Jason Biggs and Jenny Mollen's Relationship Timeline: What to Know Following Their Split After 18 Years of Marriage

Jason Biggs and Jenny Mollen are going their separate ways.

The now-estranged couple's romance began when they met on the set of the 2008 movie My Best Friend's Girl in 2007. According to Mollen, she met her future husband on Friday the 13th.

"[The meeting happened] right after he walked under a ladder and ran over a black cat," she joked during an appearance on a 2023 episode of Live With Kelly and Ryan.

They later went on a blind date, though the twosome almost did not work together in the film after Mollen tried to encourage a producer to cast someone else since she thought Biggs was already successful.

"I, of course, was like, 'Well, who cares about Jason Biggs? He's already famous. You have to give it to the underdog,'" she told Access Hollywood in 2022.

The Crash star added, "I didn't want to root for Jason. He already had more than I had. I was already jealous of him without even knowing him. So, I pushed the other guy and then I watched the tapes and instantly had to call the producer back and say, 'I'm blown away. Jason Biggs is a really good actor. You have to give it to him — and I might be in love with him.'"

After their relationship quickly grew serious, Biggs proposed to Mollen in January 2008.

Biggs and Mollen exchanged vows in front of about 40 guests during a private sunset ceremony in Napa, Calif.

The Girls actress shared more details about the nuptials in an April 2022 Instagram post celebrating their wedding anniversary.

"14 years ago, two people who'd known each other for only 9 months drove to a Calabasas FedEx Kinkos in their pajamas and got married," she wrote. “Who knows if that FedEx was even real or a figment of our imaginations or if the woman who married us was a licensed justice of the peace or just some down-on-her-luck actress looking to make a quick 300 bucks."

Mollen added, "We may never know if our union is truly recognized by the state of California or if what happened that Earth Day wasn't just some psychedelic mushroom trip, but what has come out of it has been mind-bending, life-altering, and nothing short of a miracle."

But behind their seemingly picture-perfect marriage, the American Pie actor admitted he was still struggling with addiction at the time.

"I had a couple years there where, even though I had gotten married and ostensibly was maturing and becoming this adult, I was still just blocking everything out with drugs and alcohol," he shared on the "Well With Arielle Lorre" podcast in 2025. "Just everything was still kind of a blur, and it just sort of got worse and worse."

Things changed for Biggs when he learned Mollen was pregnant with their eldest son, Sid.

"'I just found out my wife is pregnant, and what was my reaction? I did every drug I could find. Like, that's not sustainable. It can't be. I don't want to be that,'" he said, later realizing he had to make a change.

They welcomed their first child on February 15, 2014.

While navigating their marriage, Biggs and Mollen also continued working together, including in the 2016 comedy Amateur Night and the 2024 reboot of Dinner and a Movie.

"It's always tricky working with your spouse because he's going to say things to me that he would never say to another actress or cohost, [he] just couldn't get away with it," she told Us Weekly in November 2024, while Biggs responded, "Like what? 'Show me your b----?'"

The Angel alum continued, "'Show me your b----.' 'Suck my d---.' I'm just kidding. But you can say to your wife, 'No, Jenny, don't do it that way,' and it can be helpful. … It is more casual, which can be amazing, but it can also lead to a lot of couples' therapy sessions."

Biggs and Mollen welcomed their second child, Lazlo, on October 2, 2017 — the same year the Anything Else actor got sober.

"He's actually a really good baby," Biggs said of baby No. 2 in a November 2017 interview. "We'll literally go hours and we'll be like, 'Have you changed him?' … 'No, I haven't changed him. Have you changed him? Should we check his diaper?' We check his diaper and there's like a blowout. We're like this poor kid has been sitting in a pile of his own s--- for the last – how long?!"

The now-estranged couple made what would become their final appearance together as a couple at the 43rd Torino Film Festival in Italy in November 2025.

In a statement, a representative for Biggs and Mollen confirmed they had separated but did not disclose the reason for their split.

"They are on great terms and remain focused on raising their two boys," the representative added.

A source also told People they "are doing great" despite ending their marriage.

"They are very much connected," said the insider. "I have no doubt that they will remain on excellent terms."