During one of our sessions, our party (a male half-orc barbarian [Me], a female human cleric [my youngest brother], a male dragonborn warlock [my younger brother], and a female tiefling rogue [my cousin's younger sister]) came across a travelling band of mercs along the road. Our mission was to infiltrate their base and (hopefully) relay information back to our quest-giver. Sadly, our noobness (Yes, that's a word now.) and indecisiveness led to us being stopped by said band of mercs. We were consequently questioned and, in our panic, could not respond properly. Worse, the DM (my cousin) said there about 50 of them and we were a few steps away from TPK if we didn't do anything sensible.
It was then that the cleric stepped up. Or should I say, my brother. All he did was convince the band to allow us passage. This sounds easy, but the DM did not roll for persuasion checks the whole time. It was basically my brother applying all of his time playing games like Dragon Age and Mass Effect and taking to heart the various ways dialogue plays out in said games to pull it off. In the end, we ended up becoming part of the group without a scratch all thanks to my brother's IRL diplomatic skills.
Since this post didn't include anything funny (as posts in this group usually do), the first thing I did when we arrived was pick a fight with one of the orc leaders. I lost an arm and some of my teeth in the process. In retaliation, I killed him and took over his part of the army. But they didn't like me and I had to fight 20 other guys to prove my worth. I won them all with just one arm.