Apr 12, 2024 · Matt Dillon began dating Cameron Diaz in 1995 after they met on the set of There's Something About Mary, in which they co-starred. Their on-screen chemistry translated into a real-life relationship, leading them to date for almost three years.

Feb 19, 2021 · The veteran actor, 57, was seen leaving a stationary shop with his Italian girlfriend, Roberta Mastromichele, before they roamed the streets of the Eternal City on Thursday.

Dec 26, 2022 · 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.

May 23, 2024 · Away from the big screen, Matt keeps his personal life out of the spotlight. He was in a three-year romance with Cameron Diaz from 1995 to 1998 but has been dating Italian actress, dancer and...

Oct 28, 2023 · Matt Dillon's romantic history reveals a series of intriguing relationships in Hollywood. In 2006, he found love with Eliza Dushku after being introduced by friends, but their connection was fleeting. That same year, he briefly dated Denise Richards, a romance that garnered significant media attention due to their celebrity status.

Feb 10, 2023 · Though Dillon was dating a few girls, his first proper girlfriend was actress Carole Mallory. The list doesn’t end here. Dillon had dated actress Ellen Barkin, Brooke Shields, and Heather Graham.

Feb 4, 2025 · Roberta Mastromichele came into the limelight once her relationship with Matt Dillon was revealed. Mastromichele and Dillon met in 2013 at a movie event and fell in love with each other.

Aug 2, 1992 · Who is Matt Dillon dating right now? Matt Dillon is currently dating Roberta Mastromichele. These two dated for about three years, then called it quits just after filming "There's Something About Mary" together. Years later Matt admitted their relationship didn't work out because he wasn't ready to settle down.

Matt Dillon’s dating history dates back to his early years in Hollywood. In the 1980s, he was romantically linked to several high-profile actresses, including Brooke Shields and Heather Graham. These relationships garnered attention from the media and helped solidify Matt Dillon’s status as a heartthrob in Hollywood.

Jun 16, 2023 · Though he’s speaking from his Manhattan apartment on this late afternoon in May, he’s soon off to Europe. “My girlfriend [actress Roberta Mastromichele] is Italian and we spend half our time in...