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So there's this girl i know who is very beautiful, but so many women have turned me down in the past that i dont even think she'd say yes, disclaimer: i have no intentions of asking this girl out i just want to know your opinion
Yes it's normal to have such low self-esteem. Everyone on IIN does or else we wouldn't be here, trying to fit in somewhere. They'll all deny it, but you, me, and they know it's true.
Well then if you already know that she will say no, what do you have to lose by asking her out. Nothing. So go for it. Keep in mind that no matter how pretty you think she is, someone, somewhere is tired of her shit.
Beautiful women are surprisingly more grateful for the attention because most guys think along the same lines as you, that "if she's beautiful she must have high standards" so they tend to be intimidated.
Just go up to her, say hi, pay her a nice compliment, and offer to by her a drink. You may just surprise yourself.
It seems to me there's a difficult line you have to walk.
On the one hand, if you're sure she's going to turn you down when you approach her, that minimises the painful feelings of rejection you'll have if she does, but it also means you'll be giving off negative vibes and she may well pick up on those. It's also possible you'll subconsciously self-sabotage and hear yourself saying something incredibly obnoxious or stupid.
On the other hand, if you convince yourself that she's going to say yes, you might come across as cocky and entitled, and lots of women don't like that. (But some do, which only complicates things more.)
It seems to me the best approach is try to be yourself and do your best to act natural. If you don't appeal to her for whatever reason and she turns you down, it's not the end of the world. She's just expressing an opinion based on her less than perfect understanding of the person you are. Being rejected by her wouldn't mean that you're a horrible, ugly, despicable person that no woman would ever want to spend time with. It simply means that, at that particular moment, one particular woman doesn't want to be with you.
However, you say that a lot of women have turned you down in the past. It might be worthwhile to try to figure out why that is. How you can do that might not be easy, but if you have women who are friends, you might consider asking for their views.
If you approach a woman thinking that she's going to turn you down is self-defeating. Approach her with the attitude that you don't care if you get shot down. This should make you feel better and give you a look and attitude of confidence. If you go expecting to be rejected then you will be. This will just decrease your feeling of confidence and further affect your low self esteem. I was like that until I realized that beautiful women are rarely hit on because everyone thinks they will be rejected. I started walking up to women and complementing them on something like their hair clothes anything.
"I was on the other side of the room and noticed your hair. It looks great." That has GOT to at least get you a response and a door opener. And be yourself. Don't try to be someone you aren't. Women pick up on that real quick. Good luck.