Just don’t know if I should accept my loss and move on

I (F23) met this cutiepie Jack (26M) in May and he was VERY shy. I found it adorable. Unlike any other relationships/attachments I’ve had, I had to consistently keep the ball rolling for us. One day things are getting kinda steamy after a night out and I was completely mind blown but how direct, forward, outgoing and just plain SEXY my shy man was. It was the most turned on I’ve even been by a man and we didn’t even have sex!

Within the next week though, I get a little fed up of always having to initiate and break things off. He’s deeply apologetic and tells me “you know I’m shy, you’re just so out of my league I get scared” blah blah blah which was honestly just? Annoying because I’ve done nothing but try to work with him on it and it felt like I was going above and beyond and he wasn’t trying to meet me in the middle.

A few months go by, I occasionally see him out (whenever I do he has one of his friends text me “omg is that you/ are you out” rather than texting me himself, even though I TOLD him my problem was that he was never direct).

In this time where we aren’t seeing each other, I think about that one steamy night a lot. I mean it really was just that crazy. So a week ago I text him asking him out again, kinda just grazing over the fact that he’s likely still shy so we’ll likely still have the same problems. Just wanted to get laid. We go on the date, everything’s going well, then we have sex.

And my god it was awful. None of the energy from our previous bedroom encounter was there. He was nervous, which in turn made me really nervous (I almost felt like? Because he was shy and I was having to lead that I was “forcing”? But we had a talk I know I wasn’t) and it was just not- we ended early and no one finished. I didn’t spend the night.

I can’t really believe it as we had SO much chemistry the first time. My questions is has anyone been able to come back from an awkward experience? My concern is that because he’s shy, if I try to talk to him about it so we can move on he’ll just get even MORE in his head. I just don’t understand why he lets the shyness get in the way, I have tried everything I possibly can to make him feel comfortable and it’s annoying that I feel like I can’t have open conversations with him because he may clam up randomly. I’m sounding bitter, because he is otherwise SO kind and thoughtful and considerate. I’d like for things to work with him but just not sure if that’s possible?

Maybe this question is moreso about making things work with a shy guy when you’re very outgoing yourself.

Thoughts from an outside perspective?

TLDR; had sex with a shy guy who previously seemed to have very good sexual chemistry with (we never slept together before). It was awkward, and I don’t know if it’s possible to come back from?

3 comments
  1. It sounds to me reading this that there could be some trauma for him. And things like this can be fairly difficult to talk about or open up with. I myself tend to start out shy sexually with a new partner because I’ve had a lot of past childhood trauma in regards to rejection, and then I dated a woman for about 3 years in which sex would happen once, maybe twice a month if I were lucky. A lot of that just combined into being unconfident about myself when I first start out. Second guessing myself, how far is too far or how fast is too fast, is she going to have a higher drive than she says or does she have no drive despite her saying that it’s high. There’s a lot of nervousness and anxiety that it’ll have me physically shaking from the anxiety if I’m unsure if it’s the right time to make the first move. But after some adjustment to have a better feel for her desires and appropriate times, I’ll end up being the one constantly initiating or teasing throughout the day, whatever it may be. But either way, there is that starting point where I have that bout of lacking self confidence.

    What I would recommend if this is a guy you feel is worth being with not just because of sex, then show some patience with him until he’s comfortable enough to initiate things on his own. I’m not saying to just completely ignore him because of it, just don’t try and make it overtly obvious that you want him to take him. Send him subtle messages throughout the day or week, things about how you want to experience the “little things”. Let him know that you’re thinking of him. If you’re approaching a date night, then let him know how comforting it is for you to feel the anticipation of him just holding you in his arms as you cuddle. Words of affirmation essentially. Just let him get comfortable with knowing that you want him and then when you do have the opportunity to get intimate, just keep it slow and build up from there.

    If he doesn’t show any kind of change after some time (more than just a couple of weeks), then think about bringing it up to him, but in a non confrontational manner. Something that has the effect of letting him know that you want him to be comfortable enough to initiate things and what would help him be able to get there. The biggest thing to remember is that however you bring the conversation up, do your absolute best to not be confrontational or aggressive about it because you’re either going to push him into a further withdrawal or experience a complete shift from this sweet and caring personality into something extremely dangerous. It is very possible to be delicate to his issues while being assertive about your desires.

  2. I think you’ve done everything you can really, you can’t force someone to change their personality. Especially if it’s self confidence/insecurity driven

  3. Some people click instantly in the bedroom. Who knows how, but I think it’s rare. Most couples have to learn how to have sex *with each other*.

    I married a shy guy by this definition— I genuinely emailed him after our third date to ask if he liked me “that way”, because I couldn’t tell and he hadn’t even held my hand. The first kissing was amazing, but each new thing was awkward as hell until we got it sorted out. He hadn’t done any of it before and most guys aren’t watching porn that covers an entire encounter. He had no idea what he was doing, what he was “allowed” to do, and so on. There were total fails along the way. Lots of trying Stuff that he had no idea whether or not he would like it (liked the idea from porn, but reality was complicated). Reality is sticky fingers and wrong angles, unexpected smells/flavors, and being sweaty. The cat wanders in an jumps on the bed with you. One tiny change in position suddenly results in a return to “resting position”.

    The key is that we really liked each other and wanted to figure it out together. Tenacity. Not repeating Stuff that went sideways (literally?) and focusing on the wins. If you like him, keep trying and use his name as much as possible to re-affirm that you want *him* and you’re with *him* in the now and on purpose.

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