The Journey of Love Between Ben Stiller and Christine Taylor: A Comprehensive Timeline

Plot twist! Ben Stiller and Christine Taylor's love story, while not without imperfections, appears to have a joyful conclusion. The couple, who tied the knot in 2000 and frequently collaborated on various projects, publicly revealed their separation in 2017. However, two years later, at the 2019 Primetime Emmy Awards, they surprised everyone by radiating happiness while posing for photographs on the vibrant purple carpet. An eyewitness informed We magazine that the pair seemed content and inseparable, always by each other's side.

At the same Hollywood night out, Ben Stiller and Christine Taylor were seen chatting with Paul Dano, Zoe Kazan, Billy Porter, and Eugene Levy at the awards show and its afterparties. Stiller, who 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, attended the Emmys alongside Taylor. This marked one of the many occasions that the couple attended together following their breakup announcement in May 2017. In a joint statement, the Zoolander costars expressed their immense love and respect for each other, as well as their decision to separate after 18 years together. They emphasized their commitment to raising their children as dedicated parents and remaining close friends, while also requesting privacy from the media during this time.

Stiller and Taylor first met during the filming of Heat Vision and Jack, a TV pilot from 1999 that never aired. For Stiller, it was love at first sight. In a 2007 interview with Entertainment Tonight, he expressed his immediate connection with Taylor, describing her as a wonderful person whom he loved.

In recent times, Taylor and Stiller have been secretive about the status of their relationship. Taylor avoided addressing whether they were officially back together in October 2018, instead emphasizing that they are a close-knit family who spend a lot of time together. When asked about their amicable post-breakup relationship, Taylor responded positively, describing it as wonderful.

The couple has maintained a discreet lifestyle while co-parenting their children, Ella and Quinn. However, in February 2022, they publicly announced their reconciliation. Keep scrolling for a closer look at their relationship's ups and downs over the last twenty years, along with accompanying photos and details.

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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 wed in 2000 and have acted together in numerous projects, announced their separation in 2017. Creating a stir at the 2019 Primetime Emmy Awards, the couple posed for photos on the purple carpet, radiating happiness and rarely leaving each other's side, according to an eyewitness. They were also seen socializing with Paul Dano, Zoe Kazan, Billy Porter, and Eugene Levy at the awards show and its afterparties. (Stiller received two Emmy nominations at the prestigious event; one for Outstanding Directing for a Limited Series, Movie, or Dramatic Special, and one for Outstanding Limited Series for his work on the Showtime series Escape at Dannemora.)

After publicly announcing their split in May 2017, the couple attended various events together, including the Emmys. In a joint statement, the Zoolander costars expressed their immense love and respect for each other, acknowledging the 18 years they spent as a couple. Despite their separation, their top priority remained their children, as they aimed to co-parent and maintain a close friendship. The couple kindly requested privacy from the media during this time.

Stiller and Taylor crossed paths while working on a TV pilot titled Heat Vision and Jack in 1999. Unfortunately, the pilot never saw the light of day. Stiller instantly fell in love with Taylor when they first met, describing her as an amazing person.

In recent years, Taylor and Stiller have chosen to keep their relationship status private. In October 2018, Taylor avoided answering a question about whether they were officially back together, instead emphasizing that they are a close-knit family and spend a lot of time together. When asked about her amicable relationship with Stiller following their split, Taylor simply replied, "It's wonderful."

Scroll down for photos and details chronicling the pair's on-and-off relationship over the past two decades as they continued to collaborate and quietly raise their children, Ella and Quinn. However, in February 2022, they officially announced their reconciliation.

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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 starred opposite Stiller in the hilarious male model comedy Zoolander. (They also teamed up for the films DodgeBall: A True Underdog Story, Dedication, Tropic Thunder, and Friendsgiving.)

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April 2002

On April 9, 2002, the couple joyfully celebrated the arrival of their first child, a beautiful baby girl named Ella. As she grew older, Ella had the incredible opportunity to participate in three of her father's remarkable ventures: Megamind, Night at the Museum: Secret of the Tomb, and Escape at Dannemora.

