Positivity and the big picture, my friend...
1. She already has a boyfriend.
What if she doesn't?! And if she does, you can definitely get her anyway
2. It's too late to approach her. I've seen her multiple times before. I won't have any chance since I should've made my move the first few times I saw her. The right time has passed.
You're psyching yourself out. You don't have to roll up like James Bond out of nowhere, with perfect game
3. She'll think I'm too awkward.
She probably will, but the girl you approach after doing this 100 times won't think so
4. She'll be nice and friendly and show interest, but that interest will turn out to be fake and she'll end up hurting me and using me without giving me sex and/or a relationship.
WTF.... Or she could end up on your ****... use a condom. How can she possibly hurt or use you without you letting her? My guess: You're afraid of her saying something like "Oh I was just being polite, you're one ugly son of a ***** and such a pathetic worm", to which you would agree, apologize for hitting on her, feel like you were kicked in the stomach, go home and berate yourself in your head. You gotta be unstoppable, emotionally. If a girl said that to me I'd laugh cuz I have already come to terms with my insecurities through equanimity and meditation, as well as countless rejections and many insults (not saying I'm great or perfect, just sayin)
Probably, none of this stuff will make sense right now. My advice is to experiment with meditation, cuz being able to make your mind go blank is useful. Also, read Casanova's autobiography, which you can find online through a Google search. (Skip the non-girl-related parts)
5. This kind of goes with 4, but she'll end up hooking up with one of my better looking or more suave friends instead of me. And I'll be sort of like the bridge for her to get them. So by approaching her I'll end up getting my friend laid instead of myself.
If this happens, take it as a learning opportunity... You should copy your suave friends
Honestly what will make you happy around women is understanding them, and Casanova's autobio is good for that. Girls love sex but always resist it and you have to lead them to it. It's amazing when you're just like "**** it, I'm going for it... If she doesn't want to, she won't let me"
You really have to LEAD because girls DON'T... they rarely lead an interaction into sex. If they do, they usually do it through the context of a relationship, making you into their boyfriend. But in the meantime, while you're waiting for that to happen, you have to make things happen yourself... If you decide for the two of you what is gonna happen, then she will have the choice to either follow, or resist... Just try it out because they OFTEN follow and it's amazing every time.
SO how do you use this advice? Well you should experiment with it, so that you see it firsthand. Realize that girls are not gonna bridge the gap for you, and neither are guys... No one is gonna get you laid until some girl chooses you as your boyfriend... or until YOU start doing stuff...
So just say **** IT, I'm gonna do what I want to do, and go talk to her, kiss her, caress her, tell her to follow, tell her she makes you horny, etc. The more you can PUSH the interaction where YOU want it to be, the more it WILL go that way.