A Timeline Of Ben Stiller And Christine Taylor's Relationship

If there's one thing we love here at Nicki Swift, it's a Hollywood love story. Okay, we'll admit it, we do love a little drama too. Nonetheless, it's always nice to see those couples who make it work year after year. There are some famous duos who like to keep us on our toes, though. Couples who make us wonder where they stand with each other and what's really going on behind closed doors. One of those couples is Ben Stiller and Christine Taylor. 

These two have been dating, married, separated, and pretty much everything in between, since they first got together in the late 1990s. As such, they've proved to us that there's no timeline on love, and that there's always hope for a healthy co-parenting situation (and maybe more ...).

When asked in 2016 why he and Taylor work so well together, Stiller told Parade, "Because we both want to make it work." He added, "We both love each other, and we also laugh a lot. She's one of the funniest people I know." That same year, he doubled down on that theory to ET, by admitting that the "secret" to their happy marriage was "having a sense of humor." 

Sadly, it was hard to have a sense of humor about their breakup, and within a year of that statement being made, they went their separate ways ... at least for a little while. This is the timeline of how these two lovebirds have navigated that fragmented relationship.

Ben Stiller first met Christine Taylor in 1999 during auditions for the TV show "Heat Vision and Jack," and the rest, as they say, is history. Just kidding! There's obviously a whole lot more to their romance timeline than that, and we're going to kick it off by letting Stiller describe their significant meet-cute. "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," he told Parade in 2016. He explained that they'd both just come out of long-term relationships and were "on the rebound," but went on a date and "clicked" right away.

As to who they may have been rebounding from? Stiller dated Jeanne Tripplehorn from 1990 until 1996, and the two had what news.com.au described as "a roller coaster romance," with the couple getting engaged in 1993. Taylor has a famous ex, too. She dated Neil Patrick Harris between 1997 and 1998 — but we're guessing we don't have to tell you why that one never worked out.

"Heat Vision and Jack" never made it to air, but it was enough to create a spark onscreen and off. While speaking to ET in 2017, Taylor suggested why she and Stiller work so well together, and said, "The reality is there's such an unspoken connection. I feel like for us, when we first met, it was on set ... He's amazing."

First comes love, then comes marriage! In November 1999, Ben Stiller popped the question and just six months later, he and Christine Taylor jumped the broom during a romantic ceremony on a Hawaiian beach. Stiller opened up about how quickly things progressed in 2016 when he admitted to Parade that they both "just jumped" and "got married pretty quickly."

In another interview with Parade, the "Tropic Thunder" star described the romance as "a gradual thing" which evolved over "maybe seven or eight months." He explained, "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.'" Stiller further recalled that his love for Taylor "hit [him] out of the blue." Aww ...

Apparently his proposal was something straight out of a movie — a comedy, to be precise, as the actor likened the beginning of their matrimonial situation to being "like 'Meet the Parents' in real life." Speaking to the outlet, he recalled asking Taylor's somewhat tough father for permission for his daughter's hand in marriage, and admitted that he was actually "more nervous" speaking to Taylor's dad than he was speaking to his wife-to-be about spending their lives together. Hopefully, for Stiller, a polygraph machine wasn't part of that process ...

After tying the knot, Ben Stiller and Christine Taylor's on-screen relationship continued alongside their off-screen one, with the couple starring in a slew of big movies together. One of the biggest was 2001's "Zoolander," in which Stiller starred as a male model who learns there may just be more to life than being really, really, ridiculously good-looking. Taylor played his love interest Matilda Jeffries, and (spoiler alert!) the two characters end up together and welcome a Blue Steel-posing baby at the end of the movie.

That's not all, though. Another huge project they took on together was 2004's "Dodgeball: A True Underdog Story," where Stiller played self-obsessed gym owner White Goodman and Taylor appeared as antagonistic accountant Kate Veatch. In a twist of fate (spoiler alert, again) they didn't end up together this time, with Taylor's character instead getting together with Vince Vaughn's Peter LaFleur.

Of the change in their on-screen dynamic between the two movies  — being attracted to and then disgusted by, Stiller's respective characters —Taylor told IGN, "To me, he's my husband. He can't look bad in anything. That being said, I loved being the nemesis. I loved it. I loved being repulsed." They also hit the set for a slew of other big movies over the years, starring alongside one another in the likes of "Tropic Thunder," and working together on "Friendsgiving," for which Stiller was a producer. Clearly, the couple who works together stays together. At least, for a while.

Now it's time for that baby carriage! Ben Stiller and Christine Taylor officially became parents for the first time in 2002 when they welcomed a daughter named Ella Stiller. Ben opened up about his paternal experience to Parade in 2013, admitting, "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."

Though the two have tended to keep their kids a little more out of the spotlight, Taylor told People in 2004 that Ella was like a mini version of her famous father, admitting, "It's not even funny how much [Ella] is like Ben. She's definitely a ham." Ben clearly got used to the idea of sharing his home with the kiddos though, as the couple welcomed their son, Quinlin, into the world in July 2005.

Shortly after that, the "Search Party" star took a step back from her career to be at home with their children, which explains why you may not have seen her for a while. "She made the choice to be a mother first to our kids," Ben told Parade in 2016. "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."

Prepare yourself, Bhristine fans (yes, that's the couple name we're trying out for Christine Taylor and Ben Stiller) as here's where things start to get a bit rocky. After welcoming their two kids to the world, the pair seemed to still be happily in love. Sadly, however, that may not have been the case as Taylor and Stiller split in 2017, making their separation official via a public announcement.

