Stiller and Taylor, who married in 2000 and have costarred in many projects together, announced their split in 2017. Two years later, they made waves at the 2019 Primetime Emmy Awards as they smiled for photos on the purple carpet. The duo were also seen looking “happy” and never leaving “each others’ sides,” an eyewitness told Us Weekly at the time.
At the same Hollywood night out, they were 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.)
The Emmys marked one of many occasions that the twosome attended together after 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.’”
Taylor and Stiller remained tight-lipped about their relationship status in recent years. She notably dodged a question about whether they were officially back together in October 2018, exclusively telling Us at the time, “We’re a big family. We’re together all the time.” When pressed about her seemingly “nice” post-split relationship with Stiller, the Search Party star responded, “It’s wonderful, it’s wonderful.”
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The pair continued to work together and have kept a low profile while coparenting their kids — Ella and Quinn. In February 2022, however, they confirmed they are back on.
Scroll down for photos and details from the pair’s on-and-off relationship over the past two decades: