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.
Most Helpful Guy
From a relationship coaches perspective, all of this sounds very much like insecurity on his part. Why do I say that?
1) People who frequently throw out lines about someone they're dating seeing other people or having better options is really just protecting their own insecurities. They question the things that they bring to the table and when they get even a small glimpse that someone else may be at the table, their mind wanders. But they know that it's not healthy and won't be looked upon favorably if they become accusatory and so they throw it out there as a joke.
2) Him not kissing you? He's in constant wonder whether you really like him, what with you getting looks from other guys and the texts--again, his mind wanders.
3) Same goes for the "sorry for boring you"--he constantly feels as though he isn't good enough for you but hides his feelings through subtlety and sarcasm.2
Most Helpful Girl
He's a bit passive aggressive and looking for some reassurances that you're interested in him. He doesn't want to open up too much if you are juggling several guys. He clearly wants to be with you. Hopefully he has SOMETHING going on in his life. You should ask him what he wants, if he's looking for a relationship, what his goals are, I might also suggest not texting other people while on a date with him. just put your phone away.2