Leslie Mann and Judd Apatow’s Relationship Timeline

Funny Valentines, indeed! When Judd Apatow signed on to produce the 1996 film The Cable Guy, he had no idea he’d be meeting the love of his life, Leslie Mann, during pre-production.

Or maybe, deep down, he did know something big was about to happen.

“‘There goes the future Mrs. Apatow,’” the University of Southern California alum recalled himself saying, according to an interview the pair did with Elle Magazine in 2012. “I had a soul connection instantly. I meant it. That’s why I remember it.”

Though Mann had a crush on the film’s director, Ben Stiller, she decided to move past casting call jitters and see how things would go with Apatow.

“I was in a panic. Auditioning is so nerve-wracking,” the actress recalled.

Still, she agreed to join Apatow for a dinner date at his house before a basketball game, where the producer served “spaghetti with Ragu sauce and Wonder Bread with Fleischmann’s margarine” before showing the Freaks and Geeks alum his favorite parts of his 1995 movie Heavyweights.

“He was trying to impress me,” Mann noted.

While she decided she was in love the morning after the date, Apatow maintains he knew the feeling at first sight.

The comedic duo wed shortly thereafter on June 9, 1997, in Los Angeles and went on to welcome daughters Maude and Iris in December 1997 and October 2002, respectively. The girls have appeared in a handful of their parents’ movies, including Knocked Up, Funny People and This Is 40, which proved to create an interesting — and hilarious — working dynamic.

“What I think was so great about Maude is she really could get in the head of what a teenage meltdown looks like, do it on film, kick ass — and then go home and have a real one, two hours later,” Apatow told Rolling Stone of his eldest child in June 2020, reflecting on her turn in This Is 40.

When asked whether he had concerns about his kids entering show business, the King of Staten Island director joked, “There have been times when I thought, ‘Maybe if I talked about other professions all the time, my kids would have more interest in those professions.’ Like, if I always talked about international law, they’d want to be lawyers.”

Overall, however, Apatow and Mann are more than supportive of their daughters’ aspirations — but encouraged them to finish high school before getting too deep in the Hollywood world.

“I’m really glad that I ended up staying in high school,” Maude told the outlet. “I feel like when they let me start acting on my own, I was actually ready.”