Anna Kendrick, Rachel Bilson, More

When a comedian gets serious. Bill Hader has kept his personal life relatively quiet over the years, but he’s been linked to a series of famous women since he rose to fame on Saturday Night Live.

Shortly after the Oklahoma native joined the NBC sketch comedy series in 2005, he wed Maggie Carey, whom he met through mutual friends. The Barry star and the A.P. Bio writer tied the knot in 2006 and later welcomed three daughters: Hannah (born in 2009), Harper (born in 2012), and Hayley (born in 2014).

Throughout their marriage, Hader and Carey collaborated on a handful of projects, most notably the 2013 film The To Do List, which Carey wrote and directed. The comedy starred Aubrey Plaza as a young woman named Brandy Klark who wants to lose her virginity after graduating from high school.

“There’s a lot of shorthand,” the Skeleton Twins actor told USA Today in 2013, explaining how he and his then-wife worked well together. “My memories of shooting the movie are more of going and picking her up and taking her to work. She could barely walk by then [from exhaustion].”

He added that he worried about whether he’d be able to fulfill her vision for the project, in which he played Brandy’s boss, Willy. “If it was me directing the movie, I wouldn’t have cared as much, but because it was my wife, I was very protective,” Hader explained. “It was kind of like having our own party.”

Four years later, however, the duo called it quits, with Hader filing for divorce in December 2017. The former couple have never publicly spoken about what led to their split, but the Emmy winner has been open about how difficult it was to balance his family life with his career while he worked on SNL.

“When I was on SNL, I was a bit of a basket case,” Hader told Variety in 2019, noting that he suffered from panic attacks and migraines. “It could not have been easy on my wife at the time. I was so consumed with work and anxiety. Sometimes I felt like people thought, ‘Oh, he’s just wanting attention or something.’ It was like, ‘No, man, I’m legit. I’m freaking out right now.’”

After the pair welcomed their second child in 2012, the Pineapple Express star decided to leave SNL, with his final episode airing in May 2013. He’s since returned to host the show multiple times, reprising some of his most famous characters (including Stefon).

“It was hard with one kid, let alone two,” Hader told Variety. “Because I was just never around.”

After his split from Carey, Hader moved on with Rachel Bilson, who appeared in The To Do List. The duo made their red carpet debut at the Golden Globes in January 2020 but called it quits later that year amid the coronavirus pandemic.

The O.C. alum later said that the breakup hit her extra hard because it occurred during the lockdown period when many people could not leave their homes. “All breakups are hard,” Bilson explained during an August 2022 interview on the “Call Her Daddy” podcast. “Things happen, things change. There was a pandemic. Yeah, so it was a hard time.”

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Keep scrolling for a look back at Hader’s dating history: