“I slept over, but nothing happened. We just kissed a lot. But I remember driving home feeling so happy and like … I felt like I was already in love,” Mannrecalled in an interview.
A year after their first film together hit theaters, Apatow and Mann tied the knot in an intimate ceremony in Hawaii. Six months later, the couple welcomed their first child, Maude, and in 2002, they expanded their family once more with the birth of their second daughter, Iris.
Over the course of their marriage, the comedy power couple have collaborated on numerous films together, but as of late, they’re sharing the spotlight with their two daughters — and it’s clear that they couldn’t be more proud.
Keep scrolling to see a complete breakdown of Leslie Mann and Judd Apatow’s relationship timeline.
1995: Leslie Mann meets Judd Apatow while auditioning forThe Cable Guy
Jon Kopaloff/FilmMagic
It was love at first sight for Apatow, who met Mann when she auditioned for his film,The Cable Guy. Apatow once explained that he knew he was going to marry Mann from the moment he met her.
“There goes the future Mrs. Apatow. I had a soul connection instantly. I meant it. That’s why I remember it,” Apatow toldELLE.
Meanwhile, Mann says the “nerve-racking” audition had her “in a panic” and she only remembers thinking that directorBen Stillerwas cute.
1996: Leslie Mann and Judd Apatow have their first date at a basketball game
Sometime after Mann was cast in the film, she agreed to let Apatow take her out on a date — after a little assistance from his sister. Mann remembered his sister, who was working for Stiller, often talking about how popular Apatow was with the ladies. When Mann decided to give Apatow a chance, he cooked her a dinner of “spaghetti with Ragú sauce and Wonder bread with Fleischmann’s margarine” before taking her to a basketball game.
“On the way to the basketball game, I was like … Oh! It hit me. My previous boyfriend was really mean. And I thought, [Apatow’s] nice. This is the type of person I should be with. And then we made out after the game,“Mann shared.
She admitted she ended up spending the night at his place — although they just “kissed a lot” — and on the drive home she said she “felt like I was already in love.”
June 9, 1997: Leslie Mann and Judd Apatow tie the knot in Hawaii
Mann and Apatow said “I do” in June 1997 in a very intimate ceremony in Hawaii. In fact, the only people in attendance were a banjo player and a minister. Mann, who was several months pregnant at the time,later said the experience was"fun and low pressure.” Much to her surprise, Mann noted that Apatow showed up to the ceremony clean-shaven, even though she had only ever known him with a beard.
“He was a cute mountain-man-looking Judd and on our wedding day he decided to shave his beard and showed up to our wedding clean-shaven and it really scared me because I didn’t know what he looked like without it!” Mann admitted.
December 15, 1997: Leslie Mann and Judd Apatow welcome their first daughter, Maude
Six months after tying the knot, the newlyweds welcomed their daughter, Maude, on Dec. 15, 1997.
October 12, 2002: Leslie Mann and Judd Apatow welcome their second daughter, Iris
Francois Durand/Getty
Mann and Apatow kept a low profile after starting their family and in 2002, they welcomed their second child — a little girl they named Iris.
2007: Leslie Mann stars in Judd Apatow’s filmKnocked Up
In 2007, the couple got the chance to work together again when Apatow directed Mann in his hit comedyKnocked Up. And not only did Mann get a major role, but the couple’s daughters, Maude and Iris, also joined the cast playing Mann’s on-screen children. Although the actress was hesitant about including them in the film, Apatow finally convinced her.
2008: Judd Apatow casts Leslie Mann inDrillbit Taylor
December 2012: Leslie Mann reprises her role inKnocked UpsequelThis Is 40
Andreas Rentz/Getty
March 2013: Judd Apatow opens up about his 17-year marriage with Leslie Mann
Steve Granitz/WireImage
“What makes [our marriage] work is we’re always trying to do better and understand each other. We’re both complicated people, but we want it to work and we love each other,” Apatow told PEOPLE.
June 9, 2017: Judd Apatow and Leslie Mann celebrate their 20th anniversary
In 2017, the paircelebrated 20 years of marriageand commemorated the occasion with some touching social media posts. Apatow posted a black-and-white photo from the couple’s beach wedding and gushed about his wife in the caption.
“Today is the 20th anniversary of my marriage to the brilliant, hilarious, amazing Leslie Mann. The greatest thing that has ever happened to me,” Apatow wrote.
November 2019: Judd Apatow talks about his relationship with Leslie Mann
During an appearance onThe View, Apatow discussed how he and Mann keep their relationship healthy.
