Biggest is definitely messing everything up with the girl who is/was quite possibly the love of my life. The way we met and started seeing each other was like some shit out of a movie. We truly were great together. Similar interests, sense of humor, could just tell what the other was thinking. We clicked, but my dick started doing the thinking eventually and, as usual, that was when things went south. I've never downplayed me being the one that ruined our relationship. I was a stupid teenager who thought he was hot shit. I started messing around with someone else. I didn't realize then that I already had what I wanted.

We kept in touch for years after that, both of us seeing the wrong people and each doing our individual shares of different and sometimes foolish things, but still had some level of care for one an other. I mean, she chatted with me online well into the late hours of the night when I was in the hospital after I had some serious surgery for a broken foot. Not my friends that I saw almost daily at the time, not my family, her...who I rarely saw in person anymore.

Then a year later we stopped speaking to each other. Heard from her a few years back, had a short conversation. I could still feel there was something there, or it may have been hopeful thinking.

Anyway, I still think about her all the time and wish she could really know how much I still care and how proud of her and her accomplishments I am. But biggest regret is losing that relationship. I've had plenty other relationships since, but none of them have come close to what this was. And I feel like if I hadn't been a fool we'd still be together now.

Sorry to get long winded and depressing.

TL;DR Screwed up relationship with awesome girl.