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In 2005, he starred in the mid-season replacement series The Bedford Diaries.
The producers had only Ventimiglia in mind, but the show lasted only eight episodes and was one of several shows not picked up by the newly formed network The CW.
He has guest starred on such television series as CSI: Crime Scene Investigation, Sabrina, the Teenage Witch, Law and Order: Special Victims Unit and Boston Public.
He had the part of the main character, Jed Perry, in the short-lived Fox TV series, Opposite Sex, which originally aired in 2000.
From 2002 to 2006, Ventimiglia played brooding teen Jess Mariano on Gilmore Girls; he was introduced in the second season as a leading cast member.
He signed on for a spin-off of Gilmore Girls called Windward Circle which was to be focused on the relationship between Jess and his estranged father (played by Rob Estes), but the proposed series never made it to air.
He has made guest appearance in many popular TV series like the Teenage Witch, Law and Order: Special Victims Unit, CSI: Crime Scene Investigation and Sabrina.
Ventimiglia made his debut as party guest #1 on The Fresh Prince of Bel-Air (1995), eventually being cast in the short-lived Fox series Opposite Sex in 2000.He was rumored to be dating beautiful actress Emmy Rossum but the rumor never got officially confirmed.Though he was seen playing the role of gay character in some of TV series he is not gay.Prior to being single, he had dated Gilmore Girls co-star.After dating for three and half years they ended their relationship.