What's your biggest sexual regret?

I have this friend. Absolutely. Gorgeous.

We'd known each other for a couple years, but hadn't had much one-on-one time. If we were together it was usually with another friend or a group, so I never really got to know her well. She was beautiful but seemed kind of uninteresting, so I didn't put much thought into asking her out. She was out of my league anyway.

I really enjoyed going out on weekends with her and her roommate. Eventually she invited me to join a bowling team we'd both signed up for. I was going to drop out because it looked like I'd be saddled with randos or no team at all. It wasn't until that bowling league that I really started to notice her though. All of us would shoot the shit, drink beer, and throw balls for a few hours. She was stunning. Sitting in that crummy bowling alley, she was immaculate. Her usual confidence melted away a little as she was learning to bowl.

As time went on, she started making eyes at me. At first I brushed it off. After a few weeks I pieced together that she had been checking me out. The compliments, the looks she gave me. It all just clicked. My chill evaporated at that point. If my roommates had been home when I realized this, stories would have been had. I was ducking ecstatic! Here's this amazing girl- the kind that could land whomever she wanted- and she digs me? I was correct about this, right?

Unfortunately, she had just started dating another guy :/. She was talking with our teammates about him. I, completely unaware, asked who he was, and she said, "Just some guy I'm seeing." They dated for months, but I never heard her call him anything more than that around me, despite the two having a fairly serious relationship.

I visited her while I was on a trip a couple weeks before she broke up with him. I guess that was a mess, but I digress. During that time we had a great time touring her hometown and chatting, but at the end I flew back home. I saw her a few months back, but we live several states away now. She suggested I visit but only casually. I'm too much of a puss to plan that trip because part of me always thinks "Maybe I got this wrong. What if the narrative I've built up in my head doesn't reflect reality, and I just blow it by asking her out."

I'm wise enough not to get too invested in these things at this point, but maybe she'll be the one that got away.

/r/AskReddit Thread