So I've started playing a game of D&D with an animator on youtube I watch. He originally asked me to DM, but took it up for himself because he's never done it before and wanted to try. I decided to roll with Carver Spellmeyer, the arrogant wizard, and we have, in our party, Dragg the horny bard, Wilneas the snobby noble cleric, and <insert name> the dragonborn barbarian ((he has yet to show up for a session)). we've been doing this on roll20 since we're all over the place, and its my first time actually using it properly, so its been quite the experience. We're playing 5e, so its nothing too broken. But apparently, my talk of how good I can be playing (such as tell him about my previous ordeals as Cliff Whitefang the dwarf thrower and so on) he decided to add on a bit of difficulty.
So we started the game with a very awkward conversation between me, Dragg and Wilneas while the barbarian sleeps, which involved them talking about how my familiar just defeated a fish that the DM said was an epic battle, but because me and the bard weren't looking, and the cleric was below deck (he came up because he heard the fish battle) we talked up a bit, and then the cleric starts calling us commoners already.
I tell the bard where I'm going and then proceed to, as my character would do, go down the road to the next town. The cleric follows me because he doesn't want to travel alone and the bard is following me because he thinks I'm his friend. I proceeded to question why they were following me the whole time, and while that happened, we ran into a group of mercenaries, called Los Gayapos Payosos, who were convinced that the bard was named Wally and that he was wanted. Despite telling them that Dragg was not the man he was looking for, I cast Charm Person on the leader and actually managed to convince him then that he wasn't Wally, pretty much skipping the first encounter due to how adamant he was (going as far as to rebuke our remark of saying he wasn't wally by saying "That's what Wally WOULD have said!" and then threatening me and the cleric. Due to the DM's disappointment, he hinted we will be seeing them again)
We make it to town, and my character has to get a key from the bartender. While I'm waiting for him to not be busy, the cleric goes to try and talk to a crazy old man and the bard tries to talk to the seductive woman in the corner. She proceeds to insult his manhood, which causes him to talk to the only other woman in the place, and I'm watching this all take place laughing.
I explain to the bartender that I need the key that he has in order to continue my quest to find my teacher, and that I've been followed by the "two jesters: the snob and the fool" and immediately, the cleric hears me and comes over angrily, attempts to intimidate me by saying "Excuse me, but was there something you wanted to tell me, you uncultured swine?" and gets a 17 on the roll and I roll a 21 as my own save, which caused me to turn around to him, look him dead in the eye and say "I apologize. I've been followed by two JESTERS today, so you can tell my mood is not at its best", which causes him to go COMPLETELY flustered and flash his signet ring and say he's nobility. I then tell him I was a wizard trained by perhaps one of the best wizards in all the land and that his sign of nobility holds no meaning to me. He gets more and more flustered at that and he tells me to hold my tongue and, because he is a half elf, I am trying SO HARD to not drop the racist remarks since not many people like half-elves by calling him a half-breed, so instead, I say to him "What would a High and Mighty snob such as yourself do to me, break a fingernail?" and he just loses it, causing him to draw his weapon and the barkeep breaking up the fight by giving us a discount of drinks. We both order some wine and I roast him again for drinking it right from the bottle when I drink from a glass by saying "sophisticated as always". I also at this point ask for that key and he goes off to get it.
So Wilneas gets drunk and passes out downing the whole bottle and the bard proceeds to talk to the lady, who tells him about a local goblin problem and that her friend has went missing and if he's dead, she wants something to remember him by. So the bard agrees without hesitation and asks me to come along, with the promise of getting paid. I tell him that now I have my key, I have no real reason to stay here, but if I'm getting paid, I have no reason to disagree. The barkeep overhears this and comes up and tells us that it was funny I should mention the goblins because they stole my key that morning. Carver just looks at the bartender with a sharp look of disapproval and facepalms as he realizes that NOW it has become his problem.
Bard wakes up the cleric, I find out he's a lightweight and I steal his coinpurse and give it to the bartender for safekeeping when he agrees to join us and passes out again after I give him more booze... And buy ourselves three rooms at his expense.
Next morning and one hangover later (and giving the cleric his money back), we set off to the goblins, and we start our first real encounter off smoothly: the cleric tries to stealth into the room and rolls a 2, causing all four goblins to turn and attack him. Before he even gets a turn, the cleric is dropped to 0 by the four goblins. The bard kills one and I have to keep the cleric alive, so I can't attack the cluster of goblins with burning hands effectively, so I cast sleep and knock out two of the three goblins (one of which was trying to sound an alarm). The last goblin attacks me and ruins my nice robes (as the DM put it) and then I kill him using magic missile and almost kill another goblin. By now, the cleric has failed two death saves and has one more save. We literally cheered when it came up 16, because that means he didn't die yet and we ended the encounter. I proceed to try and medicine check him, but everything is stacked against us I see as me and the bard failed our stabilize checks. The DM was nice enough to say that we get him back up afterwards, because we did a "what if" roll and found out that the cleric would have died if he was given another roll.
We proceed down to another corridor and hear a goblin in a room where he's grumbling angrily to himself and the cleric, again, tries to sneak in and falls flat on his face as he fumbles. The goblin in the room just turns and looks at him and ignores him, cleaning more skulls. I start talking to him and he's convinced, in his feeling of worthlessness as a goblin, I convince him to get a better job, and the cleric takes it upon himself to hire the goblin to carry his stuff, to which the goblin agrees.
We go into the next room, which is the final room, and everyone fails miserably except me again, with me taking out two goblins on my own and the bard killing another after fumbling a stealth roll and announcing he was coming in by slamming the door open. I get dropped to 1hp again, ruining my clothing more (I told my DM that the next cantrip I'm getting is mending) and the cleric heals me. The goblin buddy we made, kills one of the goblins himself before I cast burning hands, and then he proceeds to kill the goblin leader and stab him over and over for bullying him and treating him like garbage.
So in the end, I find my key, we bury the girl's friend, find his ring and some gems, about 100 silver and a magical fragile scimitar.
We head back to the tavern and Dragg immediately goes over to the woman who insulted him earlier and says "WHO'S THE MAN NOW!? I DEALT WITH THE GOBLINS!" and I use minor illusion to spell out the words NOT THIS GUY over his head, which caused the woman to give me a smile and a giggle, and then gives the bard another shot, even though he completely ignores her after that.
So, overall, probably the worst "first encounter" I've ever had to fix, got a goblin buddy who's apparently going to become a first level goblin fighter (since he did most of the work in the second encounter with me) as what the DM is thinking, and a very enjoyable game overall. Its great to finally be in a game without having a min maxer or someone mad at me for my backstory