Bro. I am a 26 year old man who's studying for his GRE to go to graduate school. You're only 2 years older than me. You have your whole life in front of you. Forget about the girl who "didn't want to gamble her life away". Who'd want to be with a preppy girl like her? what happens when her engineer starts having financial difficulties? I'll tell you what. She'll leave him for a "real" man.

Forget about her. Dump your regrets and start anew. You have the present and the future.

Remember, OP, times are changing. If you were born 20 years earlier than you did, you'd probably have the house, wife, and the kids. It's not your fault that you haven't made it in your early 20s. Life is getting harder and more complicated by the second. Very few people; often with connections and favors, make it right out of college. It is not your fault, and it's not my fault that I make less than 20k a year. There are 2 gates into good jobs nowadays that pay. Internships and connections. When you're in graduate school, befriend all of your professors, kiss ass, and take as many internships as possible. This is what HR drones are trained to look for.

Forget about women for now. Improve yourself and they'll seek you out, then you'll get to pick a good one to wife.