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You can watch My First Mister (2001) for free on Fawesome.

Leelee Sobieski is brash, abrasive and vulnerable as a teenage child of divorce who hides her pain behind a mask of hard-edged gothic rebellion. Albert Brooks plays a man who is her total opposite, a precise and well-ordered menswear store owner of forty-nine who manages limited expectations and protects lonely secrets with pleasant ritual and quiet, ironic reserve. These two total opposites collide in conflict then come together in a surprising alliance, changing each other's lives forever.

My First Mister is a film that explores themes of high school, friends, misfit. It also touches on teenage girl and older man younger woman relationship and rebellious youth.

Trailer