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I'm one of those people like your friend... I've had, in the 18 years since I lost my virginity (at 16... I'm 34 now for those of you who wonder about those kinds of things), sexual partners numbering either in the high 3 digits, possibly into the low 4 digits. (Somewhere between 900 and 1000 sexual partners).
Yes, that's a LOT. Yes, I was extremely promiscuous. Yes, those partners were both male and female. And yes, many of those were in multiple partner at once situations. And yes, I had issues. Namely, low self esteem that I thought I was bolstering by repeated sexual encounters. Fleeting intimacy to validate my self worth. I had a few relationships during that time, but they all ended badly, sabotaged by my full set of Louis Vuitton luggage that I was toting around, lol.
The thing is, even after I did a lot of work on my self esteem and self worth... I'm actually a very well adjusted woman these days... and kicking a crystal meth addiction (part of that self worth work was done while I was dealing with my addiction... You spend a lot of time in introspection while you're DTing from a drug addiction), I still chose to live my life in a sexually free sort of way... By that time, it was a habit that I'd developed, and honestly, I liked the freedom that sex-without-relationship afforded me. *shrugs* Its not something that most women choose, but it suited me.
As a woman, my sexual choices were fairly unusual. Most women would rather not have to deal with the damage that such choices make to her reputation and to her future relationships. I'm going to tell you that I'd accepted the fact that I would probably never get married... I'm not one to hide my past, even though I don't broadcast every detail, it has a habit of coming up to remind me that its there... And, especially in a smallish city like where I live, word gets around. There's really no such thing as anonymity or discretion. Things have a way of getting around.
I was lucky. I've known my husband for nearly 20 years. He knew me during the worst of my low points, and he doesn't care... He thinks that my past is part of what made me who I am today, and he really loves that person... I like her, too, and we've been happily married for almost 10 years. He was one of those people with little experience... I'm only his second partner, and was only his third sexual experience. But he doesn't feel like he's missed out on anything, and neither do I.
All I can say to you and your friend... He's got to find his own way. The one thing I can suggest is that rather than dog him about his sexual largesse, you can encourage him to be safe, and to get tested regularly for diseases. That way there's one less thing for him to regret (if indeed he does regret his choices. I don't.) if and when he does find "the" girl.
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“When facism comes to America it will be wrapped in the flag and carrying a cross.”
~Sinclair Lewis
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