Most Helpful Guy
I've dumped two women twice in my life. I regret dumping and hurting first one; we dated from 1984 to 1986, 26 months. We lost our virginity to each other. She was nice and loving, but, she seemed to drift away from me and not want to be with me (although, I later learned that I was mistaken in some sense). At that same time, I was getting contact from other women and one in particular is a girl I had a crush on since the first grade. So, not to cheat on my girlfriend, I formally broke up with her because of what I thought was going on in our relationship and the thought of possibly having a new one with my crush since childhood. That didn't really happen (although we did make out), but I never did get back with that girl although we have remained friends.
The second girl I dumped I have no regrets whatsoever. It was 1989 and it was a LDR. She was a rebound relationship. In December 1988, I was in a friends with benefits situation with a roommate but didn't realize it because I loved her. She was a nympho and I was her fuck toy for three weeks until she found a hotter guy. (Long story there.) Anyway, I was on the rebound. One night in March 1989, a buddy from Texas was at our bar but he had his friend (a girl) from Texas with him. She obviously was very hot for me. Being on the rebound and a bit bummed, I soaked up the attention. So, we became a couple. She wasn't very good looking either but I was in my prime. Still, I was a nice guy. In July 1989, she lived with me that month. The sex was OK but it seemed obvious to me that she was very conservative and had a script in life - get married, have babies. I saw myself as an actor in a play - a wallet and a sperm bank to give her her 2.5 tax deductions and wood-paneled station wagon. I was ready to be dead yet since I was still in grad school. But the final straw was when she said that I wanted it (sex) too much. I was thinking "WTF? I am 26 and in an LDR! I need sex... and you're not good looking either!" I pulled away after that knowing that I was not going to marry this girl and would have to terminate the relationship. That last week was tough. I tried to remain friends the rest of 1989, but it wasn't going to happen. She promptly got a new boyfriend and was married within 2 years with kids within another 2 years. Her life is better and my life was definitely better. I have no regrets about what I did because it was the best for both of us.
A year later, I would then meet the love of my life who dumped me 24 years ago... *sigh*0