Guy I'm dating jokes about me seeing other people/"cheating"?

Anonymous
We've been going out for a month. Dates one night a week, minimal texting (neither of us are into texting). Haven't talked about exclusivity yet/what we "are." Here's the problem: He often jokes about me seeing other people. Our last date, I was walking fast and he asked, "What's the hurry? Got a hot date to get to?" Later that night, he saw I'd received a long text from a guy and he joked, "Breakup text with your boyfriend?" Then later (joking): "Are you cheating on me?" This was all in the span of one night. He's aware that I have several close male friends and am frequently approached by guys when I'm out, but I'm always honest with him.

Background: He's a poor conversationalist but definitely tries by asking questions and maintaining eye contact. He told me he likes me because I'm always exploring and trying new things, which he says he finds refreshing. Once there was a miscommunication when we were joking and he said, "Sorry for boring you" sarcastically, but in hindsight maybe he's worried about that? He doesn't do much during the week and doesn't hang out with friends. He's vague when he answers questions about what he does in his free time and there have been dates with long silences between conversation (not awkward, but definitely noticeable). He's even said "I have nothing to talk about." I always have crazy stories to share with him about what new things I did during the week, and he's always very curious, but when I try to engage him by asking what he loves/does/etc, he's vague. Even when I think our dates were boring and he won't ask me out again, he'll text me a week later and ask me out to dinner. He hasn't tried to kiss me yet either. I don't understand him.
Guy I'm dating jokes about me seeing other people/"cheating"?
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