1. You should live your life for what you want–not to get dates. You’ll find a girl who appreciates you for what you are. Besides, the girls who want guys planning to work want guys with a good plan, and you aren’t going to get a very good plan by going to some yeshiva for 19 year olds and taking liberal arts courses.
2. Got no advice on that. If you aren’t ready to go to college, then don’t go. Find a career that doesn’t require college. Maybe become an auto mechanic. Or an IT guy and learn it all for free on the internet.