The Adventures of Sebastian Cole

The Adventures of Sebastian Cole is a 1998 American comedy-drama film written and directed by Tod Williams and starring Adrian Grenier as the title character.

Plot
In June 1983 in Dutchess County, New York, Sebastian Cole's stepfather, Hank, drops a bomb: he announces that he is having a sex change operation. Sebastian's sister, Jessica, leaves immediately for California, and his mother, Joan, takes him back to England. Eight months later, Sebastian is back in New York, knocking on Hank's door. Hank (now Henrietta) takes Sebastian in and supports him over the next few months of high school. Sebastian's "adventures" are mostly self-destructive.