Yep, I've been saying for a long time that Josy is going to swoop in and snatch Jill if MC isn't careful with both of them. The very moment I saw J&J together for the first time in the library, I was like...
well that's it, Josy is going to cuck me. Why else would DPC make the two of them immediate BFFs? Out of all the potential pairings, DPC just happens to bring together outgoing bisexual Josy and timid Jill who is an equal opportunity sleep humper. Yes sir. All Josy has to do is jettison Maya and it's on.
There is no one in the game who is capable of resisting Josy if she decides she wants to visit pleasure town. J&J would be the perfect way for DPC to give an MC rejected Jill another PDA filled relationship w/o having to worry about players crying about the three letters from another dude. I still think Rusty and Jill could happen if you ditch Jill, but DPC is unlikely to actually show Rusty balls deep. He will have no such reservations in showing J&J smashing vag, however.
Also, that outfit is Jill's best.