This happened when I was in college. Names have been changed to protect the (semi-)innocent . . .
The guys at Alpha Beta had a bit of a reputation for being the bad boys on campus. One (Tom) lived on my hall freshman year and I had a class with two others (one a sophomore- Mike and one a junior- Kevin). I joked around with them all semester and had bit of a crush on all three- moreso Mike and (especially) Kevin.
Walking back form class one day with Mike and Kevin, Mike pulled me aside and asked me if I’d like to be his date to their winter semi-formal. It was cute seeing him shyly ask me and I gladly accepted. I love dressing up and was looking forward to that Saturday night. I wore my little black dress and Mike looked very nice in his suit as we went out to dinner before the band and bar at the fraternity house. Two other guys I had met once or twice before and their dates went to dinner with us. I was having a very good time and was even able to get served wine at dinner without anyone asking if I was 21. I kind of resolved with myself that if Mike made a move, I would hook up with him to one extent or another that night.