I'm not sure about this. I have no problem at all with hat prisoners. But, this guy wasn't in incredible shape, didn't have a great jaw. Unless he was/is very rich and successful or equivalently tall, the people on here would say that, as a bald guy, he doesn't "deserve" (according to society, women etc.) to have a girlfriend. But, on the other hand, he began with her while he had hair and all he had to do was maintain things with her while going bald. This is considerably easier than getting a girlfriend while bald, which may well be impossible. So I think that he should have tried everything in his power to keep things going with her. So I only feel a limited amount of sympathy for this guy. Firstly, at age 24, he had enough hair to get a gf. Secondly, at age 28, he didn't try everything in his power (here that would be shaving it, as per her request) to keep things going with her.
We don't know whether things would have gone differently if he had shaved his head and removed his hat a little, but he ought to have tried it. Doesn't he care more about sticking with her and the two of them being together than avoiding shame, humiliation and potential insecurity if he tried shaving it and removing the hat? She probably asked the same question in a different way when nexting him. "Doesn't he care more about the two of us being together than maintaining his comfortable hat prisoner life?"
We shouldn't judge because we really don't know what would have happened if he had shaved his head and removed his hat. Many women on Youtube have threatened to leave their boyfriend after something like this, and they were usually NW1 or NW2 men who had a nice looking buzzed head. It could have been inevitable.