Ben Stiller and Christine Taylor Were Each Other’s ‘Rebound’

From rebounds to real love! Although Ben Stiller and Christine Taylor have been married for more than two decades, the duo revealed that their relationship started out casually.

“We were both each other’s, I would say, like, sort of rebound relationship a little bit,” Taylor, 51, shared during the Monday, January 30, episode of her podcast “Hey Dude … The 90s Called!” on which Stiller, 57, made a guest appearance.

The Zoolander actor echoed his wife’s sentiments. “We weren’t taking it seriously,” he explained, adding that the twosome met while making the 1999 TV pilot Heat Vision and Jack, which Taylor guest starred in and Stiller directed.

“We had a fun time making the show and then Christine and I connected and then I went off to do a movie [Keeping the Faith] in New York and I invited her to come hang out,” the Along Came Polly star recalled.

Taylor chimed in: “I ended up going and staying the entire summer.”

Prior to his relationship with the Brady Bunch Movie actress, Stiller dated several actresses including Jeanne Tripplehorn, Calista Flockhart and Amanda Peet. Taylor, for her part, dated Neil Patrick Harris from 1987 to 1988. The How I Met Your Mother alum, 49, publicly came out as gay in November 2006. Two years later, Harris said that his relationship with Taylor helped him come to terms with his sexuality.

“She’s the coolest, nicest chick ever. She’s an absolute catch, and I thought, ‘If I’m not going to feel the super sparks with her … it probably means I’m gay,’” the Gone Girl actor said during an April 2008 appearance on “The Howard Stern Show.”

Despite starting out as each other’s respective rebounds, Stiller and Taylor tied the knot in 2000, one year after they met. During Monday’s podcast appearance, the Tropic Thunder actor admitted that the duo’s engagement bore similarities to a film he was making at the time.

“We got engaged around when I was shooting Meet the Parents … Christine’s dad had a security company — and still does — and so it was kind of this weird parallel. He was very much like the Robert De Niro character to me,” the New York native quipped to Taylor’s cohost and Hey Dude costar, David Lascher.

However, the Craft actress contested her husband’s version of events. “Dad, I know you’re listening. You were not intimidating,” she joked.

Taylor and Lascher, 50, have a romantic history of their own. The pair dated as teenagers while filming the Nickelodeon comedy Hey Dude, which aired from 1989 to 1991.

“Everyone has that one teenage or young adult relationship that crushes them,” Lascher exclusively told Us Weekly of the romance earlier this month while promoting the podcast launch with Taylor. “We had a nice run. We had so many good times. Honestly, I remember the good times, the laughs, the love. And then I remember one summer being crushed. But it happens, you know?”

The Wedding Singer actress, meanwhile, added: “David, like you said, I broke your heart and I felt terrible. And then you would get mad at me and then I would probably say, ‘Let’s try to do this again.’ And then it wouldn’t work.”

More than 30 years after Hey Dude went off the air, the Nickelodeon alums can laugh about their relationship. On Monday, Stiller asked Lascher how he’d gotten along with Taylor’s mother during their relationship.

“Is there a sweeter person on the planet?” the Blossom alum replied. The Night at the Museum star shot back: “If she approves of you.”

Stiller and the Search Party actress share daughter Ella, 20, and son Quinlin, 17. The pair announced that they were separating in May 2017 but later reconnected, officially confirming their reconciliation in February 2022.

“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 told Esquire at the time.

One month later, a source exclusively told Us that the temporary split had been “a serious eye-opener” for the Royal Tenenbaums actor. “He missed [Christine] terribly and hated the idea of their kids growing up in a broken home,” the insider said.