I (31F) started dating someone (32M) about a month ago. We’ve hung out maybe 5 times and text everyday. He’s super kind and generous, and we want the same things in theory (relationship, kids etc.). We also speak each others’ first languages as our second which I really enjoy. The problem is, I’m just not sure I like him enough?

In part I’m worried that it’s just because he is being so forward and obvious with his interest in me, which is not something I’m used to. I usually have to chase in relationships. So I don’t want to ruin something with potential because of my own weird anxieties. But on the other hand… I don’t find him particularly funny and despite him definitely being very intelligent, that doesn’t come across in conversations. I find myself not really engaged in many of our conversations.

I have a good enough time when I’m with him, however. And it’s not like I don’t laugh – he’s fun, just not funny. My friends think I should continue dating him and I will develop stronger feelings for him but I’m very wary of leading him on. I will be honest if he asks to DTR and say I’m not ready (and deal with whatever comes from that) but should I continue dating him casually? Will feelings grow? Or am I just wasting both of our time?

I would really love to end up with someone who treats me the way he treats me… but I’m not sure it’s him.

24 comments
  1. You don’t sound into him at all and it doesn’t sound like in a way that would change

  2. five dates and I still don’t find him funny, that’s a pass for me. humor is so important to me; both that I find him funny and he thinks I am too.

  3. If youre used to having to chase relationships then maybe that thrill and angst is what you equate with love when that isn’t what love is. Love is more settled and safe and often they say can feel a bit boring intially. Just an idea. The most I’ve ever been loved by a person was someone who made me feel very relaxed and safe.

  4. I feel like 5 dates is more than enough time to know if you’re truly into him or not.

    Let him down gently and move on.

  5. Have you had sex? If yes, how was it? If not, do you feel desire to do so?

    You don’t have to answer us, but thinking about these questions will usually tell you what to do in a situation like this.

  6. So are you uncomfortable because what he’s doing is different than what you are used to, or because you don’t actually like things about him? It’s hard to tell if you are pushing away from fear, or if there is more.

    But usually by 5 dates of so one has a good idea if they want to continue to explore a relationship or not. The fact that you are dreading the DTR convo is concerning. The important thing to figure out now is why. It’s okay if he’s just not your type of person. Just don’t assume because it’s not infatuation it’s wrong.

  7. I recently started dating someone I wasn’t sure of, and was having the same thoughts as you. I carried on seeing him because I thought, why not be treated nice and enjoy myself for the time being? Any way, after 3 months my feelings did a complete 180 and now I really like him. Some things just take longer to develop , so it’s your decision whether you want to continue and see if things get better or to cut your losses early.

  8. Yeah, I’d bail for the time being at least. I spent 6 months with my most recent ex, my mind just was never engaged. Felt like hanging out with a 6th grader sometimes; we just didn’t gel in the intellectual sense despite him being objectively intelligent at least at his job. He pursued me a TON and I spent the whole time trying to talk myself into it/not wanting to throw out a good guy for stupid reasons.
    Not feeling it with someone is a very valid reason. You can’t force it.
    Step away, maybe some time down the road your feelings will change but they won’t when you’re expecting them to.

  9. You may want to look into attachment theory. Has your desire to chase resulted in relationships where you feel like your partner is constantly pulling away and you have to constantly chase? There’s some really interesting science there. Like someone else said, healthy relationships are often boring in the beginning. May want to give it a little more time. Or not lol, up to you in the end.

  10. Sounds like you like lots of things about him… but that you don’t like him.

    You’re in the stage that is supposed to be the easiest to like the person. You’re going out, you’re doing dates and activities, you’re having fun when you’re together. Or, at least generally are in those first date days.

    Take a serious look at who you both are. Are you going to laugh with this person in the grocery store? Are you going to look forward to coming home at night so you can just be near them? Are you going to get a little smile when you think about them or when they send you a silly text halfway through the day?

