how do i deal with an inconfident girl?
negging would crush her.
so do i do the opposite? compliment her? say your eyes look nice?
I have tried asking for her opinion on different things, like my clothes (does this look good on me?) or her job (how do you like your job? would you switch jobs if you...)

but to my surprise, that doesnt seem to turn her on. I am inconfident myself and i love it when someone asks my opinion.

she is not responding to my playfulness...I have tried being playful but i think she doesnt want to do anything that is not "socially appropriate"...she is too polite...I dont know whats her problem and i dont know what to do.
or when i say something she just repeats what i said as a question
like "i like pies?" "you like pies?"
can you tell me what her problem is?

When a girl returns questions I say she needs to answer first and then I'll shut the fuck up and wait until she breaks. Which she will in about five seconds. Give her a blank stare and she'll crumble which gives you value.

wow, she sounds like a boatload of fun

i don't understand why guys think it is their job to fix the hangups of girls around them

nexxxt

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what dr. house brings to medicine, i bring to everyday life (an extreme dose of cynicism), don't listen to the curmudgeon!

Dude she's obviously boring as counting beers on the wall..

Why is it you want to talk to her anyway?

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An extra post just to say that this is utter bullshit. Girls got filthy mouths too, you'll just have to learn how to address it. Even the shy and insecure girls love sexualization.
Again the easiest way to get a girl to talk about sex is by framing it as not a big deal.

because she has big boobs and i want them
she is in my acting class and we are doing a scene together.
guys, can you suggest some ideas? i have a lot of freedom here because i can always say its my character that's doing those things.

A real man would never apologize for his explicit sexual behaviour and he would certainly not hide it behind some character.
And ideas: well get her to talk, about herself preferably. Don't do try hard stuff, just some genuine interest mixed with showing some intent will do.