Im confused by the progression of events between me and him?

[Anonymous]

so this is a gist of what has happened the last 3 weeks worth of conversations between me and my friends with benefits:

week 1: multiple comments from him about me not being okay with our situation (when i joked about our situation before he accused me of not being okay with our situation and hell randomly bring it up at times after conversations)

week 2: for about 30 minutes, he kept asking me how he compared to other guys i have been with (he knows i haven't been with many at all). i told him that it didn't matter due to us enjoying time with each other so why does it matter. he kept saying he just wanted to know where he compared. i tried to stop the conversation by saying that i dont remember some of them due to it being years and he said for me to rank him compared to the ones i do remember.

week 3: we joked about us having a kid (as we do sometimes we both joke about it) due to me having anxiety and him having adhd. i made a comment about me dropping off the kid at his place and we joked about that. then he started saying how he doesn't see us living together as working due to us being incredibly alike and similar (in some ways we are but i dont think we are that similar). he said that he feels like we would argue a lot and that wouldn't be good for the kids to be around. i joked saying it would just add spice to life and he kept saying the same thing.

*i am just confused by the progression of conversations. usually whenever i joke about our situation or our friendship (such as he always buys me food to make sure im fed, i offer to give him money back, and hell say that we both know how i can repay him, etc- light hearted jokes) he would accuse me of not being okay with our situation. i told him multiple times that i have never said that and if i felt that way that i would explicitly say that.

also another conversation that happened last night was that a coworker was hitting on me and he found out and he looked like the definition of someone just very meh.

Updates

2 d

also whenever we hangout i guess he assumes im staying the night because a few times now after we hook up or finish a movie, ill be like okay im going home and hell seem surprised that im leaving. and he'll want me to pick out where we eat or hell surprise me with starbucks or he''ll let me pick out the movie.

[HollyK21]

I think this is about him protecting his boundaries, and doing his best to assert them whenever there’s even the slightest idea of actually getting serious. You are doing your best to play your role, and trying to assure him that you don’t want more. Yet I can’t help but feel as though you’re stifling your own feelings as to keep this going, and once you really start recognizing that, things will inevitably change. Why? Because you’re a human, not a robot. You can’t share your body with some time after time and expect no deeper feelings to form. You’re just dealing with a guy who doesn’t want that, and you should be more honest with yourself about whether or not the casualty of this situation can really work long term. Eventually you’ll start asking yourself if you can continue to rob yourself of a true connection and real direction all for this dude who doesn’t want more. If you haven’t had those thoughts already.

[WhitneySnow]

He doesn’t want to date you! He likes hooking up with you and just wants to make sure you feel the same way and you’re not expecting anything more (which I think you are or you wouldn’t have asked this question).

[WhitneySnow]

He wants to have sex all night