What a newly divorced 40 something man screws. She is between the ages of 23-27, not super bright and works as a waitress or bartendar at the bar he frequents, because he has no
real friends or
social skills. He hits on her because 1) he thinks he's cool because someone 20 years younger is attracted to him (ie: his money) and 2) because she is the only female he sees
on a regular basis. He can "stalk" her and she doesn't even know it because he is a permanant fixture at that bar.