I’m a Male in my early 30s and woman I’ve been seeing is in her 40s and we’ve been seeing each other for about 3 months.

I have very little dating experience compared to her, as she’s had FWBs and a couple of long term relationships whereas my longest has been a few months and I’ve had a few hook ups in college.

Deep down, I feel a bit insecure about this, but I don’t let this manifest while dating. I take everything with an open mind, listen and address problems as they come, and avoid drama; the whole shebang. She has a lot more experience in dating than I do and it comes up a lot in conversation (as in, she talks about more about past dates and such) but I feel bad that I don’t have a lot to add from personal experience. That’s the part that gets me, because it was big on her social life so it comes up a lot in conversation, but it wasn’t big for me.

How should I approach this and keep a good healthy mindset on this? Anyone else have this situation? I try not to let this bother me, but I’m trying to keep an open mind.

Thanks for reading.

20 comments
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  2. You can use it as an opportunity to learn 2nd hand, so ask questions you are curious about. I enjoy asking my friends about their dating experiences. I get to find out what it might have been like if I did it myself, and learn more about my friend.

    If it’s making you feel insecure… Is it just you? Or is she bringing them up in a brag-y way?

    If you didn’t spend time doing relationship stuff, you spent it doing other things, so she might feel the same in whatever areas your more experienced in. That’s just how it is. Don’t worry about it.

    (while past experience could be useful, it could also be detrimental. What if she is completely different and dislikes all tricks/habits/moves/gestures you might have learned from hypothetical past experiences?)

    Thus, the main focus by far, should be learning about each other. Not stressing about past experience.

  3. Why do you need to feel insecure? It’s not a competition. The fact that she is picking you after all those experiences is a positive thing.

    When she is sharing about her past experiences, take on a curious perspective and use the information to understand her, her needs and wants better. Glean the lessons to help the two of you build a healthier and stronger relationship.

  4. Why would it bother you that she has more dating experience ? What does that even have to do with you? Why do you see that as a good thing necessarily?

    Is it because you compare yourself to her? Don’t do that. You’ve been on your own journey and have your reasons. We are all at different stages in life.
    Hell I have 8 years of dating experience. That doesn’t make me better or worse than someone with 2 months of dating experience (they would probably be less jaded than me lol) I would just feel lucky for them that they didn’t have to go through so many stupid dates haha. Although I did learn about myself on my journey.

    Dating isn’t a competition. I’ve never even had the thought that someone with less dating experience is lesser worth than me. That’s just.. horrible. Or that it’s a bad thing at all. I wish it was me lol.

    Work on your self esteem there a little. You are just fine and don’t need to prove yourself. Be yourself and it’s all good. Just because someone has a lot of dating experience that doesn’t mean they are better to dating than you. Just means they have more experience. Nothing more.

    So what if you can’t add your dating experience in the conversation? You can probably talk about topics that she can’t!
    She picked you. Believe in that.

    You can still have conversations about her previous dating life and ask questions etc even if you can’t share your experience.
    Although personally I don’t think I would talk all that much about my previous dating experience to a new boyfriend, but that could just be me. But I’m also more in the now and the moment and find that topic irregular except for maybe sharing a few lame/fun dating stories.

    Don’t sweat it. You are fine.

  5. Why does she bring up “past dates and such?” That just seems odd to me. Does she seem bored, wish that your dates modeled her previous experiences, or is she just randomly bringing them up? Focus on building conversation that helps you get to know her.
    If she brings it up like ” oh I went on a date to that see that exact exhibit!” Just say “you seem like a social butterfly and honestly I’d love to hear more about you and what you love/experienced without the dates you went on.” Keep it simple and honest and see how she responds. And see if she is someone you want to continue to connect with.

    As far as experience goes I wouldn’t put so much weight into it because someone could be very experienced dating but have very little emotional maturity/regulation/intelligence.

    Dating doesn’t automatically make you better but it does help you figure out what you like and it does reveal to you areas that maybe you need to work on when involving another person’s energy into your space/life.

  6. I’ve been on the other end of this. I had relationship experience while she did not. We were both in our 30s so I was a bit surprised.

    There’s nothing to be self-conscious about. For me, I viewed it as a positive that there was less risk of relationship baggage.

    However, I eventually learned that the reason why she never had any relationships was because she was a mega Avoidant who was terrified of sharing her feelings and forming an actual human connection with someone. But assuming that doesn’t apply to you, there’s nothing to worry about.

