This is an interesting topic and I'm looking forward to seeing some of the replies
I am aware that here in the UK plenty of women go to nightclubs where they know that male 'celebrities' will be - eg premiership footballers etc - hoping to get picked up by them. That seems quite a predatory thing to do IMO but seems to be socially 'acceptable'
So the question of "how far is too far" is very interesting. I'm going to spend some time thinking about this and then reply more fully but in the meantime I suppose if you were to set up something like this near her home it would be ok wouldn't it?