I have the feeling they're going to get along great, just commiserating on their horrible "home", lol!

Drinking will definitely help him, lower those internal expectations. XD He's from the 40s - he knows what goes on (canonically, he lived/grew up in one of the queerest Brooklyn neighborhoods, which is fantastic), and he's not opposed to the idea... But that's just not what 'respectable' people did, lifestyle-wise. He needs to be taught differently. (It'll help that he's now in a place with no family obligations, and no judging.)