    I think people get too worried about talking about prior relationships. I never really talked about mine, but I was open to sharing what I learned from them, and it was unfortunate that she would tense up and avoid any prying questions, which then made me want to change the subject. Not healthy…just talk like two adults. You’re 3 months in….you two should be letting your guard down a little by now. You’re well past the intro stages.

  7. Maybe try to reframe this scenario in a different context? If she had- say- more job experience in a field you were trying to break into, would you still feel so oddly about it? Or would you view it as a positive thing? Neither of you sprang into existence upon meeting each other, you both have pasts and histories that inform who you’ve become as adults. As long as she’s not bringing up her past in a negative way (comparing you to old dates, fondly wishing she were with a former partner, or so on) there’s nothing wrong with her saying “I’ve had this experience in this context, previously.”

    I have a current FWB m28 that was military and deployed/TDY for most of the first part of his career, so his dating experience is limited. Whereas I 31f have been divorced once, in 3 other years’ long LTR’s, and had a pretty colorful dating life prior to meeting him. He wasn’t very open with me initially about how limited his experience was, and I find him so attractive/ such an obvious catch that I assumed he had an equally if not more so colorful history! Is your gal making the same mistake? I often try to get new partners to open up about this dating history so we can identify what went wrong in the past and to gauge whether or not they’ve healed/ put in the wok on themselves to not bring those problems into our current relationship.

    So there’s a couple of different options/ factors at play. You’re the one in the situation and know best what’s going on- I wish you the best in talking it out and seeing where this leads!

  8. Why are you so bothered about her experience? It’s not a race or a competition it doesn’t matter, it’s not like a job where there’s a hard experience requirement.

    You have a girlfriend now; keep it that way.

  9. Well doh, she’s a woman and she’s older by 10 years, what do you expect? Women usually have a lot more experience than men. You should not give flying f.

    Hang out, have fun, hook up.

  10. I am also seeing someone who has way less experience than me but we are the same age. Quite frankly my ample dating and relationship experience added nothing but trauma, depression and a bunch of other issues for me. Did I enjoy the process? Hell yes. Was the outcome worth it? I’m not sure. Now I am more drawn to guys with less experience = less drama

  11. You say, “Cool story”, and ask about things if you’re curious. If you’re not, then you move on…just like you’d do with any other story she might tell, that you don’t have any experience with.
    Or is there more to this? Is she talking about her past dating a lot, or just sharing stories about things she’s done or places she’s been?

  12. >I feel bad that I don’t have a lot to add from personal experience.

    Maybe she isn’t dating you with the expectation that you’re going to take the lead with lots of experiences?

  13. I’ve dated someone *younger* with more experience, and that’s way worse imo.

    The good news is that this is all just in your own head, and you’ll realise very quickly that it doesn’t matter, like literally it isn’t even noticeable so why would it?

  14. I’ll add that it’s totally okay to feel insecure, as long as you don’t make it her problem. Don’t try to “not feel insecure”, that’s not how processing feelings works. Acknowledge and own it, talk about it with your therapist, friends, and maybe even with her – as in “hey I’m having this problem, I wonder if you’ve dealt with something like this yourself in the past and have any advice for me”. You could even say “hey would you mind toning down the talk about your past dates, nothing wrong with it per se but I’m struggling with some insecurity and I think I’m not yet ready to be hearing so much about it”.

  15. I don’t understand why she is talking about her past dating experience so much. That just strikes me as oddly specific. I understand having a general conversation about it at some point and the fact that past dating experience may come up occasionally but not often. Is she stuck on an ex? Regardless, stop overthinking this. You have dated. You know what to do. Don’t get hung up on the details.

  16. Bro for all her experience she’s exactly where you are except ten years older. Perspective.

  17. I don’t know what to tell you except that I know how you feel. Last spring, I dated a woman that had been married for several years and dated around quite a bit after. I’ve never had an LTR/FWB situation (never sought it in my 20s) and can count the number of people I’ve dated/had sex with on one hand. I felt intimated and insecure too.

  18. It depends how she’s talking about it. If she’s talking about her flings so much in early dating, it would be hard to take her seriously. That’s just annoying. If she eased into the stories and they’ve come out naturally over time, then it’s just a 40 year old that’s speaking about her life. 40-somethings have been around and have stories. I don’t know how you’d expect anything different. Maybe you be more open with her about your feelings in these conversations. You might bond over something. Who knows?

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