I've been dating a guy for about 3 months now. It's been going well and we've gotten closer recently. About a month in, I asked if we were exclusive as I wasn't really interested in casual dating anymore, and he told me to just go out and do whatever and just let him know if it starts getting physical with other men. I didn't go out for awhile, and then recently I decided I should probably start dating other guys if things aren't going to progress.

I think part of his problem is he's a bit older (36 vs. my 23) and he just thinks I'm too young to want to settle down yet, which isn't true. I've done the casual thing for years now and I'm over it. I do agree the age difference is a big factor, but it's caused no real issues so far. He's kind of your typical bachelor and doesn't want kids (I don't either) so it's not like he's going to have to wait another 10 years for children or anything.

Also, he's mentioned he just doesn't think he's good enough for anyone to want him. So clearly he has self-esteem issues he needs to work on. I try to get him to elaborate and try to work through it, but he doesn't like to expand too much. Maybe he's just scared that I won't want him anymore after a little while.

Anyway, I started going on other dates now because I figured if this wasn't progressing, I should start exploring other options. I've been on a few dates with a couple other guys. He usually asks what I'm up to on days that we don't hang out. A couple of weeks ago he asked who I hung out with the night before, and I just said "why do you care?" and he just said "Why do you keep asking why I care. Of course I care." I had made a joking comment about "why do you care?" if other guys hit on me while I'm at the bar. He mentioned he hasn't been seeing anyone else really and I just said "you can't be upset with me since you literally told me to go out and do whatever I want when I asked if you wanted to be exclusive." He said he definitely wasn't mad or anything, and then just went on his insecurity spiel again. I just didn't know what to say. We stopped talking about it and things are back to normal, but like I just don't know.

He clearly has issues he needs to deal with before getting into a relationship. He's the first guy I've really liked in a long time, though. He does treat me really well and we have lots in common so I don't want to give up just yet. Don't know how to handle this, though!