Should I try to pursue this shy guy?

I am 24, this guy is 29. He is relatively inexperienced with women. As far as I understand it, he has only had a few short term relationships, with at least one of them being long distance, and another being a volatile one with a pill addict. I don't know about his sexual experience but it is entirely possible that he's a virgin still as well. Though we have met in person, it wasn't until we began to chat online that we become close -about 9 months ago. In that time we developed nicknames for eachother and the conversations got flirty or sexual as well. We live about 45 minutes apart by car, though neither of us is able to drive (for different reasons), and so he never made an attempt to hang out in that entire time. Just when I was ready to dismiss my crush on him and tell myself that our chats were just harmless fun, we ended up attending the same event one weekend. Despite seeming very nervous and quiet, he took the time to compliment me, pay for everything, put his arm around me, and give a quick peck goodnight. He said he really enjoyed the time together when we spoke the next day. For the following week or two he was very affectionate in chatting but has since been very absent (like only chatting 5 min per day sometimes). In the past he said he's really bad with women and also that he thought if we started hanging out hed get too attached "like a weirdo" and hate himself for it. I have had many relationships, with two being in the 3-4 year range. I also have a fair amount of guys who ask me on dates. I'm wondering if he is backing off because he is scared of how attached he feels from the time we spent, or because he's intimidated by my being a lot more experienced? Or is it that once I validated him by showing some interest he lost his? Since he is pulling back, should I show him I really am interested by pursuing him to meet up again, or do I let it fizzle out?


Most Helpful Guy

  • how about you just tell him how you feel about him?

    • I would like to, but I'm sort of hesitant now because of how he cut down on being affectionate towards me, and also because he says he wants to hang out with me but yet doesn't make plans. I know travel isn't easiest but I'm used to guys being a lot more direct than this and am worried he would reject me I guess, despite him having showed he liked me in the past.

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    • whats the status between you and him now?

    • I mentioned that I would like to see him/hang out again, and also told him that I was feeling as if he was no longer interested in talking/seeing me, and wanted to know if that was the case. He told me that he is interested in taking/seeing me/being physical and all, and made some increased effort to pay more attention to me. I also think he warmed back up to me a bit after, though he still hasn't made plans with me to see eachother face to face.

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Have an opinion?

What Guys Said 1

  • It sounds to me he feels like you're out of his league. He doesn't want to risk getting hurt. He knows you could have any number of people, but I'd bet he's secretly hoping you'd ask. If you like him and think you'd do well together, I'd probably show him a little of your hand, and let him know you like him and want another date. He's probably too timid to ask.


What Girls Said 2

  • Do show some interest from your side. From what you've said he seems like a pretty decent guy. There's no valid reason not to pursue him now, if you like him. If he still seems distant after you've shown interest then you can make a decision.

  • From your description, he doesn't strike me as the shy type. Shy guys will hqve a hard time getting close to you. Touching you may take them months. They often insult you when the mean to compliment you because they panic and words that made sense in their minds come out harsh. They will keep their distance until they truly get used to you which can take weeks to months. They constantly need to be reassured in some way that you do care for them... And are not just tolerating them... They seem very interesting and funny when texting /chatting but in real life they are very different until they open up to you and even then their inhibitions won't let them to be 100% who they are.
    If he put his arm around you and complimented you just like that, he might not be shy, maybe just socially awkward?

    • He does describe himself as awkward, so maybe that's the word I should have used... Though this weekend event was Friday night through Sunday night and he didn't show any signs of interest to me (aside from paying for me) until last minute Sunday night.

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