What is the meaning? Could it have different meanings?

[Anonymous]

If a girl tells a guy he is not a “pretty woman”, is she saying he is not good looking? Or is it leaning more to the fact that he is not a woman and all?

[SteveSmith1985]

I don't know if I understand the context here. More detail would be helpful.

In general though... if a girl tells a guy he is not a pretty woman, it's going to imply that you are acting like a stereotypical "pretty woman." She was calling you a bitch dude. (calling you a pussy). Saying "don't be such a pussy" about whatever she was talking about. It's like saying "be a man." Or "man-up." It's nothing at all to do with your looks, or attraction.

It's possible the details of your situation would change that... but in general, with no context this is definitely what that means most of the time. (but not as aggressive as straight up calling you a pussy. Same sentiment though)