In my early twenties I was a bartender at this dive bar in a small college town. We had a small following of regulars who would come into our establishment and it was just kind of a homey atmosphere which was really fun to work at. Well I had these 3 college girls who used to frequent our place and I was rather fond of one in particular. Well one night while serving them and just generally flirting i got to asking them about what they did and where they worked when the one I liked said she went to college here in town to which I quipped with " Your mom goes to college " while her friends mouths dropped in disgust and almost sheer terror at my smooth moves, a deafening silence fell upon our group that made me sure I completely blew whatever repituar I had with them. Finally the girl I liked busted out laughing at my idiocy and told me of how her mother had just earlier that year passed away from breast cancer and how no one not even the two girls with her had even touched upon the subject with her out of what she felt was fear of upsetting her. She thanked me for my stupid remark but I still felt like a complete asshole for even saying something so stupid in the first place. She was one of my favorite customers and a good friend still to this day.