Olivia Munn and John Mulaney's Relationship Timeline: Love and Parenthood

John Mulaney and Olivia Munn kicked their romance into high gear after his split from his wife of six years, Anna Marie Tendler, in May 2021. As news broke that Mulaney and Tendler had called it quits, Us Weekly confirmed that the comedian had moved on with Munn. Mulaney and Munn were photographed on a date together in Los Angeles in June 2021, and a source told Us that the actress was “on cloud nine” as the twosome grew closer. “John thinks Olivia is really smart and she makes him laugh too,” the insider added. The couple welcomed their first child, son Malcolm, in November 2021. “She and John are both very in love with their baby boy,” a source exclusively told Us of the pair in January 2022. “All seems to be going great with John. … It's an exciting time.” In July 2024, the duo once again surprised fans when they quietly tied the knot after three years together. Several months later, they welcomed daughter Méi via surrogate. Scroll down to see how Munn and Mulaney’s relationship has grown:

Munn reflected on meeting Mulaney and Tendler at an event, joking that "he never emailed back" when she tried to keep in touch with him. She told HuffPost Live, "I might’ve got the wrong email — probably. That's what I tell myself."

Mulaney sought treatment for alcoholism and cocaine addiction after 15 years of sobriety, checking himself into a 60-day program in Pennsylvania and completing his stay in February 2021.

At the time, Munn showed her support for the Big Mouth star, tweeting, "Sending SO MUCH love and support to John Mulaney. You got this."

Us confirmed that Mulaney and Munn were dating after his split from Tendler.

"Olivia and John are going strong," an insider told Us about the duo in June 2021. "She has been sneaking into some of his shows and loves them. ... Olivia is so smitten."

The source added that Mulaney and Munn have connected over sharing a "very dry sense of humor."

The pair were spotted together for the first time on a lunch date in Los Angeles. Mulaney and Munn seemed very happy while they dined at Rick’s Drive In & Out.

During an appearance on Late Night With Seth Meyers, Mulaney announced that he was expecting a child with Munn after they connected earlier that year.

"Then in the spring I went to Los Angeles and met and started to date a wonderful woman named Olivia,” he said in September 2021. "And we're having a baby together. I was nervous when I was about to say the news!"

As the comedian reflected on his eventful year, he mentioned how this new chapter of his life would only be that much better.

"Olivia and this baby have helped save me from myself in this early journey out of recovery," he added at the time.

Three days after Mulaney’s reveal, Munn told Access that she was feeling “good” ahead of their baby’s arrival. “Just the outpouring of love and support has been really amazing,” she gushed. "There has been a really big mom tribe that comes up. I’ve heard about it, but they really come up in full force. There’s a really great dad tribe too, everyone comes up is really supportive and it means so much to me.”

Not long after his public declaration of love for Munn, a source told Us in October 2021 that the twosome’s romance has been “imperfect” since the start.

“Even though Olivia’s going to be a wonderful mother and has great support behind her, Olivia’s friends just don’t see these two being a couple in a year’s time,” the source said. “Olivia and John still have to decide what kind of future they’re going to have together, if any. It’s a time of uncertainty, for both of them.”

Another insider added that the same month that Mulaney is a “work in progress” as Munn focuses on motherhood. “Becoming a mom was always more important to her than settling down in a conventional way,” the second source said. “She's a real feminist and doesn't need a man by her side 24/7. She never has.”

“Meet Malcolm Hiệp Mulaney. He has his whole life ahead of him. He hasn’t even tried seltzer yet,” the Comeback Kid comedian captioned a December 24 Instagram snap. “I’m very in love with him and his whole deal. Happy Holidays.”

Following the birth of their son, a source exclusively told Us that the major milestone brought the couple closer together.

“She and John are both very in love with their baby boy,” the insider shared. “All seems to be going great with John. She's usually more private about her relationship but now she's sharing more pics. It's an exciting time.”

During his SNL hosting gig, Mulaney reflected on the birth of his first child with Munn.

"We were in the delivery room. My girlfriend had just given birth to him and he's crying a little, so they bring him over to this warmer on the other side of the delivery room, and they put them on the warmer under this big bright light and light is just shining in his eyes," he detailed in his opening monologue. "He just looks up at the light and [he squints]. He was annoyed, but he didn't say anything. I was like, 'That's my son.' A polite man in an uncomfortable situation, but he's not going to make a fuss. He’s a very good boy.”

At the time, Mulaney noted that he was "happier now" and that life was "a lot better" for him.

"Happy Mother's Day Olivia," the Broadway vet wrote in an Instagram Story on Munn's first Mother's Day, sharing a throwback photo from the day Malcolm was born. "Thank you for the greatest gift in the world."

