The telling women thing is always a concern which comes up here pretty often, and it's something you have to accept as a consequence of your decision to wear--- but it usually never turns out to be that big of a deal in practice if you know the girls are into you and you look good in the piece... that's why you don't read about many problems, I assume. Just get it out of the way early.

In any case, I wouldn't let this one girl have that much influence over what you decide to do whether you get the piece or just get some clippers and trim all your hair short and close (which might look good on you vs. the combover.... who knows).