I know I'm not the only one here who's had a date or relationship that went sour. So, naturally being as curious as I am, I'm interested to know what was the worst break-up/date/relationship that someone's had. My worst break-up was when I went out on a date with this girl in my freshman year in high school and the next week she had her sister tell me she didn't want to go out with me anymore. My worst relationship was probably my first official girlfriend that I dated. She had sexual orientation issues, :-\ , and sometimes a few rough patches with her father. It ended with her breaking up with me because after 3 months of dating she decided there was no chemistry.