How to Approach NT girls/women?

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Hi, I'm Anthony and I'm 17, and as you've probably guessed I have Asperger's. I live in a small town where not a lot of people, my own family included, are not really all that aware or educated about mental disabilities/disorders, and most of my peers are NTs. There's a girl that I want to ask to the upcoming homecoming dance but, I feel like it would be very random as I am what you would refer to as the "Loner" type who tries to establish normal relationships with people but am left out due to my lack of social skill, and random due to the fact that I never talk to anyone in their social circle, which is all female (which I find to be absolutely mortifying) how do I approach the group to talk to her? I also tend to say very inappropriate and/or dark things because I have an off sense of humor, so if you could tell me how to avoid those comments while still entertaining her attention and my own, I would heist grateful and hold you to be in the most elevated echelons of internet advice! Thanks, and may you Live Long and Prosper!!