The Adventures of Sebastian Cole
Hank (Clark Gregg) marries the divorced Joan (Margaret Colin), who's the mother of teens Sebastian (Adrian Grenier) and Jessica (Marni Lustig). But after living with his new family for years, Hank suddenly announces that he's getting a sex change operation. The family then deserts Hank, with Jessica going her own way and Sebastian staying with his mom. But Joan becomes an alcoholic, so Sebastian moves back in with Hank -- now Henrietta -- who turns out to be far more supportive than anyone else.