I was reading your Ragdoll HC’s and ngl there’s something funny about the idea of an AU where he and Jervis got together mostly because just imagining Jervis dealing with a man who probably coils himself around him like a friggin snake in the night and hides in his hats on a daily basis while becoming a flustered mess and some of his... uh... more flexible suggestions.
It’s funny you say this, because the stuff you’re mentioning is also why I kind of also got into the idea of shipping Jervis with TB!Penguin as well. Just the notion of somebody as polite and put together with somebody a lot less refined and disturbing/perverted. Except, like you said, with Ragdoll there is an extra level of freaky from the man.
I think the only thing to consider would be... what would they even talk about? I think Hatter tends to be someone who likes a good story-- so even if the two don’t have more intellectual pursuits between them, I can see Jervis being beguiled by tales of Ragdoll’s travels and what it was like growing up in the circus. I can also see it becoming a game of Ragdoll going between lies and truths, just to see if Jervis is ever able to figure out which is which.
And, naturally, I think Ragdoll enjoys being able to toy and fluster the man.
I think the one thing to make the ship work outside of comedy and actually make it something with a bit more heart, would be to allow Ragdoll to have more wind down moments. And also put an emphasis on his childhood being filled with neglect and only being seen as a way for his father’s circus to make money. So while most of what he does is attention seeking, there is also a vulnerability of having somebody genuinely care about him and not knowing what to do with it.