About 8 months ago at work, i was stuck in an endless "So's your mom" loop. When people would talk to me i would randomly reply "So's your momma", i thought it was funny, other people thought it was funny, it was great.
Sad twist, one of my co-workers mother died, but i couldn't get out of the loop. One day i diverted it into a "So's your........dad?". I felt like a total tard and he must have known what i was gonna say. Also once the Xmas party was around the corner, we had to sign a page saying if we we're going or not, plus put our "Guests" name beside. Well, one of the guys i work with didnt like me all too much, so i thought he might find it funny to put "Gregs Mom" (greg is his name) as my guest. Im sure you see a twist coming up, well i didn't know his mom was in the hospital at the time, so i looked like a total jerk, when all i was doing was trying to make him laugh so maybe he wont hate me oh so much.
So yeah, sometimes if you try to be nice and sociable, you just f**k it up even more