PRobably soon now that Rosanna & Craig did the nasty. I could handle Carly coming back to town with TP and staying with him for awhile instead of Jack. Still car-jacker fan and Jack is knee deep in his own problems with Janet & liberty so it might make sense.
I don't really want him with Allison or Katie, they seem to get all the guys. But it could be going that way, considering Katie is going to (my assumption) break up with brad over the whole abortion thing with Liberty, and Allison seems pretty upset with Casey these days, although Maddie is right there to pick up the pieces.