DID SHE RUIN HER CHANCES?

Dear Jellybean,

Ok, so I have a guy friend who I am quite close with. He is very sweet and I met him last year. He was also kind of "nerdy" and I never saw him as more than a friend. We weren't all that close last year but now we are. Last year I had a boyfriend, only for a month and it wasn't that serious. I broke up with him because I wanted to be single. So then after I broke up with my boyfriend, my guy friend asked him out. I turned him down. I admit I didn't handle it very well. This was in July. So, I didn't see him for almost the whole summer. Back at school, he is now very cute and popular and has girls hanging off him all the time, which can be quite annoying, especially while he is talking to me. Since school started I have developed a HUGE crush on him. It isn't because of his looks, it's just that we've grown closer. We talk a lot on MSN and I learned that he has had so far only bad experiences asking girls out. So now I felt horrible about turning him down. So now I like him a LOT but I think I might have ruined my chance with him. How do I get him to ask me out? We are both very shy. Help me Jellybean!!
-Confused Canadian

Dear Confused Canadian,

I've got an idea for you. Next time you're talking to your guy friend, mention another friend who's recently broken up with some guy. Tell your guy friend, "She says she'll never date another guy again." Then say, "I remember feeling exactly that way when I broke up with (your ex's name). She'll get over it though, just like I did."

Then you can bring up that time he asked you out, and hint that you're sorry it was such bad timing, because if you weren't fresh out of a breakup, you probably would have answered differently. Use your own words for all this, of course, but you get the idea.

After that, it's up to him to catch the hint, and ask you out. I don't think you necessarily ruined your chances. If he learns that your rejection wasn't personal, and it really was about timing, he might just give you a second shot. Good luck!