A
female
age
41-50,
anonymous
writes:Sorry if this sounds really lame but there's this guy that I'm crushing on yet I'm too shy to even hint that I'm interested. We knew each other from elementary school and just recently found each other online. He told me that when we were young, he had a huge crush on me (I doubt that means much after all these years) and the only thing I could say is, "Why didn't you say anything?" We had to be like eight so I felt dumb. Well, I'm naturally shy (until I get to know someone well), especially around guys I like but chatting with him online shouldn't be so hard but it is. I feel like I quickly lose his attention the few times we've talked online because I'm so freakin' shy, I can barely hold a conversation. We've seen pictures of each other, I can tell he likes what he sees and I definitely like what I see so why can't I step up to the plate? What can I do within my comfort zone to let him know I'm interested?
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female
reader, epifanatical  +, writes (9 October 2008):
 Just continue with your friendly chats sweetee but drop lil hints that you are interested. Remembering names, places, things you have in common are very impressive to a guy. Ask what he does now, what his interest are and stuff like that. Dont seem over eager, yet dont seem uninterested (i no your not, but try not to let your shyness get in the way for him to think you are) I too was in your shoes, being a shyster, (i think i still am in a way) I have not given friendships a chance in the past because of it, but I now just focus and say what i feel and whats on my mind, and stick to my honest feelings, and its slowly helping.
Why not bravely ask him on a group date? Invite others so you can be comfy, and go have a great time! There will be less pressure and it will give you guys a chance to catch up!!
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