Basically the title. These past few weeks I’ve (27F) been dating this really sweet guy (27M).

The only issue so far is I’ve learned he’s never been in a relationship. He’s gone on a few consecutive dates with some women but nothing more than that. I’ve dated a few guys who have never been in a relationship before, and they were very selfish and terrible communicators, so I think that’s why I worry this will become a bigger issue down the road.

Has anyone else dated someone in their late 20’s who had never been in a relationship before? Did it turn out to be a red flag, or did it work out?

In a way, I feel like his relationship Guinea pig which I know sounds bad, but idk I just feel like people grow from each failed relationship they have and learn more about themselves and what they want and don’t want each time. Is it possible to have a good idea of what you want if you haven’t been in a relationship?

Thanks ahead of time.

25 comments
  1. Why ask other people how you should feel?

    And why not just try it with him? Experience taught me that prejudices are shit.

  2. What reasons did he give?

    Busy studying/ working or his former dates were bad women?

    That might give you an idea how he thinks and treats women.

    How are his relationships with his mother and sisters?

  3. I’m sure we all know people that have been in several relationships that can’t communicate for shit.

    It’s an individual thing. Almost works in your favor because maybe you can set him off right with expectations of boundaries, communications, etc

  4. No telling why, maybe you found a diamond in the rough.

    Don’t hold it against him, you will see if he is sponge-worthy soon enough.

    Btw- what does it mean “I am unsure how to feel?” Can you decide how to feel?

  5. Well, geez, I’m 31 and never even been on a date. Guess I’m eternally fucked at this point.

  6. I’m biased, because I’m in a similar situation to the guy you are dating.

    He could be a bad communicator, but he just as well could be a late bloomer. If you really like him, I’d stick around and see what happens. Unless there are mor obvious red flags, I wouldn’t be too concerned. The truth is, a lot of guys just don’t gain their confidence until later in life.

  7. People are individuals. Do you feel every 27 year old woman who has been in a relationship is about the same when it comes to dating and communication skills? Probably not. Might he have those issues? Certainly, but I wouldn’t assume he will have problems he hasn’t displayed. I would also give him a bit of wiggle room to learn. Most people learn a lot from their first relationship and he won’t be used to communicating the way you do in a relationship. That doesn’t mean he will be bad at it once he gets used to it though. Just means this is new.

  8. So whats the big deal? If you like him, and he is good to you, then date him. Sex is overrated.

  9. I heard that a lot at job interviews… great qualifications but not enough work experience 😀
    no but jokes aside… you said he is a nice guy so judge him for that. You said he was shy and had issues with his confidence in the past… so I guess that’s explains it.
    If that’s the only reason for you to second guess then I would say give it a chance. Anyways maybe better than someone who has a lot of relationship experiences but never managed to keep one.

  10. Personally, I don’t see how communication and never being in a relationship are significantly correlated.

    Anyone can get into a relationship quickly, it just takes communication to keep it going

  11. I took a guy’s virginity when he was 25 and after we broke up he stalked me, hung out with my mom, and would take my younger brother to places. I couldn’t get rid of him for awhile.

  12. Hey, 32m here who can sympathize with your guy.

    I didn’t date really at all in college, or until my late 20s. I had a perfect storm of already being an awkward introvert, taking a very intense degree program, and on top of it all I had undiagnosed depression and anxiety. I really did want to be more social and date, but I was too overwhelmed to figure it all out, let alone actually do it.

    It really wasn’t until I finished school, got proper psychiatric help, and generally learned how to actually take care of myself that dating even became a possibility, let alone something I was actually able to make happen.

    I was definitely afraid I was going to be judged pretty negatively based on my lack of experience by women I dated. I’d be willing to bet your guy was/is, too, and if he’s the good guy you think he is, I’m sure he’ll appreciate your understanding. I know I did once I finally had my first relationship as an adult.

    So all that to say, his previous chronic singlehood very well could have a benign explanation. He might be awkward in some of the more intimate parts of the relationship, but again if he’s the good dude you paint him as being, he’ll be so grateful for your patience as he tries to catch up.

