I’m 34, single and looking for someone to settle down with. In my younger days however, I saw a lot of sex workers—I lost my virginity to one (at 24) and used them to build my confidence up until I felt ready for a relationship. My best friend “Sam” is well aware of this, and because he has literally no secrets from her, so is Sam’s wife “Amy.” For the most part I get along fine with Amy—I was the best man at her and Sam’s wedding—but she is a rather extreme feminist who believes that sex work, while maybe okay in theory, is in our current reality exploitative of women and therefore evil. She wouldn’t even let me take Sam to a strip club for his bachelor party—I ended up not doing it because Sam genuinely didn’t want to, but I’m afraid this gave Amy a sense of triumph and power she doesn’t deserve.
I had been seeing a woman for almost four months who I was starting to think was the one, when she abruptly confronted me about my past with sex workers. When I admitted it was true, she dumped me and bad-mouthed me all over social media. Turns out she heard it from Amy, who “thought she had a right to know.” I ended up getting into a huge verbal altercation with Amy when she refused to either apologize for sabotaging my relationship or promise not to sabotage future ones, that ended with Sam ordering me out of their house with the threat of physical violence.
That was about two weeks ago. Sam and I finally just talked again, and we both really want to reconcile, but when I asked him to talk to Amy and ensure that she won’t tell any future girlfriends of mine about this part of my past, he said he can’t control what Amy says or does, and seemed to imply that I was some kind of Neanderthal for thinking a husband should have that kind of control over his wife. I don’t see it as control, just common courtesy and regard for others’ privacy. I have no intention of continuing to patronize sex workers once I’m in a long-term relationship, and don’t think any good could come of my future girlfriend/wife knowing about this.
But I don’t see how I can keep it a secret if I continue to be friends with Sam and Amy. And I really don’t want to drop them, especially Sam. I don’t have a lot of close friends—in fact he’s pretty much it. I love their two little boys to death, and I think their family has been incredibly valuable to me in terms of modeling healthy parent-child relationships, since my own family of origin was anything but. Now though, I keep thinking about how every time I’ve ever asked one of Amy’s friends out, I’ve been rejected, even when we seemed to have great chemistry. I’m paranoid she’s been telling everyone and that her and Sam’s whole social circle sees me as some kind of scum.
So what do I do? Do I need to find a woman who is cool with the fact that I used to see sex workers? That would narrow down an already narrow playing field even further, since I’m no longer looking for a casual fling or a party girl, but a woman with good values who wants a faithful monogamous relationship and motherhood. When and how would you suggest I tell a potential girlfriend this, to keep her from dumping me in disgust like the last one? Or do you have any other suggestions?