The Weirdest Things About John Mulaney And Olivia Munn's Relationship

John Mulaney and Olivia Munn's controversial relationship got off to a rocky start, to say the least. Fresh off his separation from artist Anna Marie Tendler in 2021, the comedian immediately moved on with the actress, raising eyebrows everywhere and sparking a lot of questions about the timeline of their relationship. However, Mulaney and Munn weathered the cheating rumors, intense public backlash, and a battle with breast cancer together and appeared to have come out on the other side stronger. They've since tied the knot, welcomed two children together, and gushed about each other on social media and in interviews, proving they're still going strong.

Munn was top of mind for Mulaney at the GQ Men of the Year party in November 2024, telling "Access Hollywood" on the red carpet: "We're especially thrilled this week because [Olivia] is on the cover of Time, and we're so proud of her." In the previous month, Mulaney also paid tribute to his wife and highlighted the massive "increase in women visiting the breast cancer risk assessment" after Munn went public with her cancer diagnosis and double mastectomy. "Olivia saving lives by speaking her truth is not surprising to me," the stand-up comic said while presenting her with the Woman of Impact Award at InStyle's Imagemaker Awards.

But while the pandemic-period uproar over them dating now "feels very distant" to the former "Saturday Night Live" writer, as he told GQ, that doesn't mean people no longer have questions about Mulaney and Munn. From the random drug testing to Mulaney's seemingly overnight transformation from a child-free advocate to a family man, here are the weirdest things about the couple's relationship.

While John Mulaney and Olivia Munn didn't start dating until 2021, their story goes all the way back to 2013 — when they first met at a wedding. The "X-Men: Apocalypse" actress told HuffPost Live in 2015 that she repeatedly tried to strike up a conversation with the comedian throughout the event, admitting, "At first, it was cool and then I kept going up to him at the wedding like, 'So you having fun?' I was just so obsessed with hanging out with and talking with him."

However, at the time, Munn was dating actor Joel Kinnaman and Mulaney was already engaged to Anna Marie Tendler, with whom he tied the knot in July 2014. Munn was aware he was taken as she said she had asked Mulaney if he and Tendler would "want to go have dinner or something and go hang out" with her sometime. Munn was apparently so determined to develop a friendship with him that she even asked a friend for Mulaney's email address and reached out to him following the nuptials. But whether it was intentional or not, Mulaney seemingly made his thoughts about her invitation clear by not responding to Munn's email. However, Munn told the outlet that Mulaney might not have intended to leave her on read, adding: "I might've got the wrong email — probably. That's what I tell myself."

While the "Predator" actress emphasized that she was simply fangirling over Mulaney at the time, the actions she described seemed like those of someone hitting on their crush rather than a fan meeting their favorite comedian.

Fans went wild back in September 2021 when John Mulaney shared the exciting family news on "Late Night with Seth Meyers" that his then-new girlfriend Olivia Munn was pregnant. Aside from the fact that he and Anna Marie Tendler hadn't even finalized their divorce yet and that he and Munn had gone public with their romance just three months prior, Mulaney had repeatedly made it clear that he didn't want kids of his own. "They're great, but I love what I do. And I love my wife and spending so much time with her and we have a really fortunate life. I get to travel, do stand-up, and our relationship is so wonderful. It's just something I wouldn't want to change," he told Entertainment Weekly of his child-free stance in 2019.

But as Mulaney's subsequent actions have shown, he was apparently not as happy in his marriage to Tendler nor as against having kids as he made himself out to be. Just a few months after filing for divorce from Tendler, the comedian was gushing to Meyers about how much he was looking forward to being a dad to his and Munn's first child together. He even credited the actress and their then-unborn child with motivating him to stay sober after he relapsed in his struggle with drug addiction. "I'm gonna be a dad ... we're both really, really happy," Mulaney said, adding: "Olivia and this baby have helped save me from myself in this early journey out of recovery."

Munn and Mulaney's two kids, son Malcolm and daughter Méi, have since made multiple appearances on the comedian's Instagram. On Father's Day 2023, he shared photos with Munn and Malcolm and wrote: "You made me a dad, Olivia. I love you forever for doing that."

In his interview with Seth Meyers, John Mulaney said he and Olivia Munn reconnected in spring 2021 and "started to date" shortly after — while indirectly confirming that he and Anna Marie Tendler were already separated at the time. Just months later, in November, People reported that Mulaney and Munn welcomed their first child, Malcolm, which suggested that the actress got pregnant around March or April. This had fans speculating that the pair fell in love and got serious in a matter of days (if the timeline is accurate), but in reality, love came much later than the pregnancy part did.

According to Mulaney's cover story for GQ's Men of the Year 2024 issue, his and Munn's relationship began as a quick fling between two people who weren't expecting anything long-term. However, that fling ended up leaving Munn pregnant with the baby of a fellow celebrity she wasn't in a relationship with. The actress explained to the magazine that her and the comedian's relationship "wasn't anything close to 'dating'" when they found out they were expecting a child together, adding: "I barely knew him." The pair initially decided to move forward as co-parents and spent most of Munn's pregnancy apart, with Mulaney visiting her or calling her whenever he could. "It wasn't necessarily 'We're going to be married and live together' or any of that, but it was 'I will be involved in some way,'" Munn explained.

However, around September 2021, two months before Malcolm's arrival, Mulaney's and Munn's relationship transformed from co-parenting to a full-blown serious romance. By February 2022, Mulaney was publicly referring to her as "my girlfriend." The pair later tied the knot in July 2024.

Many stars, including John Mulaney, have opened up about their addiction issues, but it's rare for a celebrity couple to be as candid as the comedian and Olivia Munn have been about the realities of living with a partner and co-parent who's on a sobriety journey. Mulaney, who struggled with an addiction to alcohol, prescription drugs, and cocaine, entered a rehab facility in December 2020. However, after he finished his treatment, he relapsed and chose to go back (after his close friends staged an intervention). The comedian had been fresh out of his second consecutive stay in rehab in early 2021 when he began his dalliance with Munn and got her pregnant.

While they weren't officially a couple yet, a then-pregnant Munn volunteered to take an active role in Mulaney's recovery after he privately admitted his fears of falling off the wagon again, according to GQ. The method they decided on was that the actress would give him random drug tests.

Mulaney, who has been sober since his last rehab stint, said that Munn never stopped giving him these tests and that they've been a big help in his sobriety journey. "It's like a relief," he told the magazine. "I like to be able to not even have that be a question in her or anyone else's mind. Something about peeing in that cup is like, I'm walking this walk. It gives me confidence."

When John Mulaney married Olivia Munn, he didn't just gain a wife — he also gained many new family members. During an August 2024 appearance on Seth Meyers' show, Mulaney was all praise for his in-laws, saying, "Marrying into a large Vietnamese family is one of the most fun things I've ever done." Munn, who was born to a German-Irish father and Vietnamese mother, told GQ that her mom and aunts welcomed Mulaney into the fold very quickly because of their shared interests, which apparently include gossiping about the other members of the family. "John has seamlessly fit in with my mom and aunts in a way that I have never been able to. They love the same movies. They love the same Vietnamese gossip," the actress shared.

Mulaney noted that part of the charm was how different Munn's family was from his own. According to the comedian, Munn's family members were much more open with each other to the point that it seemed nothing was off-limits when it came to topic conversations. "My family is white, Caucasian... so we're uptight about a lot of topics. Money, health, anything — almost everything is taboo," he told Meyers. "The Luong family, they talk about anything immediately upon meeting you. 'How much money you have? Why you so skinny?'"