff tells barmaid to please help, SHOWING THE DEAD BODY THEN AND THERE. At this point I'm not even counting the facepalms anymore and the DM is really amused at the bizarreness of the situation. Of course she panicks and flees shouting "guards, help!". I sigh deeply both in real life and in character, take out my rope, and proceed to chase and tie her to a chair inside the tabern's kitchen (it was not busy hours luckily and the kitchen was empty). The bard proceeds to try and calm the maid down with his charm and fails horribly, she anyway agrees to help after the explanation on the condition we don't ever return to her tavern when this all was over. She helps us hide the dead body in her basement and warns us she would alert the guards if we didn't solve the case or removed the body in 24 hs. Ok we had a day to fix everything, this time I take the wheel and propose my fellow murder hobos to at least try and interrogate our suspects before killing them next time. They all agree. We come up with the plan of waiting in the alley and try to pass as the doorman, they all agree the one resembling more like a human would be me, so I disguise as the doorman (success roll on disguise). I won't bore you with the details, it was a pretty standard adventure after that, we managed to access the door leading to the underground and disbanded a gang that was using orphans to smugle and steal in the city, we were handsomely rewarded and in the following sessions we were able to help the sorcerer to dare to rolepĺay again, and help the Tabaxi and Giff to roleplay at all as they only threw dice on the fight scenes during the first sessions, the bard learned how to use a 5E bard, and I really got a taste for playing half-elf rogues after that, and not thinking about spell slots, complicated background stories or race feats, just roleplaying and fun.