Hey, dude!

I've been there in your situation. Asked one of my closest friends out in HS, got a long winded conversation about how great our friendship was, and she doesn't want to ruin it. (Basically a crafty way of saying "no"). I was an awkward and shy kid, and plus I was not very confident or assertive.

I felt like shit for a few days, which I guess you must be feeling too. Things got awkward between us, and we stopped talking. My dude friends had a good laugh about how I got rejected in the most awkward way.

And then it happened, I don't know what you call that feeling but I bet you too will soon realise that it doesn't matter if she rejected you, thing is, you had the balls to try to approach her. So what if you failed? Everybody fails. Did you get everything right on the first try? You put yourself in a situation of social discomfort. The more you get accustomed to social discomfort, the more confident you get in such situations.

She's also a human being. She also might want to talk to you, but the awkwardness created is stopping her too. If you feel like talking to her just bloody do it. And never ever think any situation is awkward, just talk like you're talking to one of your guy friends. (No, this is not an excuse to say weird shit) If she doesn't want to talk, then leave her for the moment. Most people after a while do try to re initiate a conversation with somebody they declined because of guilt, and especially when you've been a friend of 3 years. If she doesn't reciprocate, don't take it personal. There are tons of women around you, and you're no lesser than any of them.

So what if you were embarrassed? Does it really matter in the long run? Is it affecting your life in any major way? No! You got a life ahead man, gotta get a career, win the Nobel Prize, climb Mt. Everest, whatever suits your goals.

If your friends make fun of you, remember its only temporary, people forget things.

And a personal anecdote: I asked one of her best friends for a date, around 3-4 months later, and she confessed she's been feeling that way for quite a while, and I think my confidence skyrocketed after that point. You'll get used to it too!

Obviously, you need to change your external appearance too. I can't advice you on this because I don't know you, but try to look as good as you can. Looks matter. Its more about looking confident and stylish that it is about looking genetically gifted. Plus, gym.

And don't take everything seriously. Life's not Titanic.

You got 70 years to live, don't waste it on just one woman.

Love yourself more than anybody else. You're the greatest motherfucker to walk on this Earth. Gotta be a cocky, arrogant bastard more than anything else.