Mulaney shared a second photo of their baby boy, writing, "Malcolm loves you so much. He told me. Last week."

Days after holding hands on a stroll through New York City, the two were spotted on another outing in the Big Apple.

“Olivia’s truly been his rock post-rehab and is super supportive of him,” a source exclusively told Us Weekly about the couple in June 2022. “Being a father has certainly changed his perspective on life in that he realizes he has another human to take care of so he wants to be the best dad he can be and just be healthy and present for him."

While the pair are enjoying life as new parents, the insider noted that they were "not in a rush to get married. It's definitely not her focus right now. She really wants to enjoy this time as a new mom." The source said at the time: "Olivia's fully embracing motherhood and all its challenges and ups and downs."

Munn had a surprise for Mulaney's 40th birthday during his Nashville, Tennessee, show. "Malcolm surprised John on stage last night to sing HBD with the whole audience," Munn revealed via her Instagram story one day later. 

Munn gave a glimpse at her NYE with Mulaney via an elevator selfie.

"When the platform heels came off," she captioned the snap at the end of the night.

"You made me a dad, Olivia. I love you forever for doing that," Mulaney captioned an Instagram photo of him and Munn with their baby boy in honor of Father's Day.

The couple were all smiles as they held hands on a rare night out in L.A.

Munn celebrated Mulaney's Emmy win for his Netflix special Baby J, sharing a series of Instagram pics from the big night. "Thank you baby! What a sharp, unsafe thing to bring home!" Mulaney teased in the comments section.

Munn shared via Instagram that she was diagnosed with breast cancer in February 2023 and underwent a double mastectomy amid treatment. After freezing her eggs, Munn revealed she had a full hysterectomy. Throughout the process, the actress had Mulaney to lean on.

“I’m so thankful to my friends and family for loving me through this. I’m so thankful to John for the nights he spent researching what every operation and medication meant and what side effects and recovery I could expect,” Munn wrote via social media after going public with her health battle. “For being there before I went into each surgery and being there when I woke up, always placing framed photos of our little boy Malcolm so it would be the first thing I saw when I opened my eyes.”

In response, Mulaney commented, “Thank you for fighting so hard to be here for us. Malc and I adore you. ❤️”

A source exclusively told Us the same month that Mulaney was a “huge pillar of strength” for Munn throughout her cancer scare.

The pair tied the knot in a quiet ceremony over the 4th of July weekend at a friend’s home in New York, according to People. Mulaney and Munn’s son and a witness were reportedly the only ones in attendance.

“I got married,” Mulaney confirmed during an appearance on Late Night With Seth Meyers. “Thanks a lot. It’s the best.” The comedian gushed over the milestone, calling it, “The greatest single time in my life.”

Their second child, daughter Méi, was born on September 14 via surrogate.

“I had so many profound emotions about not being able to carry my daughter. When I first met our gestational surrogate we spoke mother to mother,” Munn, who previously had a hysterectomy following her breast cancer battle, wrote via Instagram. “She showed me so much grace and understanding, I knew I had found a real-life angel. Words cannot express my gratitude that she kept our baby safe for 9 months and made our dreams come true.”

While appearing at a gala celebrating the Broadway opening night of All In: Comedy About Love at The Hudson Theatre on December 16, Mulaney lovingly kissed his wife Munn’s hand.

Munn was spotted sitting next to her husband in the SNL 50: The Anniversary Special crowd. The couple were also photographed holding hands later in the evening as they attended the afterparty at NYC’s Plaza Hotel.

Munn gushed over seeing a softer side of Mulaney after they became parents. 

“I really had no idea what kind of a father he would be, what kind of a friend he would be to me ... but the day Malcolm was born, John’s whole world just lit up,” she told People in June 2025. “And Malcolm looks just like John. He just changed his whole little life. Not to be too saccharine, but looking at John looking at Malcolm, I could see all that healing happening.”

The actress said that Mulaney made “health a priority" when Malcolm was born. 

"He started working out with trainers and eating really healthy. And gosh, I mean, the guy has protein powder in the house,” Munn revealed. 

She continued: “He talks about intermittent fasting, he's got a sauna and a cold plunge. That little boy came into his life and just swept him off his feet. Now he's doing everything he can to live the healthiest, best life."

Munn could not help but post an adorable glimpse of parenthood via Instagram on her 45th birthday. 

“Made it to Level 45!!! So lucky I got here. 🎂♥️✨,” she captioned a photo holding her daughter. 

In a second slide, Munn shared an adorable voice recording asking her son what day it was. “Mama’s birthday,” he sweetly replied. 

When she asked if he wanted to wish her a happy birthday, he responded, “No,” which made Munn laugh.