What romantic gesture did you feel bad rejecting?

There was a girl in middle school that was really into me, and open about it. She wasnt my type, taller than me (which I'm into but makes me feel insignificant...lol)

She asked me out, I told her I was seeing someone (I wasnt) and that i wanted to just be friends. She insisted on the girls info. At the time, I was frequenting an AOL chatroom that I had friends in, I randomly hit it off with some chick that lived near me in one, and we were both young and stupid, asked her to be my girlfriend and tell the other girl to politely leave me alone. She said yes (wtf?) and did. They actually became ok texting friends, talked a bit apparently, and I actually dated the other girl for over a year.

I still feel bad about my middle school friend though because I use to talk to her on the phone all the time, we'd go out and do stuff like ice skating, etc.. and hung out a lot, but I probably led her on like crazy, and looking back I wish I didnt, but I just wanted to be friends.

/r/AskMen Thread