Does Matt Dillon Have a Wife? The Actor Seems to Have Found Love with Roberta Mastromichele

Matt Dillon once opened up about marriage, and the actor said he was open to the commitment. He dated a few actresses throughout his career, but it wasn't until after he fell deeply in love that he came to that conclusion. A few years ago, he was even rumored to be engaged.

Matt Dillon broke into the acting industry in the 1980s and soon became a heartthrob. The proud New York native, born in February 1964, received much praise for his versatility on the big screen, dabbling in various genres.

Among his most notable credits is the 1998 romantic comedy "There's Something About Mary," where he played an obsessed private investigator named Healy. The multi-award nominated star appeared in another classic that same decade in John McNaughton's "Wild Things."

Matt Dillon is pictured during the Pro-Peace Fundraiser at New York City Palladium on January 18, 1986, in New York City | Source: Getty Images

Dillon also took voice-acting roles, appeared in several series, and later branched into TV and film directing. He's also joined the judging panel at many film festivals over the years. His accomplishments clearly show his passion for cinema, but fans of the actor have also been curious about his love life.

In 2006, Dillon reflected on his place in the world and how his last relationship opened him up emotionally. Following his separation from his previous beau at the time, he felt unsatisfied with himself as a man and his relationships, as he explained:

"I was dissatisfied with where I was as a man, with my relationships, with my career. I thought my career was who I was. It wasn't until later that I discovered I was more than that."

Matt Dillon poses at the Power of Film Gala to Benefit FILMAID at Time Warner Center on October 16, 2006, in New York City | Source: Getty Images

The sentiment came after his career took a brief slump, which led to a decrease in high-profile movie offers despite his talents. Thankfully, he found his feet again and welcomed hope with a grain of salt as he reflected:

"When I look at what has happened to me in the last few years, I have a kind of guarded optimism. And that's what faith is, isn't it? You don't shut the door on hope."

Although Dillon has remained relatively private about his romantic life, he has given love a try a few more times. His most recent relationship, with Roberta Mastromichele, marked its seventh anniversary this year, and the couple was once rumored to be engaged.

Matt Dillon poses at the 75th Locarno Film Festival red carpet on August 4, 2022, in Locarno, Switzerland | Source: Getty Images

Matt Dillon Dated Cameron Diaz, Whom He Called His "Muse"

Dillon and Cameron Diaz met in 1995 when the pair were shooting separate films in the same city, Minnesota. Dillon worked on "Beautiful Girls," while Diaz starred in "Feeling Minnesota." Their romance began in January 1996; however, they initially kept their relationship low-key.

Diaz especially took care not to mention her former flame's name during interviews when they were still new as a couple. By the following year, she was more comfortable talking about Dillon, whom she affectionately referred to as Matty.

Matt Dillon and Cameron Diaz are pictured arriving for a celebrity screening of the movie "Matilda" at an unspecified location and date | Source: Getty Images

During a 1997 chat, Diaz raved about Dillon, describing him as an "intelligent, poetic, full, real human being" whom she loved "incredibly." In 1998, the pair starred in "There's Something About Mary," where other co-stars witnessed their bond on set.

As Lin Shaye recalled, Dillon would give Diaz shoulder rubs after long hours of filming. Explaining how she would notice them sitting on a bench together or "stretching out" while Diaz laid her head on Dillon's chest, Shaye thought:

"They were affectionate in a really gentle way."

Cameron Diaz and Matt Dillon are pictured at the 5th Empire Magazine Film Awards 1997 at the Park Lane Hotel in March 1997, in London, England | Source: Getty Images

Shortly after the movie was released that year, reports of their separation surfaced. Although neither of them spoke about it at the time, especially Diaz, who later married Benji Madden, Dillon was quite frank about their split several years later. When he talked to Rolling Stone in 2006, he said:

"When something isn't happening — look, I loved her, and we were very close, but it just ran its course. We're both actors, she was living in L.A., and I was living in New York, and I didn't want to commit to moving out there."

Matt Dillon and Cameron Diaz pose for photos during arrivals at the 70th Annual Academy Awards ceremony on March 23, 1998, in Los Angeles, California | Source: Getty Images

Dillon added that he didn't want to blame their breakup on his reluctance to move to Los Angeles. He simply acknowledged that the time had come for him and Diaz, who was also once rumored to be engaged to Jared Leto, to go their separate ways. Still, she was the first woman to open him up emotionally, as he reflected:

"It's a very powerful thing when you feel that way about somebody. Cameron was a muse for me."

Cameron Diaz and Matt Dillon are pictured arriving for the premiere of "There's Something About Mary" on July 9, 1998, in Westwood, California | Source: Getty Images

Matt Dillon Was Linked to Some Other Famous Women

In June 2014, Dillon enjoyed dinner with Antonio Banderas' ex-wife, Melanie Griffith, in Rome, during the Taormina Film Festival in Sicily. Two weeks before their meeting, Griffith had filed for divorce from Banderas after 18 years of marriage.

However, it's unknown if the dinner was of a romantic nature. Dillon is also counted among actress Heather Graham's former flames, but their relationship timeline eludes public knowledge.

In 2013, she said every person she had dated was "great," but they weren't a "compatible match." Dillon has also been romantically linked to actresses Brooke Shields and Denise Richards.

Matt Dillon poses on the red carpet for the movie "The Hand Of God" during the 78th Venice International Film Festival on September 2, 2021, in Venice, Italy | Source: Getty Images

Matt Dillon Has Been Dating Italian Actress Roberta Mastromichele for a Long Time

Dillon and Mastromichele started dating in 2014, but the couple made their first public appearance in 2015. They are known to frequent Rome, and their 2017 trip to the Italian capital sparked some engagement gossip.

As Dillon and Mastromichele strolled the streets of Rome, sightseeing in casual attire, Mastromichele notably donned a large diamond ring on her wedding finger. Speculation on whether they planned to wed followed, but neither confirmed nor denied.

Matt Dillon and Roberta Mastromichele pose at the 75th Locarno Film Festival red carpet on August 4, 2022, in Locarno, Switzerland | Source: Getty Images

They returned again to Rome for the 2020 "City of Ghosts" premiere at Timvision Floating Theatre in August 2020. Dillon appeared in a movie of the same name in 2002, which he wrote and directed, and starred alongside James Caan.

His beau is an actress and choreographer who also serves as an additional crew member in the art department. Mastromichele was born in 1976 and is best known for her work in 2010's "The Tourist." Recently, she was involved in 2022's "Questa notte parlami dell'Africa."

Matt Dillon and Roberta Mastromichele are pictured at the 78th Venice International Film Festival 2021 on September 1, 2021, in Venice, Italy | Source: Getty Images

What Is Matt Dillon up to Now?

Dillon grew distant from Hollywood as he felt most of what was made in the industry was "rubbish." He became highly critical of his characters and the scripts proposed, which lessened his chances of being considered for big movie parts.

However, he hasn't entirely stopped acting. Dillon has appeared in B-list movies, Indie films, and TV series such as FOX's "Wayward Pines." Since 2011, he has worked on a documentary – in post-production since May – about Cuban musician Francisco Fellove's legacy. Dillon said it encompassed two of his passions: jazz and cinema.

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