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July 2005

On July 10, 2005, Quinn, the son of the couple, was born to Taylor. Additionally, Taylor had roles in Megamind and Night at the Museum: Secret of the Tomb, and also provided a voice 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

Shortly after their separation was made public, Stiller and Taylor made a surprise appearance in an Omaze video, reprising their roles as the iconic characters from DodgeBall – the charismatic fitness expert White Goodman and the diligent lawyer 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

When asked about her and Stiller’s relationship status during a charity event in October 2018, Taylor refrained from answering the questions directly. Instead, she emphasized the closeness of their bond, stating, “We are a tightly knit family. We spend a significant amount of time together.”

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September 2019

The estranged couple were seen together on consecutive nights in late September. They first attended the 13th Annual Evening Before event in support of the Emmys, which benefited the Motion Picture & Television Fund on September 21. The following night, they made a joint appearance at the 71st Primetime Emmy Awards in Los Angeles. According to an eyewitness at the awards show, Taylor was seen smiling and leaning towards Stiller. The pair seemed content and stayed close to each other throughout the event, as reported by an insider.

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October 2019

Following their joint appearance at the 2019 Emmy Awards, Stiller and Taylor came together once again at the Project ALS New York City Gala on October 23, accompanied by their daughter, Ella. According to an eyewitness, Ben and Christine were not seen hanging out exclusively with each other, as they were busy socializing and reconnecting with numerous acquaintances at the event. Similarly, Ella was observed embracing many people. During the festivities, at one point, Ben gently placed his arm on Christine's shoulder to get her attention, creating a sense of ease and naturalness between them.

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November 2019

Both former partners were present at Rosie O’Donnell’s RTKids Gala on November 18. The gala aimed to recognize and appreciate the efforts of the Zoolander actor in advocating for children’s education on a global scale. Alongside them, their first-born child, Ella, graced the event as well.

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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

According to Stiller's revelation to Esquire, he and his partner have reconciled following his return home during the COVID-19 pandemic. "We were separated and got back together and we're delighted about it. It has been truly delightful for all of us, an unexpected outcome of the pandemic," he shared.

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March 2022

According to a source, Stiller's reunion with Christine after their previous breakup was a significant turning point for him. The source revealed that he deeply missed her and was determined to prevent their children from experiencing a fractured family. Stiller came to a realization of what he had lost only after the separation occurred.

During the COVID-19 pandemic, the director of Reality Bites took the opportunity for extensive self-reflection, which ultimately played a pivotal role in reigniting his romance with Taylor. "He actively decided to no longer fret over trivial matters and instead focused on redirecting his energy, finding common ground with Christine on those insignificant issues that ultimately held no significance in the grand scheme of things," disclosed the insider.

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March 2022

The couple appeared joyful while attending the BNP Paribas Open tennis tournament in Indian Wells, California. According to an eyewitness, the star of "Meet the Parents" and the actress from "The Wedding Singer" seemed delighted together. They walked in with him having his arm around her, and throughout the match, they shared many laughs and exhibited animated behavior.

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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

During an episode of her podcast "Hey Dude ... The 90s Called!", Taylor and her husband discussed the casual start of their relationship. They both acknowledged being each other's rebound at the time.

The star of The Secret Life of Walter Mitty, chimed in, "We didn't really take it seriously." Stiller further elaborated that he had invited his future spouse to "come and spend time" in New York City while he was shooting the romantic comedy Keeping the Faith in 2000.

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

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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

During an interview on The Drew Barrymore Show, Taylor discussed her and Stiller's reconciliation. She explained that although family had always been a priority, both she and Ben started to grow apart. Their decision to separate was made with careful consideration and they chose not to discuss it publicly. They were at a point where they needed to figure out what was best for them in that chapter of their lives, which was about three or four years ago.

During the pandemic, their continuous period at home enabled them to realign their perspectives. "With two teenagers, we all coincidentally ended up staying together in our house," Taylor elucidated. "We had ample opportunities to engage in conversations, without any competing distractions. ... It simply occurred naturally." 

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October 2023

Stiller and Taylor, along with their son Quinlin, made a rare appearance on the red carpet at the Project ALS 25th Anniversary gala celebration in New York City. They cohosted the event and Taylor shared with Entertainment Tonight that they intended to work as a cohesive "team" on stage, humorously referring to themselves as both the yin and yang.