Sean has a sick fascination with pain mixed with beauty.

Sean was in some form a 'therapist' to many and that can be illustrated in the show that, for a guy like that, he almost never changes his number... so there's a way he had to make a good final impression. But I think he has an abuse fetish and he crosses it with external beauty so he can gauge how much of the pain is he hiding through beauty, and how much of it was preventable by concentrating or focusing on external beauty as a coping and distraction and disarming mechanism for abuse.

He is not trying to put that out on the world but understand it for himself so there's a way that he has to take the abuse on himself to understand it without over-evocation. But as great as some of his stories may be the abuse behind it must be scary. For example when Sheen and Sasha and Austin Green's character all wen to Vegas, I might be getting the exact details wrong but a group of women reverse gang-banged him and I think that was a sports team. Whatever he went through that night, a percentage of it must have been extreme abuse and he is trying to understand it and hide it equally and use that beauty as a coping OR defense mechanism and understand the difference.

Jordan could him as much as any woman could give a man like that but more so than his infidelity his dishonesty concerning his extra-partnership affairs, partially stemming from his limitations dealing with his own shame is the limitation on the strength of their relationship.