LostSoul said:
That's a really bad idea. If you become "friends" with her, you're going to have to change the whole dynamic when you tell her you want something more. You don't want her thinking of you that way.
I have to agree with this statement wholeheartedly. And also disagree. Wholeheartedly.
Let me explain.
I'm 31, and was never exactly what you'd call shy. I easily fit the definition of an extrovert (Heck, I acted in plays and played in a rock band), but when it came to asking girls out I was very shy and afraid of rejection. So, naturally, I got to know lots and lots of girls, many of whom were some of my best friends throughout high school and college.
And after talking with most of them years later, I found out the same thing almost across the board. "If you would have asked me out when we first met I would have dated you. Now that we are friends, though, I just don't see you in that way." I never realized that I was attractive at that time, but now that I'm 13 years older and weigh about 100 pounds more than I did when I was a senior in HS, every woman looks at pictures of me from high school and tells me how hot I was.
Now, here's the "I disagree" part. I met my wife 8 years ago. She had just gotten divorced and her husband had left her when she was pregnant. She needed a friend, and that's what I was. Then we became more. I have recently seen other women who are a bit more mature make the transition from friend to girlfriend quite well, and they are some of the best relationships I've seen.
Most High School girls (and many in college and beyond) aren't mature enough to make that leap, from friend to lover. I sat around and watched all my female friends for years date jerky guys for years on end, but the same girls would meet a nice guy who they could be friends with, and they would break up within about 2 weeks. Judging from my high school experience, I think she's more likely to go out with you if you walk up to her confidently and ask her out rather than trying to be friends first.
And back to the "However's", I never stopped trying to be friends first. I knew that when it really worked out, I'd have the best relationship I could possibly have. And that's what happened. My wife is my best friend, and I wouldn't have it any other way.
So, I guess what I'm saying, is do whatever you want to. Ask her out, or don't ask her out. Be friends first, or don't. If she turns you down, or if you don't ask her out at all, you'll be eaten up by regret or pain for a little while, until the next time to encounter this feeling. Because it will happen again. Everyone talks about taking opportunities when they come along, but I've found that there are always opportunities out there if you keep you eyes open.