Leslie Mann and Judd Apatow's Relationship Timeline

In 1995, Judd Apatow met Leslie Mann at an audition for his film The Cable Guy and it didn't take him long to fall hard for the actress. After some persistence, Apatow convinced Mann to join him for a night out at a basketball game and by the next morning, they were both in love.

"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," Mann recalled 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 for The Cable Guy

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 told ELLE.

Meanwhile, Mann says the "nerve-racking" audition had her "in a panic" and she only remembers thinking that director Ben Stiller was 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

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 film Knocked Up

In 2007, the couple got the chance to work together again when Apatow directed Mann in his hit comedy Knocked 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.

"I didn't want to put them in the movie, but Judd, he thought that it was a good idea. Time passed by, and I was saying no, no. no, and then I'm like — I dunno, maybe. And then it was like a week before and he said, you have to tell me now. He would ask me when I was really busy, so I couldn't really focus on it and then it ended up just happening. But it's okay," Mann told Collider.

2008: Judd Apatow casts Leslie Mann in Drillbit Taylor

The following year, Mann and Apatow continued their streak of working together when Mann appeared in Drillbit Taylor. In the flick, based on an original story by John Hughes, Mann played Lisa, a teacher who has a relationship with Drillbit.

December 2012: Leslie Mann reprises her role in Knocked Up sequel This Is 40

The couple got the chance to work together again on the Knocked Up sequel, This Is 40. The film focused on the relationship between Mann's character and her on-screen husband Paul Rudd — and sometimes it hit a little too close to home. Mann admitted that her real-life arguments with Apatow inspired the film's script but by the time the movie hit theaters, it had lost its personal connection.

"Sometimes we would have arguments through the characters — things we were afraid to say to each other. But by the time it winds up in the film, it isn't at all what we're like … I don't know, it doesn't feel to me at all autobiographical," Mann told The Guardian.

March 2013: Judd Apatow opens up about his 17-year marriage with Leslie Mann

Following the release of This Is 40, Apatow shared the key to making his marriage with Mann work. He explained that not only do they like working together and "get along much better than one would assume during the creative process," he also noted that they were always aiming to understand one another.

"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 pair celebrated 20 years of marriage and 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 on The 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 Apatow made their TikTok debut on their daughter Iris' account in November 2019. In the video, Iris introduced her family while lip-syncing along to a song from Teen 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

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 finished The Crown season three without me, and Barry season two and The Liar on @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 finish The Sinner season three and the current Narcos season without me. ❤️❤️," Apatow wrote alongside a photo of 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 with Rolling 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?" Mann joked on Live With Kelly and Ryan.

April 2022: Leslie Mann stars in Judd Apatow's film The Bubble alongside their daughter Iris

In 2022, Mann once again worked alongside her husband in their movie The Bubble, which premiered on Netflix in April. The film centered around a cast and crew trying to film a sequel to an action franchise about flying dinosaurs amid the COVID-19 pandemic. Not only did Mann have a starring role in the film, but she was also joined on-screen by her daughter Iris, who fittingly played an outgoing young actress.

June 13, 2022: Leslie Mann and Judd Apatow celebrate 25 years of marriage with their daughters

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 a series of photos on 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 iconic Diana Ross perform, 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 of This Is 40 with photos of Leslie Mann and their kids

Apatow marked the 10-year anniversary of his comedy This Is 40, which starred Mann and their daughters, by sharing photos behind-the-scenes photos on Instagram. His carousel post also included sweet snaps of himself directing both Mann and Iris on set.

March 12, 2023: Judd Apatow and Leslie Mann attend the Vanity Fair Oscars party

Before heading inside the Vanity Fair party, the couple posed for a few photos on the red carpet. Mann dazzled in a black tulle gown by Oscar de la Renta, while Apatow looked handsome in a black tuxedo.

"Date night ❤️," the This Is 40 star captioned a series of images on Instagram, including snapshots of her and Apatow mingling with their daughter Iris Apatow, Olivia Rodrigo, Vanessa Hudgens and Rita Ora.

May 14, 2023: Judd Apatow celebrates Leslie Mann on Mother's Day

In honor of Mother's Day, Apatow gave Mann a sweet shout-out on Instagram.

"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."