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Socially awkward boyfriend

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I find it hard to explain this but I'll try my best. I've been feeling really drained and irritated by my bf. He's a nice guy, but he's coming across as socially inept. I know not everyone is super out going and confident, but we've been together for a while now and nothing seems to have changed.

He can't really make conversation or keep a convo going. He only asks me simple yes or no answer questions, and it'll be the same ones all the time, and there's only so many times you can be asked the same thing until it gets irritating. For example a few months before going back to Uni all I got every time we hung out was "so you're going back to university soon" "yeah".... "University starts back soon" "yeah it does." Now I know I could say more and he's maybe trying to lead it to something, but there's only so many times I can give an answer to the same question.

I dunno if it's cos we don't have much in common or if it's him, he's maybe really nervous or doesn't really know how to socialise. I don't want to seem like I'm being too hard on him or nit picking. It's beginning to really make me feel crap and I dunno why. I hate being the initiator, otherwise we sit in silence. I don't feel like there's any spark or excitement. When I'm with him, after a bit I want to be by myself, like I get this feeling of wanting to be left alone. And I don't think that's a good sign at all. He'll say he missed me about 5 times in one day. And it's like yeah you said it once already... And after he says it the first time I don't say "I miss you too" to the rest because I think if I don't say it he'll get the hint to stop saying it several times, but he doesn't stop.

I told before I want him to initiate more stuff and take control more, but somehow he's confused that with being clingy and needy.

I dunno what to do. I think he'd take it really hard if I broke up with him. But it seems worse to continue and feel this crap and drained, and to stay with someone just cos you don't want to hurt their feelings..

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