phillys His three year old's nanny, who is basically magic when it comes to handling both Gigi and Jacob.
His deceased wife's sister*. I would kind of die for a Katie Holmes for the sister-in-law, mostly because I'm using Suri Cruise ('09) for his daughter's face. She's pretty special to both Jacob and Gigi.
I would adore a neighbor family (straight or gay) that sort of adopted Jacob and Gigi into the fold, since he doesn't have a relationship with his own family of origin and is a single father.
A fellow writer that he had sort of a messy fling with about six months ago - she'd be between 30 and 40.