Hey Anon, this is a super weird situation that I’ve never seen before. I’m as stumped as you are about his intentions.
Right off the bat, I’m concerned that he doesn’t want to take you out. Not only is that weird, it’s totally rude and disrespectful. Even if he has no money, he could still plan to take you on fun dates that don’t cost anything like going to the park, or going to a museum. The fact that he insists on only meeting at either of your apartments shows that he’s not trying to put in any effort to win you over, and that would be enough for me to tell this guy to hit the road – which I suggest you should do!
I also don’t understand why he hasn’t put any moves on. He’s respecting your boundaries, which I concede is cool, but it also sounds like he isn’t even kissing you when you hang out? That’s weird. Also, 8 months is a very long time to hang around just to get laid, so I doubt this is about sex for him either. What it IS about, however, I have no idea.
In conclusion, this guy is messing with MY head so lord only knows what he’s doing to you… YES you should 100% ask him what the hell is going on, and free yourself (on way or another) from this dating no mans land.
Then please let us know what he says because this is all so confusing…!