Ben Stiller and Christine Taylor Prove That Divorce Doesn’t Have To Mean the End of Love

Inspiring Stories

It was work that brought Ben Stiller and Christine Taylor together — and laughter that kept them happily married for 17 years. The pair first met in 1999 when Stiller was in charge of directing a pilot for a new comedy series called Heat Vision and Jack, which was set to star Jack Black and air on Fox. As the actor recalled during an interview with Parade, “My wife came in to audition for the role of the sexy sheriff. She had been in the Brady Bunch movies and they were pushing her on me. She came in and she was great.” 

The show didn’t take off, but their attraction did. Stiller was smitten and following that initial encounter, he and Taylor soon realized that they shared a unique connection. A whirlwind romance followed, leading to marriage, kids, and an unshakable bond that cannot be tainted — not even by a split. 

Inside Ben Stiller and Christine Taylor’s sweet 18-year union 

Ben Stiller and Christine Taylor (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)

Not everyone believes in an instant connection or love at first sight, but that’s exactly what Ben Stiller experienced. “When I met her, I pretty much thought, ‘That’s the person,’” Stiller told ET, recalling his 1999 encounter with his future wife.

It was like, ‘Wow, this is a great person. I love her.’

Ben Stiller

The timing may not have been absolutely perfect, but Stiller was single and ready to take a chance. “I’d come out of a long relationship with [actress] Jeanne Tripplehorn. Christine was coming out of a relationship too,” he revealed. “We went on a date and it clicked.” Joking that they “were both on the rebound,” he added, “We just jumped.”

The courtship that followed was the definition of a whirlwind. So much so that Stiller didn’t even realize he was falling, hard. “Our relationship was a gradual thing that happened over a quick period of time, maybe seven or eight months,” he told Parade.

We just started hanging out with each other and it developed into, ‘Wow, this feels great. I really like this person. I think I love this person. I really do — I love this person.’ It hit me out of the blue.

Ben Stiller

As the Zoolander star went on to admit, he and Taylor “got married pretty quickly” (they hadn’t even been dating a year when he proposed), but he felt that their union was right and he never once questioned it. “I turned around one day and said, ‘Wow, I’m happy with her. We connect. I’m enjoying being with her all the time!’ It just felt right,” he shared.

But while they chose to ignore convention and jump into marriage rather fast, there was one thing Stiller decided to do the old-fashioned way. “I asked her father for permission before I did it,” he said, joking, “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 continued.

He’s a man of few words but he was very welcoming. I was more nervous asking him than asking her.

Ben Stiller

With that blessing bestowed, the couple wasted no time saying “I do” and tied the knot in Hawaii in May 2000. In April 2002, they welcomed daughter Ella Olivia — “It’s not even funny how much she is like Ben. She’s definitely a ham,” Taylor once told People — and in July 2005, they had son Quinlin Dempsey. 

They struck the right work-life balance 

Ben Stiller and Christine Taylor in Zoolander (credit: Zoolander movie)

Over the years, Ben Stiller and Christine Taylor managed to effortlessly blend personal with professional time and time again. They starred in countless movies together, like Zoolander, Dodgeball: A True Underdog Story, and Tropic Thunder, and as Taylor gushed to ET, acting opposite Stiller “is the best. I mean, I think that, you know, the reality is there’s such an unspoken connection,” she explained.

When it came time to start their family, however, they had to recalibrate that balance and they did so willingly. As Taylor told Huffington Post in 2011, “One of us is with the kids while the other one is working.” That meant that she eventually had to cut back on acting more than her husband. As Stiller told Parade in 2016, “She made the choice to be a mother first to our kids. A few years in, she said, ‘I think this is what I need to do.’ She felt she needed to be there. I feel very fortunate for our kids.” But she didn’t allow that tough decision to sow animosity between them. Because when you’re a true team, you want what’s best for both sides.

Another major secret to the couple’s long marriage? Laughter. “I have to say, sense of humor is the greatest thing,” Taylor told ET and Stiller agreed. “I say that’s the secret to a happy marriage anywhere in any city, not just Hollywood,” he reasoned.

I think you got to laugh, because after a while, you know, life is life. We all have to deal with what life throws at us, so you got to have a sense of humour about it. If you can share that, at the end, it makes a huge difference.

The Night at the Museum star also shared a similar sentiment with Parade, telling the mag that his marriage with Taylor worked so well “because we both want to make it work. We both love each other, and we also laugh a lot. She’s one of the funniest people I know.” 

