I have two relationship questions that I was interested in getting opinions on: 1. Is it ever a good idea to ask out a woman with whom you have a semi-professional relationship (such as hairdresser, masseuse, personal shopper, personal trainer, etc.)? Â This seems like a gray area between asking out the cute girl who serves you lattes every morning at Starbucks (go for it.) and asking out your attorney (what are you crazy?). Â The big concern here is that if the personal relationship doesn't work out (or doesn't get started at all) the professional relationship could crash as well, which would be very unfortunate if she is good at what she does. 2. If the answer to question 1 is yes, what is the best way to determine her current availability without tipping your hand, keeping in mind that she makes frequent references to her ex? These questions are of course completely hypothetical and for discussion purposes only.