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    • Reese WitherspoonReese Witherspoon
      1999 - 2007
  1. Nov 17, 2020 · Ryan Phillippe has not remarried since his 2007 split from Reese Witherspoon, but he has had two children with different women. He also faced legal troubles with his ex-fiancée and ex-girlfriend over allegations of harassment and assault.

    • Reese Witherspoon and Ryan Phillippe Meet at A Birthday Party
    • Reese Witherspoon and Ryan Phillippe Get Engaged
    • March 1999: Reese Witherspoon and Ryan Phillippe Star in Cruel Intentions
    • June 1999: Reese Witherspoon and Ryan Phillippe Get Married
    • September 9, 1999: Reese Witherspoon and Ryan Phillippe Welcome Their First Baby
    • August 2002: Ryan Phillippe Says He and Reese Witherspoon Are in Couples Therapy
    • October 23, 2003: Reese Witherspoon and Ryan Phillippe Welcome Their Second Baby
    • December 19, 2014: Reese Witherspoon Discusses Her Divorce from Ryan Phillippe
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    Although it is widely believed that Witherspoon and Phillippe met on the set of Cruel Intentions, the two had been quietly dating for a bit before they even started filming the movie. During a 1998 interview with Janemagazine, Witherspoon said they met at her 21st birthday party. "I don't know what came over me — maybe the seven Midori sours — but ...

    It didn't take long for Witherspoon and Phillippe to take things to the next level. The couple got engaged about a year after meeting.

    Witherspoon and Phillippe starred in Cruel Intentions alongside Sarah Michelle Gellar and Selma Blair. The film came out in theaters in March 1999 and helped catapult both Witherspoon and Phillippe's careers. In a 2019 interview with Entertainment Weekly, Witherspoon admitted that she had to be talked into taking the role of Annette in the film. "W...

    The couple got married only a few weeks after Cruel Intentionscame out. They tied the knot in Charleston, South Carolina at the Old Wide Awake Plantation along the Stono River. At the time, Witherspoon was several months pregnant with their daughter, Ava.

    Just three months after their wedding, Witherspoon gave birth to their first child, a daughter named Ava. The Big Little Lies star was just 23 years old at the time. She later spoke about being a young mother during an appearance on The Drew Barrymore Show. "To be completely candid, I was terrified too," she said. "I got pregnant when I was 22 year...

    Phillippe told New York's Daily Newsthat the pair were putting in the work with their marriage and attending couples therapy. "The biggest mistake," he said, "is not doing that, ignoring it and having the marriage fall apart because of laziness." Around the same time, Witherspoon also opened up to PEOPLE about their relationship, saying, "I'm not i...

    About four years after having their daughter, the couple welcomed their second child, a son named Deacon.

    During an interview with CBS' 60 Minutes, Witherspoon opened up about her divorce from Phillippe and shared how hard the time period was. "Phew, that was a tough year that followed. I got divorced the next year and I spent a few years just trying to feel better," she said. She went on to say that the struggles she experienced in her personal life a...

    A look back at the '90s power couple's marriage, divorce and co-parenting journey. From meeting at a birthday party to starring in Cruel Intentions, here are the milestones of their relationship.

  2. Apr 16, 2023 · Reese Witherspoon and her ex Ryan Phillippe reunited after she announced her divorce from Jim Toth. 6 The former couple were both on hand to celebrate their son Deacon’s new album.

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    • Emily Selleck
    • Sophie Dodd
    • Ava Elizabeth Phillippe, 24. Phillippe officially became a dad when he and Witherspoon welcomed their first child together, daughter Ava Elizabeth Phillippe, on Sept.
    • Deacon Reese Phillippe, 20. Phillippe's son, Deacon Reese Phillippe, was born on Oct. 23, 2003, in Los Angeles. Now 20, the budding musician graduated from high school in spring 2022, which his parents celebrated with a backyard commencement ceremony.
    • Kai Knapp, 12. Phillippe welcomed his youngest child, a daughter named Kailani Merizalde Phillippe Knapp, with ex-girlfriend Alexis Knapp on July 1, 2011.
  3. Phillippe began dating model and actress Alexis Knapp in May 2010; they ended their relationship in September that same year. After their breakup, Knapp discovered that she was pregnant by Phillippe and gave birth to a daughter in 2011.

  4. Sep 28, 2017 · Reese Witherspoon Talks Getting Married at Age 23 to Ryan Phillippe: ‘I Would Never Change Anything’ Reese Witherspoon Has 'No Regrets' About Marrying Ryan Phillippe at 23 -- Here's Why

  5. Ryan Phillippe’s Dating History: Reese Witherspoon, Rihanna, Amanda Seyfried, More. By Kat Pettibone. May 25, 2023. 10. Shutterstock (4) Ryan Phillippe has had his fair share of...

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