If you don’t try you get no one, but I think it must be kept in mind that asking a woman out on a date immediately changes your relationship with them, whether they accept your invitation or not. You’ve let a woman know that you are interested in being more than just an aquaintence, and she will let you know whether you’re in her league or not by saying “Yes.” or “No.” Saying “No.” to your request for a date is going to make any mentally healthy woman very uncomfortable because she knows you will be disappointed, so she may avoid you in the future so it doesn’t happen again. Or she might just think you’re a creeper, and then she will definitely avoid you. Even if the two of you are together again in casual circumstances, the fact that she rejected you will always be there, and that’s awkward. A realistic assessment of the possibility of a woman going on a date with you should be done before you risk the possibilty of never seeing the woman again, even as a friend. To get the best advice on whether or not to make a move, ask your woman friends who will probably know more about the lady in question anyway. But again, if you don’t bet you can’t win.