Inside Olivia Munn and John Mulaney's Whirlwind Romance

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News broke that Olivia Munn and John Mulaney were dating in May and they're now expecting a baby, but the 41-year-old actress had made no secret about her admiration for the 39-year-old comedian in the past. Let's take a deeper look into their surprising romance.

Back in January 2015, Munn talked about being a big fan of the former Saturday Night Live writer and her encounter with him and his then-fiancèe, 36-year-old Anna Marie Tendler, at a wedding. The wedding appears to have been Seth Meyers and Alexi Ashe's wedding in 2013. Mulaney wrote an article for Vogue on his fellow SNL star's nuptials, which took place on Martha's Vineyard, and Munn appears in the first photo.

"We were at a wedding together and I was like 'Oh my gosh, do you and your fiancèe want to go have dinner or something and go hang out?'" Munn told HuffPost Live back in 2015 of her interaction with Mulaney. "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."

She said she later sent him an email but he never replied. 

"I might've got the wrong email -- probably," she cracked. "That's what I tell myself."

Mulaney and Tendler, a makeup artist, got married in July 2014 in New York. It appears Munn -- who dated Green Bay Packers quarterback Aaron Rodgers for three years before they split in 2017 -- and Mulaney remained friends over the years, as she supported him when he checked himself into rehab for addiction issues last year. Mulaney has been open about struggling with alcohol and cocaine addiction in the past, telling Esquire magazine in 2019 that he began drinking at the age of 13 "for attention," and that he battled addiction in his teens and in his twenties.

Munn tweeted last December on the day the news broke of Mulaney entering rehab, "Sending SO MUCH love and support to John Mulaney. You got this. ❤️⚡️."

Following his 60-day stint in rehab, Mulaney and Tendler split. Page Six reported on the split in May, with sources telling the outlet that he had asked for a divorce three months prior. In a statement, Tendler said it was Mulaney who decided to divorce after six years of marriage.

"I am heartbroken that John has decided to end our marriage," she said. "I wish him support and success as he continues his recovery."

Just days later, multiple outlets reported that Mulaney was now dating Munn.

"This is very new, they're taking it slowly," a source told People of their romance.

In June, Munn and Mulaney were photographed on a lunch date in Los Angeles together, appearing in good spirits. Mulaney officially filed for divorce from Tendler in July. 

John Mulaney and Olivia Munn
Michael Simon/Shutterstock

In a full-circle moment, Mulaney broke the news that they were expecting a baby on Meyers' late-night show on Tuesday. Mulaney talked about his tough time in rehab and moving out of his home with Tendler, and then dating Munn.

"Then in the spring I went to Los Angeles and met and started to date a wonderful woman named Olivia," he said. "I got into this relationship that's been really beautiful with someone incredible. She held my hand through that hell, and um, we are having a baby, together."

"I'm gonna be a dad!" Mulaney added as Meyers congratulated him. "I'm really -- we're both really, really happy."

Interestingly enough, Mulaney famously joked about not wanting children in his 2015 standup special, The Comeback Kid. Mulaney said he and Tendler felt constant pressure to have kids, including from their real estate agent.

"Our real estate agent wanted us to have a baby more than anyone else in our lives. More than anyone else in our family," he said. "She hinted about it constantly. Every room we'd walk into, she’d be like, 'So this could be an office, or maybe a nursery.'"

Although he said he and Tendler would tell her they didn't plan on having kids, she responded, "You don't know if you're gonna have [kids], but you know, you never know. Sometimes you don't know what’s gonna happen and then, you know, something happens."

Meanwhile, back in 2016, Munn told Anna Faris on her Anna Faris Is Unqualified podcast that she had frozen her eggs years ago.

"I turned 35, then you're high risk," she explained. "It's no longer on the experimental list and I think that every girl should do it. For one, you don't have to race the clock anymore. You don't have to worry about it, worry about your job or anything. It's there. It's also just like, why not do it, because I see so many women who go through this. Doomsday is now like whatevers day, because I am prepared."

When ET spoke with Munn in 2019, she opened up about her outlook on kids and marriage. At the time, she was dating Philadelphia Fusion president Tucker Roberts, but they split last August.

"I have two dogs, two cats, so that's a lot just with the animals. I don't have kids," she said. "I mean, honestly it's a lot. I can't imagine. I've really come to a realization with myself that I'm already in my happily ever after. And if I want to have kids or want to get married then I'll do that, but it has to add to my life, you know? Everything has to add to my life."

"I already love my life as it is," she continued. "I'm excited about anything that might come my way, but I've already reached the pinnacle for me, what I think happiness should look like. I've got amazing girlfriends. I've got my pets. I've got my career. I'm really, really happy. Anything else that wants to come into my life has to add."

ET recently spoke with Munn about her new film, The Gateway, in which she plays a single mother. She acknowledged that one thing she struggles with being in Hollywood is "perception versus reality" when it comes to what some people think about her.

"There's a lot of people who see you one way and no matter how much good you try to do in the world, or no matter who you are or what your friends know of you, there is a perception that is put onto you and that does become your reality in some ways," she said. " ... But when you have a really strong sense of self, you really try to lean on that, allow that to take over and any doubt that is cast on you from anything in the world."

"Sometimes when people say too many good things about you, you feel like you can't live up to that too," she added. "Just being in this business in general, it's not for the faint of heart."

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