Hi there, I loved the chemistry between Shadow and Sweeney in the show, so I'd love to take it and just add a slash twist to it. An idea I had was maybe your guy is a lot like Sweeney in the show, drinking way too much and maybe even a little bit of a hobo, he owes the Irish for something, so he does jobs for them but his heart isn't really into it.
My guy, Lilian, is not involved with their mob business at all, he's a veterinarian, owns his own clinic. He's basically the good guy. So maybe he sees your guy all drunk on the street (kinda like in that last episode with Sweeney) and offers him a place to stay? And they start from there? I'd like something that would end up more romantic than dramatic but it could be a slow burn line (or not! lol)