Let's hear about it. When did you really blow it? And did you come out better or worse in the end? Here's mine: I was in medical school 20 years ago. I was single. Never had much of a social life, particularly in those years. Not a huge amount of sex either. There was a young woman named Teri in my class. Young in spirit but actually in her late 30's which made her a little unusual for being in med school. She was absolutely beautiful with a radiant smile and a body that could stop traffic. We became very good friends and flirted quite a bit. One night she invited me over to watch a movie. It seems that her VCR (remember those?) was in her bedroom. So we watched the movie, me being completely oblivious to why this woman had really invited me over to watch a movie in her bed.......... So eventually Captain Obvious gets the clue and we have a passionate evening of lovemaking. The first time was the best 20 seconds of my life; luckily as a younger man I could reload quickly and it went swimmingly thereafter. She was experienced in the bedroom and clearly had a lot more to teach me than we could get to in just one evening. So she snuggles in to get ready for bed (undoubtedly to be followed by hot morning sex and breakfast) and I then get up and announce that I have to go home. She looks at me incredulously and I tell her that I have to be up early to go on a bike ride the next morning. I am not making this up. Yes, a fucking stupid bike ride with the cycling club. And out I went. I was very lucky that she remained my close friend after that. When I think about my possible role as her boy toy and all I missed out on I shudder. Interesting footnote: As I said we remained very close friends. 6 months later I went on a first date with M, the woman who would later become my wife. We went on a second date and ran into Teri partway through the evening. So I called her the next day and said "So what did you think of M?" and her reply was "I think I'm going to dance at your wedding." And 3 years later, there she was dancing at our wedding.