“I’ve been married for 22 years. I have fought in every restaurant in Los Angeles: McDonald’s, In-N-Out Burger, Nobu — you name it,” he said. “We engage [in fights] and I think that’s why our relationship is healthy. 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?’ "
November 19, 2019: Judd Apatow and Leslie Mann make their TikTok debut
Mann and Apatowmade their TikTok debuton their daughter Iris' account in November 2019. In the video, Iris introduced her family while lip-syncing along to a song fromTeen Beach Movie. While Mann, Iris and Maude got into the video, Apatow jokingly stared blankly at the camera when it came to be his turn.
March 26, 2020: Judd Apatow writes a sweet birthday message for Leslie Mann
Gregg DeGuire/FilmMagic
For Mann’s 48th birthday, Apatow posted a touching tribute to his wife while also managing to poke fun at her Netflix viewing habits.
“Happy Birthday Leslie Mann! I love you forever! I am mad that you finishedThe Crownseason three without me, andBarryseason two andThe Liaron @Netflix but I will still love you forever. You’re the greatest! I am so lucky to get to share my life with you. But please don’t finishThe Sinnerseason three and the currentNarcosseason without me. ❤️❤️,” Apatowwrote alongside a photoof Mann posing in front of a desert background.
June 2020: Judd Apatow shares what it was like to quarantine with his family
Several months into the pandemic, Apatow opened up about what it was like to be quarantined with Mann, Maude and Iris. In a joint interview withRolling Stone, Maude admitted that during the first three weeks of lockdown her dad was “losing it” but he eventually got better and settled in.
“I decided to take a two-hour walk every morning around the house. I just circle the neighborhood, and that seems to level me out. It took me a while to figure out what to do to get positive chemicals in my body,” Apatow added.
March 2022: Leslie Mann says she still feels like she’s getting to know Judd Apatow
After over two decades of marriage, Mann said there are still things she feels like she doesn’t know about her husband — and she doesn’t mind it at all.
“I feel so lucky that I get to spend my life with him. He really is a good person. And at the same time, I feel like I do not know him at all. Who is this person walking around my house, eating my food and sneaking off into his little secret room doing secret things?” Mannjoked onLive With Kelly and Ryan.
April 2022: Leslie Mann stars in Judd Apatow’s filmThe Bubblealongside their daughter Iris
From L: Judd Apatow, Iris Apatow and Leslie Mann.Tommaso Boddi/Getty
June 13, 2022: Leslie Mann and Judd Apatow celebrate 25 years of marriage with their daughters
Maude Apatow Instagram
The parents of two reached another milestone together as a couple — their 25th anniversary. Their daughters, Maude and Iris, joined them for a boat party and the whole family wore old Hollywood, 1920s-inspired ensembles.
The couple’s older daughter, Maude, posted aseries of photoson her Instagram to honor her parents' lasting love, including a cheeky boat selfie with Mann and Apatow in their flapper attire and a photo of Mann with the ocean coastline view in the back.
“Happy 25th anniversary to my parents ❤️ I love you,” Maude captioned the post.
“Weeee!!!!! I love you!❤️❤️❤️,” Mann commented.
October 18, 2022: Leslie Mann and Judd Apatow attend Academy Museum Gala
Before heading into the gala to watch the iconicDiana Rossperform, Mann and Apatow posed for a few pictures on the red carpet.
Mann wowed in a cutout black gown, while Apatow looked handsome in a black tuxedo.
“Date night at the Academy Museum Gala! I love you@dianaross❤️,” Mann captioned a few photos on Instagram.
December 21, 2022: Judd Apatow celebrates 10 years ofThis Is 40with photos of Leslie Mann and their kids
March 12, 2023: Judd Apatow and Leslie Mann attend theVanity FairOscars party
Jon Kopaloff/Getty Images for Vanity Fair
“Date night ❤️,” theThis Is 40star captioned a series of images onInstagram, including snapshots of her and Apatow mingling with their daughterIris Apatow,Olivia Rodrigo,Vanessa HudgensandRita Ora.
May 14, 2023: Judd Apatow celebrates Leslie Mann on Mother’s Day
Judd Apatow Instagram
In honor of Mother’s Day, Apatow gave Mann a sweet shout-out onInstagram.
“Maude and Iris are so blessed to have a mom like you. You are the greatest mom - so devoted and loving, wise and fun,” he wrote. “There is nothing you wouldn’t do for them and there is nothing we wouldn’t do for you. We all love you so much and treasure you.”
source: people.com