A separation doesn’t have to mark a finite end

Ben Stiller and Christine Taylor’s perfect balance seemed to go off-kilter in May 2017 when the pair announced that they were splitting after 18 years together (17 of those married). In a joint statement to People, they said that the decision to separate was made “with tremendous love and respect for each other” and underscored the fact that their “priority will continue to be raising our children as devoted parents and the closest of friends.” 

And they weren’t kidding. While one insider told People that the actor’s hectic work schedule was to blame for the divorce — “He has a very busy Hollywood career, and she’s been very focused on being a mom” — the exes made it immediately clear that they were serious about putting family above all else.  

Since the announcement first made headlines, Ben Stiller and Christine Taylor have repeatedly stepped out together, showcasing their unbreakable connection. 

In August 2018, for example, they took daughter Ella to the US Open and according to People they were all “sporting bright smiles.” In April 2019, they went to see Pretty Woman: The Musical on Broadway with both kids and posed for photos backstage. “It was a sweet family night out. The kids were glowing because they all love the theater, and Ben and Christine looked happy together, smiling and laughing and holding hands, especially during intermission,” an insider told People, adding, “They seemed to really love the show and being around one another.” The following month, they were snapped backstage at another show, What the Constitution Means to Me

Honoree Ben Stiller and Christine Taylor pose at the 2019 Rosie’s Theater Kids Fall Gala at The New York Marriott Marquis on November 18, 2019 in New York City. (Photo by Bruce Glikas/WireImage)

Their joint outings haven’t slowed down any, as Taylor has continued to support Stiller’s achievements. Two years after announcing their split, the exes attended the 2019 Emmys together. Stiller was nominated for directing Escape at Dannemora and the pair walked the red carpet, posed for photos and, once inside, an onlooker told Us Weekly that they never left “each others’ sides.”

The source also noted how Taylor “was smiling and leaning forward and in toward” Stiller. That November, they were spotted at Rosie O’Donnell’s RTKids Gala where Stiller was being honoured and, what’s more, they haven’t stopped acting together. Both Stiller and Taylor appeared in 2020’s Friendsgiving.  

Are Ben Stiller and Christine Taylor giving love another chance? 

NEW YORK, NEW YORK – OCTOBER 23: Ben Stiller, Ella Olivia Stiller and Christine Taylor attend Project ALS 21st Annual New York City Gala at Cipriani 42nd Street on October 23, 2019 in New York City. (Photo by Dimitrios Kambouris/Getty Images)

Not only do Ben Stiller and Christine Taylor share a family, but their nearly two decades of joint experiences have resulted in an unshakeable foundation and a unique friendship. They’ve been through a lot together, both good and bad, like when Stiller secretly battled prostate cancer at the age of 48.

Speaking with Howard Stern in 2016, the actor surprised fans by revealing that he had quietly beaten the cancer. “I was scared,” he admitted, noting, “The one thing that it does is it just stops everything in your life.” Taylor was undoubtedly a major source of strength and courage in his darkest hour and this type of bond doesn’t just disappear overnight. 

Which explains how Stiller and Taylor have managed to remain so close, sparking chatter of a reconciliation. As of August 2018, the exes still hadn’t filed court papers to finalize their divorce and Star magazine reported (via Closer Weekly) that they may have called it off. Noting a two hour-long dinner date, one source told the outlet, “Judging by how cozy they looked, you would never guess that they were exes. Ben and Christine insist that they’re staying friendly for the sake of their kids, but it hasn’t gone unnoticed that they’re still acting like a couple.” 

Another insider described Stiller as being “lonely and miserable” following the split and added that it drove the actor to have a major realization. “They had their problems, but Ben knows he’s never going to meet someone like her again. He’s started to wonder if he didn’t put enough work into the relationship, and he’s been kicking himself that he let her go,” the source claimed. 

Meanwhile, a reported friend told the mag, “It’s telling that neither of them is moving forward with the divorce right now. There’s still a lot of love between them, and it’s clear the spark never went away. They’re just taking each day as it comes.”

Jump to April 2019 and a source told Closer Weekly that Ben Stiller and Christine Taylor were indeed “giving their marriage another shot. He never got over her after the split nor was he interested in starting a relationship with anyone else whilst they were separated,” they said.

Whether or not a romantic reconciliation is in their future, Ben Stiller and Christine Taylor can teach us all an invaluable lesson: Their unwavering unity following their split truly proves that a breakup doesn’t need to symbolize the end of love, respect, nor friendship.

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