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You remind me of myself a few years ago. I learned the only safe way to let go of my anxiety actually and move forward on personal relationships was being a cheapass and outright showcasing interest and flirting right off the bat with a LOT of girls. A lot of girls will appreciate the attitude if you manage not to pass as a weirdo. You can leave the friendly talk for later if she responds on a positive fashion.

I'd try to flirt more on your case rather than stand the risk of eating someone's dust. Because if that happens, believe me, even if you get her in the end, the psychological malaise of remembering her past relationships, while you were still asserting the risks, will eat you from the inside out.