A strangely erratic character he first dismisses Francine but then lusts after her when she looses her toga at the school play.
They date for a year but Francine doesn't want sex with him until it feels right. Eventually he gives her up and has a string of affairs but never looses his love of Francine. The breakup gives Francine a mini breakdown and she strips in a park before him and drives home naked and crashes the car in a daze. Katchoo incensed takes a butch female friend round to Freddie's and threatens him with a gun before ting him up naked in a store front window.
Ever since his relationship with Katchoo has been hostile but limited to just snipes and words.
After an art show of Katchoo's works based on Francie he steals the paintings and his infatuation with his ex grows. He ignores his wife and peruses Francine but to no avail. His marriage to Casey breaks down and they go their separate ways.
Being a Lawyer he reads David's will and reads the letters to his friends as instructed. At the reading he finds his wife Casey was a plan by Tambi.