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I want to let him know I'm interested. But not scare him off. Any tips please on how to do this?

Tagged as: Crushes, Friends, Online dating, Trust issues<< Previous question   Next question >>
Question - (18 April 2012) 3 Answers - (Newest, 18 April 2012)
A female United States age 30-35, anonymous writes:

I've been out of the dating game for a while, but I may be willing to re-enter it. I'm getting really confused by the signals a guy I'm kind of interested in is sending, though.

On the positive side, he just ended up buying a webcam purely on a "dare" from me (I was messing around an he said something smart ass, and I said 'Well then Skype me," jokingly, but by the end of the night he'd ordered a new webcam), we've spent a good few of the last nights up talking until extremely late (3-6AM), he invited me to start "hanging out" with his group of friends, and when one of his friends DID start talking me he made an off the cuff remark about how much he talks about me.

On the other hand, just in the last day or two--even while some of the above has been going on-- he's been sort of hard to engage, and any time I do talk to him I get the feeling I'm annoying him.

In short, the situation is a bit hard to read and to complicate things further, I'm not sure his self esteem is the best (he's also mentioned something about not being able to get me if he tried), so I'm trying to walk the fine line between letting him know I'm interested, not scaring him off, and not making a fool out of myself either...so if I could get some outside perspectives on this, it would be awesome...

View related questions: self esteem

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A female reader, anonymous, writes (18 April 2012):

He sounds keen and possibly a bit scared, either of involvement or rejection. Don't chase him or he might get worse. But stay friendly and maybe drop in a few subtle comments that let him know you are interested.

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A female reader, Starlights United Kingdom +, writes (18 April 2012):

Starlights agony auntJust be friends, take it easy, be fun and flirty. Thats all you can do for now is be yourself and enjoy his company, because you cant push him along. His self esteem is his issue.

Goodluck!

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A female reader, janniepeg Canada +, writes (18 April 2012):

janniepeg agony auntYou already showed him you are interested by talking three hours a few nights. His insecurity is something he has to deal with himself. He is at a point where he has to make the move before it's too late or when you lose interest. As long as you keep in touch with him that's enough. You don't have to do anything to make it easier for him. Both of you may need time to rest. No one can think clear when they are sleep deprived.

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