OK here goes you are a guy, you just graduated from high school, you still haven't decided what career to take but you love meeting the ladies. Here are some jobs that can increase your "encounters". =D
1. Makeup/artist - Not much action here you need to pretend to be a sissy but at least you can get into dressing rooms.
2. Fashion photographer - Get hot chicks to pose for you.
3. Masseur - get those magical hands at work and get some massage courses. With today's fast paced stressful world the ladies need a good massage. Better yet be a fitness instructor/masseur to narrow down your choices to the hot stuff.
4. Custom lingerie designer - Study dress/lingerie making and get snug fit measurements for your clients. =)