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Small-Scale Question Sunday for November 2, 2025

Do you have a dumb question that you're kind of embarrassed to ask in the main thread? Is there something you're just not sure about?

This is your opportunity to ask questions. No question too simple or too silly.

Culture war topics are accepted, and proposals for a better intro post are appreciated.

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You're welcome. For what it's worth, I don't think it's a problem of values per se. I suspect (though I can't prove) that many if not most people are wired to want sexual exclusivity (including past exclusivity) with their partner. I've known plenty of people who don't have traditional values around sexuality, but who say they would rather not know about their partner's body count because it will just bother them. That suggests to me that, despite our culture's attempt to brush promiscuity (or even serial monogamy) off as "it's just sex, who cares", many people are in fact deeply wired to care about sex and to not be able to easily shrug the past off as "well, (s)he's with me now so it doesn't matter".

I agree with the advice of both @yofuckreddit and @ThomasdelVasto - this may be something you have to compromise on due to the nature of the society we live in, but not necessarily so because people waiting for marriage do still exist. Just be aware you're making it harder on yourself to find a partner if you make that a dealbreaker. Nothing wrong with that, one simply has to be aware of what they are setting themselves up for.

For some unsolicited advice of my own:

  • Be prepared that even if you figure you're ok with someone with a sexual past, your feelings might change. I didn't start to suffer from retroactive jealousy until my wife and I had been dating for 9 months.
  • If you think you might struggle with this topic, try to resist the temptation to sleep with a woman before getting married. My wife and I were already sleeping together when I started to struggle with her past, at which point there wasn't anything I could reasonably do about it (besides keep struggling) without being a massive hypocrite and the scum of the earth. What was I going to do, break up with my (then) gf because I felt bad because she had sex with other bfs? We were doing that very thing. Nor could I have tried to then find a woman who was a virgin without being a virgin myself (at least, not write being a massive hypocrite and the scum of the earth). I know how strong the temptation is - firsthand. But I wish I hadn't gone down that road.
  • If you pursue a relationship with a woman who has a past, and you start to struggle with feelings of retroactive jealousy, do not talk to her about it. I did this with my wife (while we were still dating, and once briefly after we got married) and all that it accomplished was that I hurt her deeply. Because what could she do? She couldn't change her past, after all, nor does she have a magic wand to wave to make my brain stop being hung up on this topic. Instead she rather bitterly remarked that she wished I had a gf before her whom I had slept with, that way it wouldn't be a struggle for our relationship. She also lamented that she was going to be a cautionary tale for Christian girls everywhere, that if they had sex with a man they didn't then marry it would ruin their marriage. For my part, all that happened was I got horrible guilt that I get to carry around that I hurt her, and moreover that I continue to have the feelings which hurt her. But I did at least learn to never speak of it again - I would bet dollars to donuts that my wife has no idea that I still struggle with these feelings of jealousy (though thankfully much less often than I used to, probably due to the wonders of habituation).

Regardless, good luck brother. I doubt it'll be easy for you, because it hasn't been for me. I can only hope that some of the advice here (from me but also others) will help to make it a little better. I wish that human psychology wasn't susceptible to this failure mode, but alas it is. I am truly rooting for you though.