New in love

Visitor's Question from a 16-20 year old Male

I have been reading articles/tips on this site for a while now, and I've decided to personally ask for some specific advice on my toubles.

I've had a crush on this girl for a while. Unfortunately, I am very shy and have trouble talking to her sometimes. We are friends, but aren't very close. She is also more popular than me, but we still talk to each other, and she is the type of person that doesn't care about the superficial high school clicks( which in our school aren't that bad. some of my friends are very popular ).

I'm not good at flirting, but I try. Lately I've been noticing that she has been glancing back and making eye contact for a few seconds, but I can never tell if she is flirting. I also get nervous and quickly break eye contact because I don't know if she is actually interested in me or is just looking in my direction. I don't want to come off as creepy.

I don't feel comfortable asking her out because I feel like she will reject me, and I don't know if I can handle the rejection. I've never had a relationship before and I feel that she is out of my league. plus I am very shy and I don't want to humiliate myself. I have the feeling that she will think it was just a "cute/nice" gesture, but would never actually take it seriously.

Is it a good idea to have a friend tell her that I'm interested, but not ask her out for me ? Also, what would be a good way to go about this( for example: my friend--"Hey, [crush]. Did you know [my name] likes you? I think you two would make a cute couple." ) Would this be a good way to let her know that I like her, and finally find out if she has any feelings towards me?

* Please keep in mind that I am truly clueless about this whole dating thing, and that any advice you can give me is a huge help. Thanks in advance! Advice
First off you have to work at improving yourself. Think of your personality as a muscle or sport where you have to use it to get better. You have said you are shy, not good at flirting, nervous, uncomfortable, and clueless. These are things you have to change. The way to change is to keep trying until you get used to the usual confusions, rejections, etc. which everyone endures. What makes you think you are so special that only you have these symptoms.

Before thinking of asking her out, take these simple steps to improve your relationship. Whenever you pass her in the hall, look straight in her eyes, say in a clear voice "Hi" [her name], and give her your best smile. Whenever talking with her always smile unless she is talking about something sad or disagreeable. After a week or two ask her to go to a movie, a walk, sitting in the park, or just hanging out.

After you go out with her once or twice you can tell her you like her and ask her out.

Good luck... this will take work but as they say "faint heart never won fair lady."


-- from George
One of Your Friendly Advisors at

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