She's Shy, how do I flirt?

Visitor's Question from a 13-15 year old Male
im 17 and shes 15, and in high school thats a pretty big dfference. ive noticed her walking in the hallways and stuff so one day i started talking to one of her best friends so i could get closer to her. the problem is the girl i have a crush on is really shy....her friend that i was talking to tried to introduce us one day and she just walked really fast past me and covered her face. i dont know if that was a good reaction?? i seriously dont know what to do but i do think that it was cute what she did. shes so shy i cant even talk ot her, but my question is: what can i do or say to break the ice with her?? she is one shy girl!! Advice
While you may feel 17 and 15 is a big difference, seniors dating freshmen is a very common thing to happen and that's an even bigger difference. So the important part is that you focus on what you both are as individuals and not on something like age which will become pretty meaningless in a few years anyway. The real issue isn't her age - it's her shyness. She can easily be just as shy at age 17.

Very few people like having to "perform" in front of an audience. For a shy person it's even more like torture. So don't make her have to prove she's smart and friendly and fun in front of an audience! Instead, find a time when she's alone, where you can chat with her quietly. That way she doesn't feel the pressure of other eyes watching her, waiting for her to make a dumb mistake.

I have some hints for male flirting here -

but it all comes down to her feeling comfortable with you. You can't just leap into it and expect her to turn on to full volume like a radio. You need to build up the comfort level, build up the friendship. The more she realizes that you're a friendly, comfortable person to talk to, the less nervous she will be.

-- from Jenn
One of Your Friendly Advisors at

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