- Tim grew up in Toronto, Canada, but always felt more at home in the U.S Lucky that his father was an American citizen, as this allowed Masterson to, at different times, pursue his passions of acting and writing in Los Angeles and New York.
- Taught tennis in French at Club Med in the French West Indies, Guadalupe, for a season in his twenties. Then ventured to Paris and England to look up many of the clients he taught at the club.
- Attended the Toronto High School for the Performing Arts and later Claude Watson School for the Arts.
- Moved to Los Angeles in 1990 and began taking acting classes with coach Lynette Katselas, daughter of famed director Milton Katselas, at the Odyssey Theater.
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