WOW! It is such a coincidence that I stumbled upon this thread. I have been feeling the same way as you in the past month.
I have been beating myself up over not going to a university after high school. I too lost a parent when I was 16 (my Dad), and it stunted my development a little. I lost direction in life. I got into a decent college, but I decided to go to a community college instead. I am now 21.
I went out with this girl who goes to a university, and is in multiple clubs. I felt inferior to her because she is graduating in a month, and I still have two years. Now, she seemed average as far as intelligence, but her education so far holds more weight. So I definitely know how you feel. I think the reason we feel this way is because it isn't normal for the woman to make more than the man- and it can hurt our pride. If a girl has a degree and you don't, chances are she will make more money than you will...so it bruises your pride. That's all.
I was in GATE and Honors programs ever since I was little, so I feel like I failed myself in a sense by not going to a university. I shouldn't, because there are many smart kids at community college. I am transferring in the fall, and this is my last semester at community. Once I get out I'm sure I'll feel fine.
We are young and we don't have our lives figured out yet. We aren't 100% sure of who we are, and we don't have a career yet. This is why it messes with our heads more than some of the older members on this board.
You have to realize that most people don't go through what you did. Some of them do, but not all. Hell, I could have gone to Stanford but I didn't. I messed up. I'm sure you could have gone as well. There are plenty of people in community college that are in their late 20s and 30s. Also, there are people that have gotten out of the military (mid 20s) that are just starting school. I know it's hard but DON'T feel inferior. You'll get your degree, and you'll be on the same level as all those women with degrees. Work hard and keep your chin up. And remember, a degree doesn't show that you are smart, it shows that you can work hard.