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Sean Penn Dating History

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  •  Married
  •  Relationship
  •  "Encounter"
  • 20
    Sean Penn and Leila George
     73      132

    Leila George

     Pisces Pisces
    Sean Penn and Leila George October 2016 - April 2022
    ""She made worldwide headlines this week after she was spotted kissing Oscar winner Sean Penn on a Hawaiian beach on Wednesday. But just who is Leila George, the 24-year-old lover of Oscar winner Penn, 56? The Australian-born blonde is a burgeoning actress with an A-list pedigree, born to Emmy ... [more]
  • 19
    Sean Penn and Minka Kelly
     70      122

    Minka Kelly

     Cancer Cancer
    Sean Penn and Minka Kelly June 2015
    A source confirms to Us that Sean treated Kelly and a couple of friends to a "very pricey meal" at Thomas Keller's elite eatery The French Laundry in Napa, Calif.for her 35th birthday. (TMZ was first to report the outing, with photos of the pair at the restaurant.) The insider says that ... [more]
  • 18
    Sean Penn and Charlize Theron
     137      106
    Sean Penn and Charlize Theron December 2013 - June 2015
    Charlize and Sean started dating in December 2013, they became in engaged in November 2014. they split in June 2015 [more]
  • 17
    Sean Penn and Calu Rivero
     41      63

    Calu Rivero

     Aries Aries
    Sean Penn and Calu Rivero April 2012 RUMOR
    Carla Soledad Rivero (born April 5, 1987), known as Calu and Dignity, is an Argentine actress, model, designer and occasional DJ. [more]
  • 16
    Sean Penn and Shannon Costello
     43      48
    Sean Penn and Shannon Costello July 2011 - 2013
    Sean Penn has a new lady in his life and her name is Shannon Costello. The couple took their romance public at the beginning of July and have been spotted together on the beach in Malibu, at Nobu earlier this month, and dining out in Miami. Costello, initially misidentified by the media as Stacey ... [more]
  • 15
    Garcelle Beauvais and Sean Penn
     54      56

    Garcelle Beauvais

     Sagittarius Sagittarius
    Garcelle Beauvais and Sean Penn June 2011 RUMOR
    Garcelle Beauvais (: born November 26, 1966) is a Haitian–born American actress, reality television personality, author, and former fashion model. She is best known for her roles as Francesca "Fancy" Monroe on The WB television sitcom, The Jamie Foxx Show, which ran from 1996 to 2001, and as Valerie Heywood on the ABC crime drama, NYPD Blue. She also appeared in the 2017 film Spider-Man: Homecoming as Doris Toomes. In 2020 Beauvais became a main cast member of the Bravo reality television series ... [more]
  • 14
    Sean Penn and Scarlett Johansson
     253      77

    Scarlett Johansson

     Scorpio Scorpio
    Sean Penn and Scarlett Johansson February 2011
    People reports in February 2011 that Scarlett Johansson & Sean Penn took a Whirlwind Trip to Mexico: It was a short getaway, but Sean Penn and Scarlett Johansson made the most of it. The pair left on a private jet from Van Nuys airport Tuesday morning, then were spotted having dinner in Cabo San Lucas ... [more]
  • 13
    Sean Penn and Valeria Golino
     90      47

    Valeria Golino

     Libra Libra
    Sean Penn and Valeria Golino January 2011
    "Sean Penn and Valeria Golino enjoy a romantic dinner at dinner filled with plenty of kisses at Dal Bolognese restaurant. Sean met Valeria in 1991 when he directed her in the film 'The Indian Runner'. After dinner Sean and Valeria went to a party at a friend's house with Paolo Sorrentino ... [more]
  • 12
    Sean Penn and Jessica White
     54      58

    Jessica White

     Gemini Gemini
    Sean Penn and Jessica White August 2009 - September 2010
    Jessica White was linked to actor Sean Penn when they were spotted kissing in the fall of 2009, but the two were seen together again in the summer of 2010. No word on how serious they are, but these two are definitely enjoying each other's company. [more]
  • 11
    Sean Penn and Petra Nemcova
     114      51

    Petra Nemcova

     Cancer Cancer
    Sean Penn and Petra Nemcova January 2008
    Less than two months after he announced his separation from his wife of 11 years, Sean Penn hit Sunday night`s Oscar party circuit with a new blonde beauty on his arm: model Petra Nemcova. The two arrived together (or, at least, simultaneously) at the Elton John AIDS Foundation screening party. Although ... [more]
  • 10
    Sean Penn and Elle Macpherson
     52      52