The parents of two confirmed the heartbreaking news via a joint statement issued to Entertainment Tonight, which read, "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. Our priority will continue to be raising our children as devoted parents and the closest of friends."

They also asked for privacy as they navigated the breakup, but that didn't stop the rumor mill from churning up potential reasons for the two going their separate ways. A source claimed to People, for instance, that their schedules and responsibilities had supposedly contributed to the surprising breakup, alleging, "It gets hard — he has a very busy Hollywood career, and she's been very focused on being a mom."

Just one month after they announced their split, Ben Stiller and Christine Taylor were back together ... sort of. June 2017 saw the release of a hilarious Omaze clip starring the newly separated twosome, in which they reprised their "Dodgeball: A True Underdog Story" characters. The two were joined by co-stars like Vince Vaughn and Justin Long in the short reunion video, which was put together as a fundraiser for The Stiller Foundation — an organization founded by the actor to support children through education across the globe.

It's not clear if the video was filmed before or after the duo officially went their separate ways, though seeing the former couple being cordial onscreen probably wasn't too surprising for fans of the two comedy talents. Shortly after they announced their split in May 2017, a source alleged to People that Stiller and Taylor were still "a very loving family" who "respect each other and will do anything to make sure their kids are happy." The outlet suggested that a "messy uncoupling" wasn't to be expected from the couple based on the source's claims. By all accounts, there would be further evidence to support these claims ...

If teaming up for that reunion video didn't prove Ben Stiller and Christine Taylor were still on good terms after their breakup, they made it very clear away from the spotlight too. In July 2018, a year after announcing their separation, they were spotted eating together at a restaurant in New York City, seemingly without their kids. People shared candid paparazzi snaps of the two looking pretty happy together in the Big Apple, with a source telling the outlet that they "remain friendly and devoted parents to their kids."

An onlooker who claimed to have seen Taylor and Stiller out on their NYC dinner date alleged to Star Magazine (via Closer Weekly) that they appeared to be "still acting like a couple." They added, "Judging by how cozy they looked, you would never guess that they were exes." But that certainly wasn't the only time they put up a united front. The former couple were spotted together several other times in the wake of their split, including when Stiller and Taylor attended the 2018 U.S. Open alongside their daughter, Ella.

It was around the same time that the two also proved they could keep working together as friendly exes with no drama, when the movie "Friendsgiving" dropped in October 2020. Taylor starred in the comedy alongside the likes of Malin Åkerman, Kat Dennings, and Aisha Tyler, while her estranged husband served as co-producer under his Red Hour production company.

All those cozy sightings of Ben Stiller and Christine Taylor were a feast for gossip lovers, with reports claiming that the split was off, and they were instead giving their marriage another go. In August 2018, Star Magazine alleged (via Closer Weekly) that the couple's "$200 million divorce" had been "called off," with a source claiming there was "still a lot of love between them, and it's clear the spark never went away." The couple, according to the source, were "just taking each day as it comes."

It was later alleged that neither had actually dated other people during their separation period, with People claiming that both stayed true to one another even after announcing their breakup. "They were never estranged," an insider claimed. "Ben just had such a busy career for years. It drove them apart a bit. They didn't spend much time together. But when they did, it was always obvious that they loved each other." The anonymous source added that the pair still "always had fun and enjoyed hanging out." And honestly, who wasn't rooting for them to make it work?

Though Ben Stiller and Christine Taylor never officially confirmed that their relationship was back on, they certainly set tongues wagging in April 2019 when they were spotted looking affectionate while attending "Pretty Woman: The Musical on Broadway" with their children. "Ben and Christine looked happy together, smiling and laughing and holding hands, especially during intermission," an onlooker claimed to People, suggesting that the two "seemed to really love the show and being around one another."

That same month, a Closer Weekly source claimed the are-they-aren't-they couple were officially "giving their marriage another shot," and shared that Stiller supposedly "never got over [Taylor] after the split nor was he interested in starting a relationship with anyone else whilst they were separated." As rumors concerning their reconciliation continued, the "Zoolander" co-stars remained hush-hush about what was really going on between them. However, they appeared to make a pretty strong public statement together in September 2019. 

In a move rarely seen from Hollywood exes, Stiller and Taylor attended the Emmys together, happily posing for photos with their arms around one another while on the red carpet. It had been two years since they'd officially announced their separation, and yet the couple were showing very few signs of having actually separated ...

Here we go, folks, the news we've been waiting for: In February 2022, Ben Stiller and Christine Taylor officially reunited, although there had arguably been evidence to support their rumored reconciliation for a while. The "While We're Young" star dropped the exciting news while speaking to Esquire, sharing that he and Taylor had moved in together at the beginning of the Coronavirus pandemic, in order to be there for their two children. Things "evolved" from there. 

"We were separated and got back together and we're happy about that. It's been really wonderful for all of us," he told the outlet, calling his reunion with Taylor "unexpected." Following Stiller's revelation about his marriage, a source later suggested to People that the couple's friends all "hoped they would get back together." They further alleged that the bonds of their family may have pulled them back together. "When the pandemic hit, they decided to live together with their kids. They were always very close with their kids. Both are amazing parents."

Giving us hope in love and producing a (very rare) good thing as a result of the pandemic? Yep, it's official, we love Taylor and Stiller more than ever. Whatever happens, there's no doubting this is one couple who will continue to do the best for their children and show us what it really means to not give up on love.