The two met on the audition of a show titled 'Heat Vision and Jack' which never made to the television, but it was the beginning of their relationship.
When Ben Stiller saw his ex-wife Christine Taylor at the audition of a new comedy series titled Heat Vision and Jack, for which he was expected to direct a pilot episode, Stiller knew that he and Taylor have some connection.
Talking to Parade in 2016, the actor recalled, “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.” Even though the show got stalled, the sparks between the two actors flew and they found themselves staying together for 18 years.
“When I met her, I pretty much thought, ‘That’s the person,'” Stiller told ET in 2007 recalling his 1999 first meeting with Taylor. "It was like, 'Wow, this is a great person. I love her.'" That was also the time when Stiller was ready for another chance at love after a breakup from actress Jeanne Tripplehorn. “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.” He jokingly added that since they were "both on the rebound, we just jumped.”
In no time, Stiller found himself falling really hard for Taylor. “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."
After just a year of dating, The Night at the Museum star proposed to Taylor as he felt that their union was meant to be. “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 said. However, there was something that he did a little differently which is usually not heard of when it comes to marriages in Hollywood. Stiller went the old-fashioned way to ask Taylor's hand in marriage.
“I asked her father for permission before I did it,” he revealed, “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…’” Stiller recalled. "He’s a man of few words but he was very welcoming. I was more nervous asking him than asking her."
In May 2000, with Taylor's father's blessings, the couple walked down the aisle in Hawaii, and just two years later, the love birds welcomed their daughter Ella Olivia. Then in 2005, the couple became parents to son Quinlin Dempsey.
The couple pretty quickly figured out how to balance work and life. In 2011, Taylor told Huffington Post, “One of us is with the kids while the other one is working.” The actress took a backseat from work to concentrate on her family. “She made the choice to be a mother first to our kids," Stiller revealed. "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.”
However, the couple shocked everyone when in a joint statement to People in 2017, they revealed they were splitting after 17 years of marriage. They stated that “with tremendous love and respect for each other” they have decided to separate but their “priority will continue to be raising our children as devoted parents and the closest of friends.” Even after their separation Stiller and Taylor have stepped out together in public. In 2018, they accompanied daughter Ella to the US Open, and in 2019 they were seen at the Pretty Woman: The Musical on Broadway with both kids.
Following their split, the exes were seen together at the 2019 Emmy's as well giving rise to speculations whether the former flames were trying to reconcile their relationship. But it seems that they are neither ready for divorce nor stepping up for reconciliation, however, there is no way that the couple is going to let anything destroy the bond they nurtured for nearly two decades.
Whether they get back together or not, they are proof that one can maintain love, respect, and friendship with the one you once gave your heart to.