Some things to consider.

So love conquers all. Mostly. But how much?

would it conquer:

1) the fact that your guy is earning less than you and isn't happy to hear you got a raise.
2) has less education than you and doesn't care that you want to go back to school.

If you dated someone like that, what should/would you do?

If someone didn't support my professional life or educational goals, then, no I couldn't be with them. I would end up resentful and hold it against them, even if it is only subconsciously.

Well he just glared at me. And I just shut up and ate my dinner. He told me he was going back to school to get his college degree. I am understanding of the fact that circumstances made it hard to get a degree and I did think it was a good idea and told him so. I was happy as he was with the Navy during the war and he has access to the GI Bill. But when I told him that I planned to go back to school again too, he went quiet.

We dont really have much in common. I dont know why he keeps asking me out and I dont know why I keep saying yes. 😢