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Again, from the female perspective, it's hard when you have a male friend who is always trying to jump the ladder from friend to boyfriend. After two or three unsuccessful attempts on his part, you start to wonder if maybe you're just not being clear enough when you say no, or if you're somehow giving him unintentional mixed signals, or if he's some crazy stalker who's never going to accept that you only like him as a friend. Also, if she had changed her mind since the last time you asked her out, you'd probably know it. She'd start dropping little hints like, "Remember when you asked me out that one time? I was stupid for not saying yes." Little things like that.
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Second this. I also had a VERY good friend whom I lost because I was too chicken to say "I like you a lot but I have no intentions of dating you."
If she's declined few times already and you don't mind staying good friends, keep it that way.
Jam it back in, in the dark.
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