Should I ask him our or should I let him go?

He's shy, I'm shy. We met once a week for intramurals. It started with him driving me home, smiling and looking at me, and coming up to me and saying hi or attempt to have a conversation. Few weeks of that continues, next we're at a party... both tipsy and he kissed me. We made out, then i broke it off bc i wasn't sure if he actually liked me. He continues acting the same, but i got really awkward/quiet around him bc he never talked to me outside of when we saw each other. I'd text him, we'd talk, and he'd stop replying but he isn't much of a texter to begin with.

We went skating with our friends, that was also awkward since i basically avoided eye contact and didn't talk when we ate.. but when we went skating that wasn't too bad and we did talk a bit. A month goes by, no contact. Then two weeks ago, he texts me saying that it's been a while, and another one saying he thought of me and suggested we hang out soon.

I'm just unsure because this has been going on since October.. and he'll have moments where he's bold (kissed me, texts me saying he thought of me) and then he's shy or i won't hear from him. We don't talk a lot, and i dont really know what to do since i feel shy/awkward.
Should I ask him our or should I let him go?
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