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Posted

Anyone here ever date a really shy guy? I've been talking to a guy I've known. He's been flirting with me a lot and asking me if I'm seeing anyone so I'm thinking he's interested. But making conversation with him seems kind of difficult. I feel like I'm the one who has to keep the conversation going. He banters with me a lot and I'll start conversations but it usually ends in banter instead of him just talking. He doesn't ask questions so it makes it hard to keep a good flow of conversation. I really think it's just because he's awkward.

 

I'm a bit shy myself so it's kind of hard for me to be a chatty cathy. Some women are really outgoing and can handle things like this better.

 

Anyone here ever date a shy guy like that and have to keep the conversation going? How do you handle it? Say he doesn't ask very many questions such as "how is the new apartment...how is the bowling team going...." Do you just blurt things out and tell him things since he doesn't ask?

Posted

A shy guy could have more substance than an extremely out-going guy. An extremely out-going guy, where words come very easily to him, could have said the same thing to many women, in other words, he could be insincere. Too many compliments during early dating from a guy is a red flag, that he may be a womanizer. Give quiet guys a chance. Perhaps you could ask him questions, about his hobbies, school, where he has traveled, etc. It is OK if there is a lull in the conversation at times.

Posted

You could tell him how things are going with you without waiting for him to ask. And you could ask him leading questions and start conversations from there.

 

I find it hard to talk to EXTREMELY withdrawn people, but with most, I will happily natter on and know their life history inside a couple of hours.

Posted

A 'shy' guy doesn't overtly flirt and ask you if you're seeing anyone. That's the antithesis of shy. He sounds more socially awkward than shy. There is a difference.

 

If conversations are difficult, then 'getting to know' will likely be similar. I'd pass.

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Posted

He doesn't sound extremely withdrawn or shy especially if he is flirting with you etc. More than likely you are just expecting too much out of chit-chat or maybe he's just not very good at BS. You need to ask leading questions, if you know something about him (what he likes, doesn't like) then it shouldn't be hard.

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