    If not, you’re settling on someone you’re not really into because they check the proper boxes in other ways… and in my opinion, it isn’t going to work. Or, at least, it isn’t going to work as well as it could with someone you just feel the magic with.

  11. Does he try to be funny and you don’t have the same sense of humour? Or is he just not a person that tries? I don’t think my partner is particularly funny, he’s a lot more serious than me character wise, he’s also not a very flirty person, which I am.
    Yet we laugh about things all the time and I love being around him.

    It took me a little while for me to warm up to his communication style which is very different to mine. Though those thought of ‘maybe were incompatible?!’ Only happened in between real life dates, while we were texting, since he’s a very dry and ‘matter of fact’ Texter. In real life i always enjoyed his company and the sex has been awesome.

    Ask yourself if you’re actually excited to see him, and if the lack of enthusiasm is due to a different communication style or be user of actual incompatibility. You can also explain to him what you’ve said here, saying you are so many benefits to him, but he also seems a bit dry to you and you’re also used to relationships starting differently.

    I had a talk with my partner to say I was starting to get the sense that I might lose interest because we were so dry in texting and we were only able to meet once a week or so, and it felt really hot and cold, and he got exactly what I meant, and changed what he could to accommodate my needs, and just having that conversation and seeing this person is attentive to what I ask, despite doing nothing wrong and just being himself, made me feel a lot more comfortable in general.

  12. I once dated a guy I thought I “should” love for two years! I kept hoping I would love him because he was wonderful in so many ways. Without love, however, everything finally fell apart.

    I can’t tell you how long to wait to know whether or not you are in love, but I know that waiting won’t make it happen.

  13. I genuinely feel like “being used to the chase” and not understanding how ridiculous this is in relationships at 31 is a pretty big red flag.

    You should have a more mature perspective on dating at this point, IMO.

    To be honest, it sounds like you should let this guy go.

  14. This is a thing I’ve grappled with in my past LTRs. It’s a gut feeling right? Like you know that he would be good enough. I mean you used the word enough a few times on your OP.

    These are the questions I ask myself now:
    Am I choosing from my wound or my worth?
    Are our core values aligned?
    Most importantly, do I like myself when Im with my partner?

    Mostly, it is instinct. Everyone has told me: when you know you know. And it sounds like you know.

  15. Does he bang good? How’s his job and apartment?

    I’m kinda lukewarm on this dude. Nice isn’t really a personality.

  16. He doesn’t seem like he does it for you based on what you’ve said. You should break it to him gently to avoid stretching this out longer than needed. Good luck! ❤️

  17. I went along with it and seven years later had to extract myself from an engagement that I realised I just didn’t want to be in (even though everything on paper was great, I knew I just didn’t feel the way I should have done). If I’m honest with myself I think I knew this from the start. I’m sure that feelings can develop over time, but perhaps with less conscious effort? Having this much doubt is, in my experience, not exactly a green light.

  18. I have a feeling he picks up on your doubt as well. Speaking for myself and recent experience on 2 dates, I pick up some doubt but also interest from my date. I’m waiting it out with a few more dates to see because I know I feel good when I see her in-person so why stop/ I think my feeling will grow because I like what I see (i.e. positives outweigh the negatives). I might appear to be slow in picking things up but at my age, I’m also not completely ignorant.

    Don’t worry about leading him on. He has the choice to stop it as well so don’t burden yourself with that. A long shot, how about imagining him as part of your daily life? Is there still joy without being “funny”?

  19. it blows my mind people go on 5 dates and still havent had sex yet. like what are you guys doing

  20. I personally believe the first few weeks/months of dating someone should be brimming with mutual attraction & chemistry (which can happen without “chasing” in a healthy setting), but that’s just me. Life is too short to be with someone you feel lukewarm about.

  21. Twice I’ve fallen for men I initially wasn’t attracted to. First was a dear friend and second was a friend I didn’t really like til I got to know him.

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