I’m about to end a situation which has turned into a bit of a head scratcher and thought I’d ask for objective opinions here in case I’m misreading anything. I’m a 41F, he’s 39. On our first date he told me he was insecure. I didn’t think too much of it but we’ve been dating for 6 weeks and his behavior is really confusing me.
In person he is really great. We get on like a house on fire. Outside of that, I feel unsure of his motivations. On a few occasions (particularly when he’s been drinking) he has questioned my level of interest. As soon as I give him reassurance, he responds with something like: “ok cool” or “good to know” then he will be a bit dry/distant over text, as if he’s embarrassed that he’s been vulnerable. Or there was one occasion where he again presumed I wasn’t interested and he sent a dramatic text saying: “ok bye” then an hour later messaged to say he missed me. He can be needy at times e.g. he had a stressful day at work and a few days later he asked why I hadn’t called him to offer support, despite the fact he doesn’t do anything like that for me. When we’ve been on dates, he’s pointed out good looking guys and asked if I find them attractive as he thinks he’s not my type but he also disclosed that he fancies his best friend’s wife and that she likes him too, which just seems like a weird thing to bring up. I’m going on vacation soon and he made a point of saying (jokingly) he doesn’t want me to sleep with anyone while I’m away yet neither of us has brought up exclusivity yet. There’s just a lot of mixed messages.
I’ve tried to talk to him about this but he gets defensive. He can be very complimentary and affectionate but it’s not consistent. What adds to the confusion is that he consistently arranged dates before we slept together and since then, he’s defaulted to more last minute plans which has also given me pause as it makes me feel like I’m an option/that he only sees this as casual. Am I missing something here? This is my first foray into dating since getting divorced so I’m a bit rusty.