Ever regret not sleeping around more before meeting your current partner?

15 comments

1. Talk to him. It can mean lots of different things. It could be that he’s comfortable telling you this thing and doesn’t see it as a big deal. Like regret carries a different meaning. It could be he’s hinting that he wants to break up/be in open relationship etc.

   With that though, I think if someone doesn’t have a lot of experience sexually, it’s normal to wonder or think about it. It doesn’t necessarily mean you are not satisfied with sex or relationship.

2. I’m pretty vanilla when it comes to sex so I personally never understood this romanticization of having all kinds of sexual experiences or sleeping around a lot in your younger years or whatever. My opinion is that if you’re a mature person who is genuinely happy with your partner or whatever relationship situation you’re in, you are not preoccupied by “what if’s” and FOMO. Besides, what does he think sleeping around will accomplish for him? It’s purely a selfish thing for him. That said, you should talk to him about your feelings and get clarity on why he brings it up.

3. I’ve had fleeting thoughts like your boyfriend (I’ve been in a relationship for almost 4 years now and he’s my first everything). But at the end of the day, it’s really down to a grass is greener mindset. For me, I too had a fear I was missing out and all that jazz. But when I really thought about it more, I witnessed tons of women my age, some even my own friends, struggling with hookups and telling me over and over that it leaves one so empty and hollow. It really made me step back and re-evaluate what was going on in my head

   I was simply getting caught up in the unknown and the thought of throwing away my relationship for a few hookups made me feel icky (I also am someone who wants a connection to have sex so I already know I’d be turned off from hookup culture). I realize that I truly have something beautiful. Like you, my boyfriend wants nothing more than to please me before he even thinks about himself. He treats me with such kindness, respect, and admiration and I wouldn’t trade what we have for the world

   But I know I’m not your boyfriend and I don’t know if he thinks these things. If I were in your shoes, I’d probably sit my boyfriend down and explain how those statements make me feel upset and ask if that is something he wants to pursue. And if it is, it may be best to consider the possibility of ending things. I hope it doesn’t come to that point but you don’t deserve to be with someone who is unsure about you. I know when I was at my low point with these thoughts, I didn’t deserve my boyfriend and we had a conversation about it. It was a much needed conversation and I don’t think about these things anymore.

   Definitely bring it up and use “I” statements instead of trying to accuse him of things. It’ll lead into a much healthier conversation. I truly hope all goes well cause aside from this, it sounds like you’re pretty happy and I hope he has the sense to realize that he’s got a good thing. Best of luck

4. A lot of people who haven’t experienced a lot will say that stuff when they’re not content with their current relationship honestly.. Might just be their own insecurity in the relationship too.

   I’ve asked my current partner if they regret not doing that and they said no because they don’t need it or desire it.

5. Dumbest thing ever. I slept around. So what. Imagine you have a soul mate. How much time would you like to spend with them? How much time would like to lose so you can sleep around. Also what if just what if, if you sleeping around at that specific time means you would never be with your soul mate. Because you know they were ready to settle down while you weren’t ready to settle down. You will find another partner but not your soul mate. For whatever reason people assume that life magically works out. You will go sleep around and then magically find the right person. That’s why people settle. Cause guess that right person, right fit may just have moved on or got taken away while you sleep around. If he has regrets then he doesn’t know your value.

6. I don’t have that much experience but imo sex is always better with the person you love, are crazy into, and who feels your pleasure is equal to theirs. (Which as a woman with one night stands really isn’t a given).

   If I had only had sex with one person ever, maybe I would’ve cared by now… then again that would’ve been with my ex boyfriend and we had a great sexlife so honestly I never felt that I was missing something there either.

7. I get that people can sometimes wonder about what they could be missing, but it seems pretty tactless to tell that to your partner.

   > my current partner makes sure he pleases me before he gets off. I am perfectly content with just having sex with him. Is this something I should be worried about?

   I mean, do you make an effort to make sure he is satisfied sexually? Have you asked him if there are things he would like to try/do differently? If you are concerned he might want to experience different things, I would suggest trying to make that happen within your relationship in a way that you are comfortable with. Discuss it with him, and be proactive.

