Ben Stiller and Christine Taylor's Relationship Timeline: Comedy Co-Stars, Marriage and Reconciliati

Ben Stiller and Christine Taylor's decades-spanning marriage is sure to go down in Hollywood history! 

The comedy co-stars met on set in 1999 before tying the knot less than a year later. Stiller and Taylor went on to build a family with their two children, Ella Olivia and Quinlin Dempsey. 

Stiller caught up with ET in 2007, where he explained that Taylor was "the one" from day one. "When I met her, I pretty much thought, 'That's the person.' It was like, 'Wow, this is a great person. I love her,'" he said at the time. 

The couple went on to star together in several Blockbuster comedies throughout the decades to come such as Dodgeball: A True Underdog Story, Tropic Thunder, Zoolander and Zoolander 2.

In 2017, however, the beloved co-stars announced their separation, despite the duo was spotted several times together before announcing their relationship had rekindled in February 2022. 

From on-screen romance and laugh-out-loud movie moments to a real-life partnership, scroll down to explore this complete timeline of Ben Stiller and Christine Taylor's relationship. 

1999: TV Pilot Meet-Cute

In 1999, Stiller was working on a TV pilot for the Fox series, Heat Vision and Jack, which never made it to air. Despite the series not getting greenlit, Stiller met Taylor, his wife-to-be, on that set! She was auditioning for the role of "sexy sheriff."

During an interview with Parade in 2016, Stiller reminisced about meeting Taylor during auditions for the series -- explaining that they were both coming out of relationships at the time. 

"I was directing a pilot for Fox, starring Jack Black, called Heat Vision and Jack [1999]. My wife came in to audition for the role of the sexy sheriff," Stiller told the publication. "She had been in the Brady Bunch movies and they were pushing her on me. She came in and she was great … I was single. I'd come out of a long relationship with [actress] Jeanne Tripplehorn. Christine was coming out of a relationship too. We went on a date and it clicked. We were both on the rebound. And we just jumped."

June 1999: MTV Movie Awards Debut 

Not long after meeting, Stiller and Taylor made their red carpet debut as a couple on June 5, 1999, at the MTV Movie Awards. Stiller was nominated for four awards for his role in the film, There's Something About Mary -- he took home the award for Best Fight. 

Taylor may have been his date to the award show, but Hollywood history buffs will remember Stiller smooching his canine co-star, Puffy the Dog, in the audience! 

November 1999: Meet the Parents Proposal 

As the old adage goes -- life imitates art! Before Stiller proposed to Taylor, he asked her parents for permission to do so. It just so happens the actor-director was rehearsing for his film, Meet the Parents, which was in the works. 

Stiller later recounted the fateful event to Parade in 2016, saying, "I proposed to Christine when I was rehearsing Meet the Parents ... I asked her father for permission before I did it ... It was like Meet the Parents in real life, because Christine's father is an intimidating guy who owns a security company." 

 "We're good friends now, but at the time I was in the basement rec room saying, 'I really would like to marry your daughter …' He's a man of few words but he was very welcoming. I was more nervous asking him than asking her," Stiller said. 

May 13, 2000: Hawaiian Wedding 

After a whirlwind romance of less than a year and a six-month engagement, Stiller and Taylor got married in Hawaii on May 13, 2000. The pair's nuptials took place at an oceanfront estate on the island of Kauai in front of friends and family. 

September 2001: On-Screen Love Interests

Stiller and Taylor made their first Blockbuster collaboration together in the 2001 cult comedy, Zoolander. The real-life husband and wife played the unlikely duo of journalist Matilda Jeffries (Taylor) and eccentric male model Derek Zoolander (Stiller). 

April 9, 2002: Welcomed their First Child

Stiller and Taylor welcomed the birth of their daughter, Ella Olivia, on April 9, 2002. Born into a Hollywood dynasty, Ella would go on to be featured in several films such as Megamind, Night at the Museum: Secret of the Tomb and Escape at Dannemora.

When Ella was just 2 years old, Taylor already knew the apple didn't fall far from the tree. Speaking with People in 2004, Taylor said, "It's not even funny how much (Ella) is like Ben. She's definitely a ham."

June 2004: Return to the Big Screen

After the success of their first film collaboration, Stiller and Taylor came together once again in the comedy Dodgeball: A True Underdog Story. Though this time, Taylor and Stiller were not exactly love interests -- as he played the hilarious film's villain, White Goodman. 

During an interview with IGN Stiller gushed about working with his wife and joked that acting in the sports comedy was "couples therapy." 

"It was fun. We had fun, we were laughing a lot, we got to spend time together which was good. When you're working, you don't get to do that," Stiller explained, at the time. "And she, we just connect on that level … We laugh at the same things, so it was actually really fun and therapeutic. It's always good to throw balls at each other. It would be good therapy, good couples therapy."

Taylor explained that while the duo "had a blast" on set, it was difficult for her to be away from their young daughter. "This is the first movie we did together since having our daughter, so there were endless challenges personally," Taylor explained. "When we did Zoolander, we were newly married … It was sort of almost an extended honeymoon."

July 10, 2005: Welcomed their Second Child 

Taylor gave birth to her and Stiller's second child, a baby boy, Quinlin Dempsey, on July 10, 2005. Just like his older sister, Quinlin would go on to have roles in Megamind, Night at the Museum: Secret of the Tomb and a voice role in Madagascar: Escape 2 Africa.

