Improved self image... Confidence stays same old - same old?

Visitor's Question from a 16-20 year old Male
Alright, here goes. Thanks for your help in advance.

* Before I go on, I'll add that I'm a 17 year old Junior in High School. I'd like to be as completely realistic as possible in this situation. It is a new generation of people who use programs like AIM communicate for the majority of the time when not in school or in person.

Well, like most people would start out with. there is this girl who is VERY attractive (to me, almost "out of my league" perhaps) and is a grade below me. We have been at least acquaintances for the past 2 years or so, mabye a "hi" every now and then. About a month in a half ago, I was with a few friends (who were all men) and saw her with a few of my friends (who are all girls) and we talked for about an hour all together for about an hour, and that was that.
A few days later, she sent me a message on AIM that she really enjoyed being able to see me for the first time in a long time, and we talked via AIM for about 30 minutes. A couple days later she sent another message and we talked for a good hour or so.
Within a couple of weeks, messages every other day or so became almost a daily routine and we have become pretty good friends over the past month. Over the past 2 weeks, we have been going to lunch together a few times a week and she has called me and we've had conversations often times exceeding an hour and a half.

* Note that this is sort of a new thing for me. I guess I could describe my own situation as shallow as possible by saying that my last real "girlfriend" was ended in early 6th grade. My social status is pretty good, I have alot of friends, both guys and girls, but has always been known as the "cool guy" and never the guy to date. I have always been a little on the heavier side, but within the past 7 months I have gotten into good shape and have really gone to great lengths to improve my self image.

Anywas, so we have been talking about almost everything on a daily routine now, I often have lunch with her, we usually talk on AIM for a good 3 or so hours total between the time school is out and sleeping time. There has been one instance where we have really hung out outside of school when she said she wanted to go shopping at the mall and invited me to join her. I'd say that we had a pretty good time and got along great. I will say that vocally I was a little choaked up just due to being a little nervous.
Earlier this week she said that we should all hang out this weekend together (all referring to my group of friends and her). I just can't tell if she is just hinting at wanting to hang out with me at all or is just saying that to be nice.

So basically, over the past month we began talking to the point where it is a daily thing by talking either on the phone or AIM. There have been mabye a few (3-5) signs let off by her that actually hinted at flirting - in my perception - or mabye urging me to move things forward, but for the most part, it is all just talk of personal stuff, our friends, random events, and school. She tells me that I am her favorite person to talk to.
I know with some of the things I have said the answer may be obvious, but believe me. I have been in several situations where I befriend a girl and become a really good friend of hers and when it comes to asking her out, it remains "Just friends." There have probably been 3 instances of pure rejection, which all occured literally 55lbs ago - I was 6'1 255 lbs, now I'm 6'2 200 lbs. Being in today's world, you and I both know those 2 figures (height and weight) mean LOTS for starting a high school relationship, regardless of how shallow that may sound.

I guess what I'm asking you is, should I go for it? I don't think that my ego can take 1 more shot of rejection without going crazy, especially with a girl that I am this attracted to both physically and emotionally. My old threshold is now gona (weight) and even with a highly improved self image, my confidence is still at the same level it once was, 55lbs ago.
Another question would be, how should I go about asking her out in my particular situation? I have read almost every tip there is to read, but none really seem to be realistic for my situation. I'm NOT about to write a poem or have any telegrams delivered. No offense, that was a good idea back in the 50's.

I can't even express how good it feels to get this entire situation onto paper for someone who knows best to read. I'm so sorry it ended up this long, but I feel every word necessary to describing the situation.

Thank you again, this is truly a great thing that you guys have going on this website.

- G. (I'd love to refer to myself more formerly for you guys, just protecting my identity!)

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RomanceClass.com Advice
You have everything going for you so go for it.

Your age, height and weight and the way you two spend so much time communicating all suggest that she wants you to ask her out.

So it's not whether to ask her but how to. My advice is to take the direct route. Ask her if she wants to go to dinner or the movies "as friends." After several of these "friends" dates tell her you are "developing feelings" for her and ask how she feels about you. Odds are very good that she will confess that she has feelings for you two...and you can take it from there.

Good luck! George

-- from George
One of Your Friendly Advisors at RomanceClass.com

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