You made a lot of great points in this piece, and it's clear to me that your friend ran into two or more sociopaths (I'm talking about his love interest plus the love interest's passive-aggressive smug friend who came to the door; I'm assuming there were more clones of them, within their social circles...) -- if he'd been confiding in me, I'd have given him a bro-hug and kept reminding him that he's better off without her.
But I will pose this question to you: why SHOULD chivalry necessarily be monodirectional? Why can't women be chivalrous toward men, reciprocally? Or why can't men be chivalrous toward other men? Or why can't women be chivalrous toward other women? And where do nonbinary people fit into it all?
The entire notion of all/most men being expected to act one way toward all/most women is quite antiquated, and utterly anti-individualist.