Hang in there Humpert!
I just read your journal, looks like you have good looks and a good walk, which is very good - that means you've got your fundamentals handled, which is very important.
It's obvious though that your sticking point right now is approaching. I'm guessing you've already read all of Chase's articles on approach anxiety?
I wish I could give you more tips, but to be honest, approach anxiety wasn't that big of a problem for me. I just knew, I had nothing to lose. And the same goes for you: you have nothing to lose!
A lot of people here on this site (like Franco) mentioned that their biggest sticking point was approach anxiety as well, but once they got past it, they were on the high ground. No regrets.
After all, what's the worst that could happen? You get a drink poured on you (this isn't going to happen anyways, unless you're a real douchebag / really creepy and don't leave her alone after she shows she's not interested)?
A girl says: "pffftt" and looks at you angrily? So what? Find another one.
The other day, i went up to a girl and asked her if she was single. She looked at me angrily and said: "oh my god, I don't need this right now. if you keep talking, I swear, I'll spill my coffee on you."
Hahahaha, it was so funny. I just walked away smiling, cause who the fuck cares! She didn't want to talk to me? Fine! She was having a bad day? Good for her! You're never going to see her again anyways and if I didn't approach her, I would've felt worse.
Plus, looks are the most important, and it seems like you got that: I wish I was 200lbs (I'm like 5 ft. 9 and 130lbs - so pinner hahahah!) Then its vibe. Then its game. If you read Ricardus' articles on the success factor, he says that hot guys can go up to girls and ask them what time it is, and the girls will even warmly receive them.
The next time a hot girl walks past you, think to yourself: "wow, she could be my lover or my girlfriend," then turn around, and go talk to her! Fuck it! Nothing matters in life except for: did you try your absolute best at what you wanted to achieve?
I ain't no pro with women (yet) but I hope I helped!
PS. that part about the guy rapping about you and calling you mr. confident was hilarious! Today, I was walking downtown, solely focusing on my walk: slow walk, arms swaying, chest puffed out, head up, shoulders a bit back. And this guy walks up to me and says something like: "hey man, you got the swagger!" and then he started telling me about this credit card promotion. I told him I wasn't even 19 yet, so I couldn't even have a credit card. He replied: "oh, you looked like you were like 25". I responded: "Haha, thanks". So don't be embarrassed about your walk! It may seem like you're trying a lot, but it really makes you stand out from the rest of the crowd, and thats what you want. Just think to yourself: "Yeah, I dress like a boss. I walk like a boss, and I am a boss". Then go talk to some hot girls!