Could I ask for headcanons on how Joker would court someone?

shitsuji-hcs:

Eden: More courting headcanons? I hope you don’t mind me answering this one!

• As he travels so often, time snaps at his heels – and Joker is very aware of that. He won’t spend time chasing after someone who he’ll only ever see once. But, if they were a member of the Circus or even just a member of the audience who happened to watch their performances every so often, then maybe he’d give that relationship a chance.
• God forbid his own circumstances come to light. The thought of getting rid, no, leaving his partner strikes fear through him. Not even getting captured by the Yard matters to him, he just doesn’t want his partner to get involved in such a thing. Joker knows how wrong what he does is, but it doesn’t mean that he’ll willingly divulge a secret to his partner.
• He can’t offer much. Not like the rich men who can seemingly throw away as many wads of cash as it takes to court someone. Though conscious of how he can’t afford lavish gifts, he can still conjure quite a surprise with flowers that sprout from his cane or – if the person he’s trying for allows him to – he’ll dedicate the whole show to them.
• The man’s quite conscious of himself. For one thing, they’d most likely only ever see his stage persona, so what would they think of him without the makeup and hair extensions? The loathing he may feel about his own body – but of course, he has to convince himself that if they would truly love him, it’d be for all of him.
• Joker doesn’t see himself as much of a romantic at all… meaning that he asks absolutely anyone and everyone who’d be willing to help. Peter and Wendy think at first that it’s a right joke that he’d come to them and Doll pretty much only taunts him for coming to a kid about it. Somehow only Emily is willing to help… and he doesn’t feel too comfortable talking to a milksnake about romance.
• It comes to a point where everyone decides to force him out on one of their free evenings to “chase after his beloved”, as Doll gushingly put it. Not that Joker knows how to take someone out for the evening, let alone if it’s appropriate to suddenly call for someone so suddenly, but if he’s shooed out then he really doesn’t have much of a choice.
• He’s well aware that taking someone out for the night would be considered ‘extremely discourteous’, as rich blokes seem to put it, but it is the only time he has for them. Even worse so, all he can provide for them is rounds of drinks at a music hall. Obviously not the most refined of adventures, but he supposes it wouldn’t be true of him to be so posh anyways.
• Joker admits all of his shortcomings in a night to them. Honestly far too quickly for someone to tell a newly found, or possible, partner. Though, if they wanted to have him for who he is, he’d readily set them up on a best of a throne that he can.