In 2013, Stiller reflected on Taylor's pregnancy and becoming a father of two during an interview with Parade. 

"When your wife is pregnant for nine months, you get used to the idea of pregnancy. Obviously, you know where it's leading, but it almost becomes this abstract idea; and then suddenly the next time you go back to the house, you have another person living with you. Who you've just met. Your child … I was thinking moment to moment: Just get her from the baby carrier to the crib … It's a short distance but a huge change," he said. 

August 2008: Another Blockbuster Hit Comedy 

Cementing the duo as comedy legends, Stiller and Taylor returned to the big screen in Tropic Thunder. Stiller wrote, directed and starred in the wartime thriller-comedy where Taylor played the role of Rebecca. 

The meta film follows Stiller, a war movie director, as he drops actors into the middle of a real jungle, claiming he is going to capture their performance with hidden cameras.

Taylor took a two-year hiatus from acting after her work on Tropic Thunder to dedicate time to their children. 

December 2010: Balancing Careers and Family Life 

After stepping away from the spotlight, Taylor starred in the Christmas film, Farewell Mr. Kringle. The actress explained that she was able to do so because Stiller had a break between films to "take over mom duties." 

In an interview with The Morning Call, Taylor discussed their family dynamic on and off-screen. "It happened so naturally. When I married Ben, I just decided to go with him. He travels so much. It was a no-brainer. I wanted to be with him. And sometimes I got to be in his movies and work with him, which I loved."

She continued, "Then, when I had Ella, my whole world changed. I couldn't believe how much love I had for this little creature. I wanted to be a part of it all. I didn't want to miss anything, and with Ben working as much as he does, I felt it was important for one of us to be the stability in the family."

Speaking of her role in Farewell Mr. Kringle, Taylor said, "It was really the first time that I could even think about working because Ben could take on the mom responsibilities."

October 2014: Getting Older 

Stiller and Taylor made a red carpet appearance at the 16th annual Tomorrow Is Tonight Gala for Project A.L.S. in New York. The couple caught up with People and reflected on their 14-year marriage. 

"It's all change for the better. Right? We're older, we're wiser," Taylor said. "We're hopefully getting better," the actress added as Stiller agreed. "I found a picture of us from 15 years ago and I saw youth. You don't see [the change] on a daily basis. We looked like kids. Now we look like parents."

February 2016: Reprising their Zoolander Roles 

The long-awaited sequel to Stiller and Taylor's first film collaboration, Zoolander 2, hit theaters in February 2016. The couple was joined by their children at the film's New York City premiere. 

Stiller caught up with ET on the red carpet where he discussed the key to success for his longstanding marriage. 

"Having a sense of humor," the actor-director said. "I think you got to laugh. Because you know, after a while, life is life," he shared. "We all have to deal with what life throws at us, so you got to have a sense of humor about it. If you can share that, at the end, it makes a huge difference."

May 26, 2017: The Shocking Separation 

Breaking the hearts of comedy lovers everywhere, Stiller and Taylor announced their separation in a joint statement on May 26, 2017.

In an exclusive statement to ET, Stiller and Taylor said, "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 couple announced. "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." 

September 2019: Reunited at the Emmys 

Despite their separation announcement, Stiller and Taylor were spotted at several public outings together in years to come. In 2019, Taylor attended the Emmy Awards where Stiller was nominated for Outstanding Directing for a Limited Series, Movie or Dramatic Special for his work on Escape At Dannemora.

The duo, though still separated, arrived together and posed with each other for photos on the red carpet. 

October 2020: Back to Business 

Stiller and Taylor both worked on the 2020 holiday comedy, Friendsgiving. Taylor starred as Brianne and Stiller served as a producer on the project. 

February 2022: Stiller and Taylor are Officially Reconciled!

In an interview with Esquire in February 2022, Stiller announced that he and Taylor were officially back together -- and credited the COVID-19 pandemic for saving their marriage. 

Stiller explained that when the pandemic hit, he moved back home with Taylor to be with their children. "Over the course of time, it evolved," he told the magazine. "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."

Stiller explained that since reconciling their marriage, he and Taylor were more on the same page. "I think we have a respect for the ways that we’re similar and the ways we’re different," he said. 

April 2022: Happier Together 

Stiller caught up with ET in April 2022, where he chatted about his renewed marriage with Taylor. 

“I’m so happy where I’m at in my life and the fact that we're even able to be here together doing this right now, all those things are now not taken for granted,” the Severance director said. “The whole last few years have been a time for everybody to kind of get in touch with a lot of that.”

August 2022: U.S. Open Date Day 

Stiller and Taylor were spotted attending the U.S. Open at the USTA Billie Jean King National Tennis Center in Queens, New York in August of this year. 

The pair was seen smiling, laughing and enjoying each other's company as they watched Rafael Nadal of Spain complete a first-round victory over Australia's Rinky Hijikata.

November 2022: Broadway Date Night 

Fans can't get enough of seeing Stiller and Taylor out and about together! In November of this year, the couple was seen in NYC attending Mike Birbiglia's opening night of The Old Man & the Pool on Broadway. 

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