8. There’s two things going on here. The first is how he’s feeling. I’m married and in my 30s. I only had sex with one person before my wife. Sometimes, I have idle thought about what it might have been like to sleep with more people, or have different sexual experiences. I’m perfectly happy with my current sex life, but as you get older it’s natural to wonder about roads not taken, in every facet of life. What if I had picked a different major in college? What if I had moved to a different city? What if I had done X instead of Y? So in that sense, having *idle thoughts* is normal and expected.

   The second thing, and the problem, is that he is expressing this to you at all, and framing it as a *regret*. I would never tell my wife I wonder what it would be like if we hadn’t started dating, and I certainly don’t view that choice as a regret *at all*. The fact that your boyfriend is telling you that is a pretty big red flag in my opinion. He’s either working himself up to asking you to open the relationship, laying the ground work for future infidelity, or giving you a soft heads up about the upcoming breakup.

   EDIT: I think it’s worth asking, though, what is your current sex life really like? You said that he is good to you. Are you good to him? Has he expressed a desire to spice things up, have sex more often, etc.?

9. Um no. I never felt that way.

10. OP,

    A word to your bf…. I am someone who met my now husband when I was 20 and he had just turned 24. He slept with lots of different people before me and I….did not. We’ve been together ten years now. And have had several children. And you know what? I have never felt like I was missing out. I’ve asked him if he misses the sex he had with other people(I know, a brave and stupid question). He said absolutely not, because the sex we have together is the best he’s ever had. Me, too, technically lol. And you know why? Because we trust each other. Because we build each other up so we both feel comfortable suggesting AND trying new things. I can honestly say that our sex life is better now than when we met or before we had kids. Because sex with someone you really love is like wine… it goes great with artisanal cheese. Wait, no, it gets better with age.

    I would talk to him and see what he actually hopes to get out of bringing that up yo you. Because he may only want to vent a bit (though I still think that’s a bad move to do to your partner because they’ll never unhear those words) or if he actually wants to do something about it so he’s not missing out anymore. In that case, well, I would say the relationship is over…

11. I thought I regretted it, so we broke up and I slept around a lot.. It’s overrated.

12. I (m31) sometimes do. And the weirdest part is that I had a bit of casual sex when I was younger and single, and I didnt even like it. I have been with my fiancee for 5 years now, and the sex we have is mindblowing. So I figure its a few different things for me.

    First is basicly just the allure of the unknown. Did I miss out? Are there things out there that I dont know about? Intelectually, I know im not missing anything at all. Its kinda like the call of the void I guess. I know there is nothing there, but my brain just goes “yeah, but what if?”

    Second is probably that I had less sexual partners than my fiancee. It sometimes makes me feel insecure, in the “there is no way im the best out of these guys” way. It feels like if my number of partners was higher, I would be on more of an even footing with her, and it would make these feelings easier to digest. I know it doesnt really make sense, but there it is. The feeling of envy also creeps in sometimes, like “well she did all this, and I didnt get to do it!”, but thats even more dumb than the other reasons. I didnt even like sleeping with casual partners when I did it, so why do I feel envious for not doint it? I have no idea.

    In the end, its a me problem. When feelings like this come around, i simply work trough them like an adult instead of wallowing in them or throwing it in her face. Rationally I know these are just feelings steaming from my own issues and insecurities and fears. But since feelings arent always rational, I still get them.

    I dont think these kinds of feelings are anything unusual as well. I have a feeling like a lot of people get them, and they simply let them pass.

13. All. The. Time.

    It’s natural for us as humans to have desire. If anything, I think it’s counterproductive to believe that it just goes away because you’re in a relationship or you get married.

    I agreed to be with my wife though. I gave her a promise that I would work it out until the very end, or at least until it was no longer healthy for either of us to be in the relationship. But to think we shouldn’t be allowed the thoughts about what might’ve been is honestly immature. There are billions of women out there. It’s normal for me to wonder what those experiences could’ve been like. What I could’ve learned. What loss I could’ve had that would make me stronger.

14. I know a whole lot of men who deeply regret leaving partners they loved for the opportunity to sleep around.

15. Nah, if anything I wish I had less.