103.2k readers

Sean Penn's Loves & Hookups

Updated June 14, 2019 103.2k views19 items

Who is Sean Penn dating? Who Sean Penn dated; list of Sean Penn loves, ex girlfriends; marriages and breakup rumors. The loves, exes and relationships of Sean Penn, listed by most recent. Now that Sean Penn's no longer has a wife, it'll be interesting to see what Hollywood starlets he links up with. Will he fall for the roster of famous babes that end up in celebrity "tapes?" Not to say anything about Sean Penn, but his celeb tape would probably be something you watch out of curiosity as opposed to it being hot. Who knows if he'll end up on the list of celebrities with such tapes anytime soon...

Which of Sean Penn's exes is the hottest?

  • Photo: Brad Barket / Getty Images

    Sean Penn began dating actress Leila George, daughter of actor Vincent D'Onofrio, in late 2016. 

    Leila George D'Onofrio is the daughter of Vincent D'Onofrio and Greta Scacchi....  more
    • Age: 28
    • Birthplace: Sydney, Australia
    • Gender: Female
  • Photo: Fuzheado / Wikimedia Commons

    Sean Penn started dating Charlize Theron in 2013, but the pair split just over a year later.

    Charlize Theron ( shar-LEEZ THERR-ən; Afrikaans: [ʃarˈlis trɔn]; born 7 August 1975) is a South African and American actress and producer. She is the recipient of several accolades, including an Academy Award, a Golden Globe Award, and the Silver Bear for Best Actress. Time magazine named her one of the 100 most influential people in the world in 2016, and she is one of the world's highest-paid actresses, as of 2019. Theron came to international prominence in the 1990s by playing the leading lady in the Hollywood films The Devil's Advocate (1997), Mighty Joe Young (1998), and The Cider House Rules (1999). In 2003, she received critical acclaim for her portrayal of serial killer Aileen...  more
    • Age: 45
    • Birthplace: Benoni, Gauteng, South Africa
    • Gender: Female

    More Charlize Theron 

    #7 of 274 The Best American Actresses Working Today#29 of 201 The Best Actresses Working Today#73 of 508 The Most Beautiful Women Of 2021, Ranked

  • Photo: Gobierno / Wikimedia Commons

    Rumor has it that Sean Penn linked up with Calu Rivero in 2012.

    • Photo: Sachyn Mital / Wikimedia Commons

      Shannon Costello

      Sean Penn dated Shannon Costello from 2011 - 2013.
      Shannon Costello is a film producer....
      • Gender: Female