I felt kind of depressed after slaughtering the entirety of Paradise Falls so that I could rescue the children and get into Lamplight. I realized that this was a proper town, with a hotel and shops and everything, and real NPCs, and I had just killed everyone in it. I couldn't even spare the cook--he whipped a kitchen knife on me. So that was kind of a downer, even if they were slavers.
After completing the Tenpenny Towers quest, however, I had absolutely no problem with shotgunning that bigoted ass Roy off the balcony of his stupid penthouse. He had it coming.
As for funny, I was on the quest to save the residents of Big Town from the mutants. On the way back, Red kept getting killed. I decided to give her some armor, but all I had was Raider Painspike, which is very spiky, and also renders a female wearer virtually topless barring a few bits of scrap metal and strategically placed duct tape. I figured, what the hell, it's just until we get back to the town. Unfortunately, I misjudged the distance back to the town, and Red and the other guy ran in and stopped being followers before I could take the armor back. So now, whenever I visit Big Town, mild-mannered, peaceful Red, occupation town doctor, is wearing an outfit that makes her look like a gothic hobo stripper. Whoops.
I found the interior of Vault 87, with the mutated FEV test subjects, fucking terrifying. It was a combination of the darkness, claustrophobia, ominous music, and horrifically screwed up corpses in every room...I really expected them to get up and try to bite me.
The Dunwich building was creepy too. I need Point Lookout so that it makes more sense.
And the weirdest thing--there was an area of downtown DC filled with Super Mutants and Centaurs and a booming voice screaming ominous and insane stuff all over the place. I never found out where it came from. (I'm sure someone knows; please DON'T tell me as I'd prefer to find it for myself.)
I could go on all day. So many experiences, such a huge and spontaneous game...love it.