It depends if the women know each other. If you just go round at school and hit on every girl you see then yes you will be labelled as desperate. If you are out in town then women aren't going to know each other so you can talk to as many as you want because they're always coming and going. If they see you trying to hit on a girl and then going to them then again yes they will see you as desperate. But you just have to sit and wait a few minutes for people to walk off and then try with new women.