Someone attending the 2019 Primetime Emmy Awards might never have known Ben Stiller and Christine Taylor had announced their split two years prior. They two actors sidled close to one another and smiled for photos on the purple carpet of the event, and inside the auditorium, Taylor “was smiling and leaning forward and in toward” Stiller, with the duo looking “happy” and never leaving “each others’ sides,” an eyewitness told Us Weekly.
Stiller and Taylor, who married in 2000 and have costarred in many projects together, were also spotted chatting with Paul Dano, Zoe Kazan, Billy Porter and Eugene Levy at the awards show and its afterparties. (Stiller was nominated for two Emmys at the star-studded event — Outstanding Directing for a Limited Series, Movie or Dramatic Special and Outstanding Limited Series — for his work on the Showtime series Escape at Dannemora.)
Indeed, the still-married couple have been spotted out on multiple occasions — with and without their two kids, Ella and Quinn — since revealing their breakup in May 2017. “With tremendous love and respect for each other, and the 18 years we spent together as a couple, we have made the decision to separate,” the Zoolander costars told Us in a joint statement at the time. “Our priority will continue to be raising our children as devoted parents and the closest of friends. We kindly ask that the media respect our privacy at this time.”
Stiller and Taylor met while filming a 1999 TV pilot called Heat Vision and Jack, which never made it to air. And for the Night at the Museum star, it was pretty much love at first sight. “When I met her, I pretty much thought, ‘That’s the person,’” Stiller told Entertainment Tonight in a 2007 interview. “It was like, ‘Wow, this is a great person. I love her.’”
Scroll down for photos and details from the pair’s on-and-off relationship over the past two decades.

The couple tied the knot in an oceanside ceremony in Kauai, Hawaii, on May 13, 2000.
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Taylor played Stiller’s love interest in the male model comedy Zoolander. (They also collaborated on the films DodgeBall: A True Underdog Story, Dedication, Tropic Thunder and Friendsgiving.)
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The couple welcomed their first child, daughter Ella, on April 9, 2002. She later scored roles in three of her dad’s projects: Megamind, Night at the Museum: Secret of the Tomb, and Escape at Dannemora.
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Taylor gave birth to the couple’s son, Quinn, on July 10, 2005, and he also had parts in Megamind and Night at the Museum: Secret of the Tomb, as well as a voice role in Madagascar: Escape 2 Africa.
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The duo announced their separation on May 26, 2017, less than a year after Stiller announced he had secretly battled prostate cancer.
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Taylor and Stiller were spotted laughing and looking convivial as they shared a two-hour lunch in New York City’s Tribeca neighborhood.
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Taylor avoided questions about her and Stiller’s relationship status at a charity event in October 2018, simply telling Us, “We’re a big family. We’re together all the time.”
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The estranged couple were spotted together two nights in a row in late September. On September 21, they attended the 13th Annual Evening Before event in coordination with the Emmys, benefitting the Motion Picture & Television Fund. The next night, the duo stepped out at the 71st Primetime Emmy Awards in Los Angeles together. During the awards show, Taylor “was smiling and leaning forward and in toward” Stiller, an eyewitness told Us at the time. The pair looked “happy” and never left “each others’ sides,” the insider added.
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One month after attending the 2019 Emmy Awards together, Stiller and Taylor reunited at the Project ALS New York City Gala on October 23, with their daughter, Ella. “[Ben and Christine] weren’t hanging out together, only because they knew a lot of people at the event and were chatting and catching up with them. Same with Ella — hugging lots of people,” an eyewitness told Us at the time. “At one point, Ben put his arm on Christine’s shoulder to get her attention. It seemed very natural and organic.”
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On November 18, the two former flames attended Rosie O’Donnell’s RTKids Gala together. At the event, the Zoolander actor was honored for his work in supporting children’s education throughout the world. Their eldest child, Ella, was also there with them.
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Taylor starred in the Thanksgiving holiday film Friendsgiving, which was released in October 2020 and produced by Stiller.
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