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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 her future husband.

“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.

In 2021, the couple’s two-decade-plus relationship is still going strong. They share two daughters, Maude and Iris, and have created a number of beloved movies as a family of funny individuals.

Scroll down to take a look at Apatow and Mann’s relationship through the years:


June 1997

The pair wed on June 9, 1997, in Los Angeles. 

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December 1997

Meet Maude! The couple’s first daughter was born on December 15, 1997.

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October 2002

The happy family added another daughter, Iris, on October 12, 2002.

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June 2007

Knocked Up, which was directed by Apatow, premiered on June 1, 2007. The film starred the couple's daughters and Mann, who played her children's mother in the movie.

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December 2012

This is 40, a sequel to Knocked Up, was released on December 21, 2012. Leslie, Maude and Iris reprised their roles in the film, which was written, directed and produced by their family’s patriarch.

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June 2017

The pair celebrated their 20th anniversary on June 9, 2017, with Judd sharing a sweet photo from their wedding via Instagram.

“Today is the 20th anniversary of my marriage to the brilliant, hilarious, amazing Leslie Mann,” he wrote. “The greatest thing that has ever happened to me.”

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June 2018

In a conversation with Us Weekly, Mann revealed that the family is very open with each other, noting she and her daughters often go to each other for beauty advice.

“I ask their opinions and they ask mine,” the California native said. “Iris doesn’t really care what I have to say, Maude does a little more than Iris, and then I care what both of them have to say. That’s how it works!”

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August 2019

The younger Apatow daughter clapped back at her mom after she critiqued her makeup in an Instagram comment.

“Under eye concealer too light,” the Blockers actress wrote on an image of her daughters. “[Kisses], mom.”

“A text would have been nice,” the teen replied.

 

Courtesy Iris Apatow/Instagram; Shutterstock
November 2019

After the pair made headlines for fighting outside L.A. restaurant Katsuya in October 2019, the 40-Year-Old Virgin screenwriter opened up about the importance of letting feelings out on The View.

“We engage [in fights] and I think that’s why our relationship is healthy,” he said. “Then you get a call, like, ‘What do you say? We saw you guys [fighting].' I was, like, 'Really? Have you been married? Do you know what marriage is?'”

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January 2020

At the DGA Awards in Los Angeles, the director revealed how he and the George of the Jungle actress keep their marriage interesting after 22 years.

“You have to get very inventive because you’ve gone through all the good gifts and activity concepts,” the Forgetting Sarah Marshall producer told Us Weekly exclusively. “At some point, you’re like white water rafting or getting mariachi bands because nothing’s off-limits.”

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March 2021

Judd shared an Instagram photo to celebrate his wife’s birthday, proclaiming he loves her the very most.

“Happy Birthday Leslie!!! I love you. I would write more, but I feel like it would water down the impact of the “I love you.” If there is a lot of wordage around it, it could get lost and people would forget I even said it, but if that is all I say it has way more impact. Because what more is there to say, but that?” the filmmaker wrote. “I could go on and on with specific praise about this or that, but I have done that on previous birthdays and I feel like everyone does that and then I sound like I am copying John Legend or J Lo. So, let’s keep it tight. I love you. That’s it. Just that. It’s enough. No one has ever meant it more. Not Legend. Not J Lo. Not Kelsey Grammar. None of them. I love you.”

Courtesy Judd Apatow/Instagram


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