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Trying to transition with a shy girl


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Here's my dilemma:

 

First some quick background. I'm 32 and she's 30. Neither of us has been married nor has any kids. We've known each other for two years and have been friends for a little more than one. We live about 90 minutes apart but work for the same company (in different locations). Alright, here's the deal...

 

A month ago "Kim" and I were talking via IM and we had the following exchange:

 

Kim: "I've been meaning to ask you, why don't you have a girlfriend? I've been curious for a while..."

 

Me: "Because I live in a town of old ladies. Besides, there's no one around here who is interesting. Why don't you have a boyfriend?"

 

Kim: "Because I can't find a nice guy around here, there seems to be a shortage ;)"

 

Since then, her and I talk all the time, mostly in a flirty way. I've tried asking her out a couple time but I've had an hard time trying to get her to go out for dinner. When we've hung out with friends, things are fine and she and I talk to each other, but she spends a lot of time talking to her friends. On one such occasion, her brother, who had a few too many beers, told me that she is crazy about me, is always talking about me, etc. I asked him why she doesn't want to get together one-on-one and he said she's really shy and it takes her a while to open up. I don't mind doing things with friends so she feels comfortable, but at the same time, I'm finding it hard to try to communicate with her how I feel because we're always with other people. How can I keep the romantic vibe going between us when we're always around others? I really like this girl, and I've got nothing but time, but I don't want the constant group atmosphere to cause me to enter the friend zone? Any advice?

 

Thanks

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You need to be more creative and ask her out to something more exciting than just dinner.

 

Do you know what she likes to do in her spare time? Find out and then ask her out accordingly one day. For example, if she likes crafts, and there is a craft show coming up, ask her to go to the craft show. Lots of possibilities depending on her interests.

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