    Elle Macpherson

     Aries Aries
    Sean Penn and Elle Macpherson 1996 RUMOR
    In A Clinch: Sean Penn And Elle Macpherson February 17, 1996|By J. Logan, INQUIRER STAFF WRITER This report contains information from the Associated Press and the New York Post Hot Couple of the Moment alert (and let's hope it's only for a moment): the sullen, chain-smoking pugilist/actor/ ... [more]
  • 9
    Emily Lloyd and Sean Penn
     42      46

    Emily Lloyd

     Libra Libra
    Emily Lloyd and Sean Penn 1995
    "Emily LLoyd: MY NIGHT IN A HOTEL WITH SEAN PENN: "We’d only been shooting Under The Hula Moon for a few days when my co-star Chris Penn, brother of Sean, approached me. ‘My brother has a crush on you,’ he said. Two days later, Sean arrived on set with his two children. He was ... [more]
  • 8
    Robin Wright Penn and Sean Penn
     8694      54

    Robin Wright

     Aries Aries
    Robin Wright Penn and Sean Penn August 1990 - April 2009
    Sean and Robin started dating in the early 1990s and have two children together. They got married in 1996 and separated several times before finalizing their divorce in July 2010. [more]
  • 7
    Jewel and Sean Penn
     210      47


     Gemini Gemini
    Jewel and Sean Penn 1990
    During a separation from Wright in the mid 1990s, Penn dated singer and songwriter Jewel Kilcher. He was also the director of the original video for Kilcher`s hit song "You Were Meant For Me". [more]
  • 6
    Madonna and Sean Penn
     1233      79


     Leo Leo
    Madonna and Sean Penn February 1985 - September 1989
    This couple`s relationship was infamously contentious, with Penn at point being arrested for assaulting a photographer on a film set while married to Madonna. Madonna dedicated her third studio album "True Blue" to Penn, writing in the liner notes that Penn was "the coolest guy in the un ... [more]
  • 5
    Barbara Hershey and Sean Penn
     42      40

    Barbara Hershey

     Aquarius Aquarius
    Barbara Hershey and Sean Penn June 1984
    "Sexy Sean Penn, recently broken up with the beautiful young actress Elizabeth McGovern, consoled himself by showing up to a Los Angeles screening of "The Pope od Greenwich Village" with Barbara Hershey. Barbara was last reported seeing Kevin Kline in New York. Does that make her bi-coastal? ... [more]
  • 4
    Susan Sarandon and Sean Penn
     127      50

    Susan Sarandon

     Libra Libra
    Susan Sarandon and Sean Penn 1984
    Susan Abigail Sarandon (; née Tomalin; born October 4, 1946) is an American actress and activist. She is the recipient of numerous accolades, including an Academy Award, a BAFTA Award, and a Screen Actors Guild Award, and has been nominated for a Daytime Emmy Award, six Primetime Emmy Awards, and nine Golden Globe Awards. In 2002, she was honored with a star on the Hollywood Walk of Fame for her contributions to the film industry. [more]
  • 3
    Elizabeth McGovern and Sean Penn
     65      43

    Elizabeth McGovern

     Cancer Cancer
    Elizabeth McGovern and Sean Penn May 1983 - May 1984
    Elizabeth Lee McGovern (born July 18, 1961) is an American film, television, and theater actor, and musician. She received an Academy Award nomination for her role as Evelyn Nesbit in the 1981 film Ragtime. She is also known for her performance as Cora Crawley, Countess of Grantham, in the British drama series Downton Abbey, for which she has been nominated for an Emmy Award and Golden Globe Award. Her other films include Ordinary People (1980), Once Upon a Time in America (1984), The Handmaid's ... [more]
  • 2
    Sean Penn and Brigitte Nielsen
     53      52

    Brigitte Nielsen

     Cancer Cancer
    Sean Penn and Brigitte Nielsen unknown date
    In her autobiography, Brigitte discusses meeting Sean Penn at Cannes and one night of passion they shared together. "Another night I met Sean Penn and Charles Bronson in a club in Cannes. Sean didn't have classic good looks but there was just something about him. In my pushy way I ended ... [more]
  • 1
    Peggy Trentini and Sean Penn
     26      41

    Peggy Trentini

     Cancer Cancer
    Peggy Trentini and Sean Penn unknown date
    Peggy Trentini, author of Once Upon a Star, discusses her book, her journey as a writer, and self-publishing on Kindle. DAVID WISEHART: What can you tell us about Once Upon a Star? PEGGY TRENTINI: It's a story based on my life as a model/actress in Hollywood. It is a true autobiography that details ... [more]
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