All he asks me about is what I had for dinner. What is going on?

I try communicating to him my needs but how much effort could you put in before you get tired of teaching him how to be an ideal boyfriend?

Edit: to elaborate:

I'm 27. He's 30. Dating for 4 months.

I've talked to him about not liking my dead-end job and that I want to go back to school. He doesn't ask me to elaborate. I told him I'm I decided not to apply to a program that I've been working on an application for. He said "better to find out now than later." And that's it. I want him to ask me why not. I later told him that I what I really want is to do medical school. He says "wow!" That's it. Doesn't ask me why. I want him to be interested in my hopes and dreams and goals.

By teaching him, I mean communicating to him my needs. Like instead of being upset that he doesn't talk to me about deeper topics, I can let him know that's what I want to talk about. But how do I go about saying, "hey, it'd make me feel more important and cared for if you proactively showed interest in getting to know me inside out. "