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Being a quiet introvert, I have a lot more regrets in the "What if?" category than in reality. Almost all of those involve a girl I either never got to know, or never tried to take to the more than friends level.
As far as actual 'guilt' for something I've done...
I have two major regrets in my life. Each of which can be blamed on my penis, the curmudgeon. The first one involves my first real girlfriend, and in hindsight is definitely the result of immaturity and inexperience. Basically my junior year of high school I started going out w/ J. We had a fairly good relationship, saw everything in pretty much the same way. I enjoyed having her around and she obviously adored me. About seven or eight months into it, things started to get pretty intense. We went to prom together, had a good time. On the way home she told me that she loved me and never wanted anyone else. This more than just freaked me out a little, so I decided to break it off before it got more serious. The problem was that I never really got around to it. Well another couple months went by with me pretty much just ignoring her every time she said those three words. On her birthday, she called me to see when I was coming over. Basically it was a normal conversation until the end when I said “I don't think I'm going to make it, I think we should break up." I hung up the phone, and didn't talk to her for the rest of the school year. When I finally got my head out of my ass and realized that I was an idiot she was dating someone else, who she eventually married.
My second regret is much simpler to tell. I basically slept with one of my best friends on again/off again girl friend/fiancé. It caused a lot of friction in the friendship for a while but he forgave me, married a different girl, and she is no longer around.
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"Two roads diverged in a wood, and I-
I took the one less traveled by,
And that has made all the difference." - Robert Frost
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