Ben Stiller and Christine Taylor: A Timeline of Their Relationship

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Ben Stiller and Christine Taylor: A Timeline of Their Relationship

Plot twist! Ben Stiller and Christine Taylor's love story may not be perfect, but it seemingly has a happy ending. 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.” [sendtonews type="float" key="MTB1lh3CI2-2834206-14453"] 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.” 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:

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May 2000

The couple tied the knot in an oceanside ceremony in Kauai, Hawaii, on May 13, 2000.

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September 2001

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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April 2002

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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July 2005

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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May 2017

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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June 2017

A couple of weeks after the news of their split, Stiller and Taylor appeared in an Omaze video in which they reprise their DodgeBall characters, fitness guru White Goodman and attorney Kate Veatch.

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July 2018

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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October 2018

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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September 2019

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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October 2019

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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November 2019

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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October 2020

Taylor starred in the Thanksgiving holiday film Friendsgiving, which was released in October 2020 and produced by Stiller.

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February 2022

Stiller revealed to Esquire that the pair are officially back together after he moved home amid the coronavirus pandemic.

“We were separated and got back together and we’re happy about that. It’s been really wonderful for all of us. Unexpected, and one of the things that came out of the pandemic,” he said.

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March 2022

After Stiller confirmed the duo's reunion, a source told Us that their previous split was "a serious eye-opener" for the actor. “He missed [Christine] terribly and hated the idea of their kids growing up in a broken home,” the insider added, noting that Stiller realized “what he’d lost” after the breakup.

During the coronavirus pandemic, the Reality Bites director made time for "a lot of self-evaluation" that helped him rekindle his romance with Taylor. “He made a conscious effort to stop sweating the small stuff and figure out how to channel his energy whilst compromising with Christine on those issues that really didn’t matter at the end of the day," the source told Us.

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March 2022

The twosome were all smiles as they attended the BNP Paribas Open tennis tournament in Indian Wells, California. The Meet the Parents star and the Wedding Singer actress “looked very happy together,” an eyewitness exclusively told Us of the outing. “He had his arm around her when they walked in [and they] were sharing a lot of laughs and were very animated during the match.”

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August 2022

The twosome were spotted enjoying the U.S. Open at the Billie Jean King National Tennis Center in New York City.

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November 2022

Back on — and back out! Stiller and Taylor attended the opening night of Broadway's The Old Man & The Pool and hit the red carpet beforehand.

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November 2022

Stiller and Taylor attended a post-Thanksgiving Knicks game in New York City. There were seated court-side next to Pete Davidson and Emily Ratajkowski.

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January 2023

The duo opened up about their relationship's casual beginnings.

“We were both each other’s, I would say, like, sort of rebound relationship a little bit,” Taylor revealed during an episode of her podcast “Hey Dude … The 90s Called!” on which her husband made a guest appearance.

The Secret Life of Walter Mitty star chimed in: "We weren't taking it seriously." Stiller went on to explain that he invited his future wife to "come hang out" in New York while he filmed the 2000 romantic comedy Keeping the Faith.

"I ended up going and staying the entire summer," Taylor said.

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February 2023

Stiller and Taylor both wore black ensembles as they stepped out at the 75th annual Directors Guild of America Awards in Los Angeles.

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March 2023

Taylor opened up about her and Stiller's reconciliation during an interview on The Drew Barrymore Show. "Family was always a priority, but I think Ben and I both started to grow in different directions," the Search Party alum explained, recalling what led to their split. "And when we made the decision to separate, it was not something we wanted to talk publicly about or took lightly. We were at this impasse of, 'Let's figure this out, what's best at this chapter in our lives.' That's going back three or four years." 

During the pandemic, their uninterrupted time at home helped them get back on the same page. "We all ended up in our house together with two teenagers and we found this way back," Taylor explained. "We had so much time to talk, there were no other distractions. ... It just happened organically." 

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October 2023

Stiller and Taylor made a rare red carpet appearance with son Quinlin at the Project ALS 25th Anniversary gala celebration in New York City. The twosome cohosted the event, with Taylor telling Entertainment Tonight that they planned to be a “team” on stage. “We yin and we yang,” she quipped.