Therapist said he envies me

I really don't understand this. I'm not in therapy to be envied or glorified by my therapist, because now I feel pressured to uphold this weird image he has of me and "envies." He said this after I told him I asked for a girl's number and got it. He also said he envies me when I was talking about how I really liked the visuals of a music video (Heart Shaped Box by Nirvana for context) which I still really don't understand what he was saying he envied in that scenario. There's also this really weird dynamic because I'm a 19yo minority and really into Hip-Hop and the culture/fashion of it and even make some music of my own, and he's a mid thirties caucasian (and there's nothing wrong with that) but he sometimes downplays himself as a "basic corny white man" or thinks I'm from the hood (I'm not) or "cooler" than him in some way. It's just really strange and uncomfortable. Aside from this aspect of our relationship, I've been seeing him for over a year now and things have been pretty rocky with him misunderstanding me pretty often and not doing too great as a therapist, with us making basically no progress since the beginning (this also has been his first year as an official therapist). I'm just really frustrated and am basically emotionally detached from our sessions now. I have way more details if you want context but I just want y'all's opinion on this "envy" or if you've experienced something like this before.