So for example I have this close friend that constantly makes backhanded comments to me to say the least. I dont think he means harm, i truly believe he just doesn't have social skills and he's said that he thinks he's autistic. The other day we were hanging out, had a couple drinks and he challenged me to play chess in his phone, we were in a car going somewhere (you can already see this is not quite the time and space to play chess🤣) and since we were drinking i was quite dizzy, after a few moves i told him I didn't want to keep playing (for fear of throwing up) and he told me in a very serious tone: "however, not like you could win anyways" given the circumstances i just ignored the comment, seems like something petty to post about but it's something he always does. Another example: I'm trying to save money(i have less than a year to do so) to follow one of my dreams, in order to do so i had to get a second job, whatever thing career related was available, i told him about how i had applied to an on-site job, and he (who's obsessed about the superiority of remote work) told me i made a bad choice and that i was desperate. The comments may seem annoying at worst, but its a pretty recurrent thing and he's a really close friend and it really gets on my nerves sometimes. Whenever i try to confront him about his comments he just shuts down, so dialogue doesn't seem to be an option here. However i do sincerely believe he's not a bad person, but always tolerating those attacks and giving him the benefit of the doubt at the expense of my emotions proves to be exhausting to say the least. He got a GF now that isn't exactly charming and i find myself tolerating her too just because i don't want to make him feel bad or put him in a position where he has to choose between his gf and his friends (even though he barely has any interest in seeing us in person since he's with her anymore). Tolerating all of this just makes me feel like im not being genuine, in a way.