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  2. 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.

    • Natasha Hooper
  3. Aug 28, 2020 · Ciao Bella: Matt Dillon, 56, and his longtime girlfriend Roberta Mastromichele attended the premiere of City of Ghosts at Rome's Timvision Floating Theatre on Thursday. Dillon cut a...

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    • Lisa Mcloughlin
  4. 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.

  5. Actor Matt Dillon, 56, and girlfriend of four years Roberta Mastromichele, 44, walked the red carpet together on Sept. 2 at the 77th Venice Film Festival ahead of the opening ceremony and the red carpet for the screening of Lacci ( The Ties ).

  6. Dec 26, 2022 · 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.

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  7. Sep 2, 2021 · Matt Dillon looked suave in a black suit and bow tie while girlfriend Roberta Mastromichele oozed glamour in a plunging plum gown as they attended The Hand of God's premiere in Venice on...

  8. Jul 24, 2020 · Matt Dillon holds hands with girlfriend Roberta Mastromichele while attending the second day of the Filming Italy Sardegna Festival on Thursday (July 23) at Forte Village Resort in...