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 stepmother, who formerly went by Hank and presented as male, outs herself and announces that she 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 the United States, knocking on his stepmother's door. Now named Henrietta, she takes Sebastian in and supports him over the next few months of high school. Sebastian's "adventures" are mostly self-destructive.