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Matthew Raymond Dillon, an American actor and film director, rose to prominence in the late 1970s and 1980s. Born on February 18, 1964, he earned recognition for roles in iconic films such as Drugstore Cowboy and later, the comedy hit There’s Something About Mary, both of which solidified his status as a household name. His performances garnered critical acclaim and led to numerous award nominations during the peak of his career.
Commonly referred to as Matt Dillon, he has been linked to several high-profile relationships over the years. One of his earliest reported relationships was with actress Carole Mallory, although the timeline of their involvement remains speculative, likely occurring in the 1970s. He was later romantically associated with adult film actress Seka, who was approximately ten years his senior, not younger as commonly misreported. Their relationship was brief.
Dillon also dated Karen Campbell for a short period, though details about their relationship remain limited. He was rumored to have had brief connections with television personality Sonja Morgan and actress Ellison Jordana, although these claims were largely dismissed as speculation and never verified by credible sources.
One of Dillon’s more prominent relationships was with actress Ellen Barkin. Though brief, their relationship attracted significant media attention. In the early 1980s, he also dated Brooke Shields for approximately a year, from 1980 to 1981. Following this, he entered into a relationship with actress Heather Graham in 1988, which also lasted about a year.
Perhaps his most well-known relationship was with actress Cameron Diaz. The two met during the filming of There’s Something About Mary and became a high-profile couple. Their relationship was heavily covered by the media and reportedly marked Diaz's first serious romantic involvement in the public eye. Despite widespread rumors of an upcoming marriage, they ended their relationship shortly after the movie's release in 1998.
Following the end of his relationship with Diaz, Dillon briefly stepped away from high-profile acting roles. The emotional toll of the breakup reportedly impacted his career trajectory, as his appearances shifted more toward smaller, less visible projects. However, he experienced a significant resurgence in 2004 with his performance in the critically acclaimed film Crash. His role earned him an Academy Award nomination for Best Supporting Actor, effectively placing him back in the industry spotlight.
Post-Crash, Dillon continued to work in film and television, albeit with more selective roles. In the years following, he was rumored to be romantically linked to actresses Eliza Dushku in 2006 and Hallie Eisenberg in 2009. However, these reports were largely speculative and received minimal attention from reliable media outlets.
As of recent reports, Dillon has been in a steady relationship with Italian choreographer Roberta Mastromichele. The couple has maintained a relatively low profile, favoring privacy over public display. Despite several relationships throughout his life, Dillon has never been married and thus has never experienced a divorce.
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