    On the other hand, yeah he could have been perpetually single because of being off-putting lol. Any time you meet or date someone new, you’re gonna run the risk of them turning out to be a shitty partner.

    I hope it works out for you two!

  13. My bf (25) had never had a girlfriend until me. He’d had flings, but told me he never wanted to commit. I was a bit concerned and thought this was a red flag.

    We have definitely had communication issues, but he is the best boyfriend I’ve had. He is so genuine, and sweet. My ex had been in a 4 year relationship before me, and he treated me pretty badly. I guess it completely depends on their personality. I now live with my bf, and every step in our relationship, he has been the one to suggest it. He tells me he was just waiting for the right person, and I fully believe it.

  14. You could be his first relationship and sexual partner, if you’re willing to treat him like a person and not the cultural stereotype of a virgin or loner. You say he’s sweet and that his lack of experience is the only issue. If you’re willing to be patient with him regarding some things, you could be an amazing first relationship for him!

    If you keep thinking of him as a “possible red flag” though, do him a favor and leave. He needs someone who looks at him for who he IS, not what he isn’t.

  15. My boyfriend (25) and I (27) got together 4 years ago, he had never dated anyone. I initially thought it would be a problem as well, but he’s honestly the best. We’ve had issues about my body count before but after having a conversation about it it worked out fine. Communication was rough at first but if he’s the right guy and you run into problems, just be honest and tell him what you what. That’s what i did and his communication is top tier now. I don’t think you should let that stop you!

  16. The first relationship teaches important lessons for all future relationships. Do with that what you will.

  17. More like nice, he doesn’t have relationship baggage. Mega win.

    He might have a few untested preconceptions, though. Not that that’s any different than usual.

  18. I was exactly that guy and I would like to think I’m not selfish and a terrible communicator lol (at least my partner would agree)

    There are lots of reasons why guys lack relationship experience, and not always does it relate to personality flaws. For me, it was growing up in a conservative household and focusing on my career/education, so I didn’t really make any effort to date whatsoever until mid-20s. On the other end, there are people who get in and out of relationships on a regular basis, but I wouldn’t say their experience helps them navigate relationships in a particularly healthy way.

    If you like him and think he’s a good guy, I wouldn’t hold lack of relationship experience against him. But, if you project negative preconceived notions about people without relationship experience onto him, then it probably won’t work.

  19. These are the exact posts that make me feel like it isn’t worth trying at this point.

  20. Hey OP,

    I was 31 when I met my current partner. Was not a virgin but had never been in a serious relationship before.

    I’ll admit the first year or so were hard for us both because of me. I was a bad communicator and struggled with some jealousy issues. She worked with me, I started therapy, and it has been bliss since. I thank her all the time for sticking with it. It wasn’t THAT bad, but by 31 I should have been a bit more mature about things and open. It was a lot of childhood shit that I worked through in therapy. She had been in therapy for many years so recognised this in me and was super patient and cool about it.

    We were extremely compatible and I think her previous dating experiences helped her be patient with me because I think she recognised the potential of this relationship. The sex was and continues to be fire so that helped. We are now 3 years in and I’m pretty sure this is it for me, marriage and kids soon.

    I think asking this question is extremely valid and something you need to consider. Relationships are hard, but so is finding someone you want to commit to. Tell him about your concerns and see. I would give it a crack and work on healthy communication from day one.

    Good luck! If you really like him, give it a go!

  21. Not every adult virgin has something horribly wrong with them. Dating is hard, finding serious LTRs is harder, and some people need that before they want sex.

    If he seems good, he probably is, give him a chance.

  22. i understand the negative thoughts but the issue you are creating is your own doing (understandable by experience), but dont get stuck in the negative. Why not look at it from a positive point of view?:

    * He isn’t influence by bad relationships
    * You can mold him to be the boyfriend you want to have, as long communication is good and you are able to talk things out.

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