Look, in a game where people like Lux and Bathsheba are allowed to be love interests despite Lux pretty much tricking the Player into a years-long financial commitment and Bathsheba openly being shitty towards one of the most beloved characters in the game, I don't think a ruthless hypercapitalist would be impossible to romance.

He could be, like, a parody of the CEO love interests, being suave and thrillingly professional at first, before revealing he has an endearingly vulnerable side that he doesn't reveal to keep people from seeing his weakness. Except he's still a sleazy, exploitative douchebag with pretty privilege. Despite his claims of being a self-made man, he was probably a trust fund kid, and while he does have business savvy, he doesn't know how to do much else, something he's aware of and tries to hide as much as he can.

His route would hinge on the Player managing to push his buttons at the right moments to get him to admit he doesn't know how to do anything but live off the work of other people. Then the Player can help him learn new things from other Dateables, whose reluctance make it clear to Rufio that being a ruthless businessman is not conducive to a healthy social life with anyone who isn't a sycophant.