Bill Hader's Dating History: From Rachel Bilson to Anna Kendrick

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Over the years, Barry actor Bill Hader has been linked to a few leading ladies, most notably, some of his previous costars.

Hader was previously married to filmmaker Maggie Carey from 2006 to 2017, with whom he shares three children.

Though the Saturday Night Live alumnus has made headlines for his various romances, he previously told The Hollywood Reporter that he doesn't talk about his dating life publicly to protect his daughters.

"They just want me to be their dad," Hader told the outlet. "They just want me to sit and watch Encanto over and over and over again. So that's what I do."

While Hader has refrained from talking about his relationships, some of his former girlfriends have opened up about dating the star (including his The To Do List costar Rachel Bilson, whom he dated in 2020).

Here's a look back at Hader's dating history.

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Maggie Carey

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Hader first met Maggie Carey, a filmmaker who directed his 2013 film The To Do List, in Los Angeles through one of her friends from college. The two later moved to New York City together when he was cast on Saturday Night Live from 2005 to 2013. The pair married in 2006 and eventually welcomed three children together, daughters Hannah, Harper and Hayley.

In November 2017, PEOPLE confirmed that the couple had been separated since July and were in the process of getting a divorce. The following month, Hader filed court documents citing irreconcilable differences as the cause of the split and seeking joint physical and legal custody of their children, according to court documents obtained by The Blast. In March 2018, the two reached a settlement in their divorce and they were restored to single persons that June.

Following their split, the two have continued to co-parent their children. During an interview with Variety in 2019, Hader broke down in tears as he discussed the challenges of balancing his career with being a dad.

"I think I saw my kids a total of five days all summer. It was terrible," said Hader of his busy schedule. "I'm going, 'Next summer I'm taking off. And I'm going to spend every day with them,' " Hader said of his girls. "It's this weird thing where when you're in this industry, you don't have time to be with them, and it's really, really difficult. I'm getting emotional right now talking about it."

During an interview with The Hollywood Reporter in March 2022, Hader briefly opened up about co-parenting with Carey during the COVID pandemic, noting that he was worried about the impact stress from the period could have on their daughters.

"Maggie and I were just trying to keep them calm," he said. "And then, weirdly, it was the other way around. They would really keep us calm."

Rachel Bilson

Jon Kopaloff/Getty Images Bill Hader and Rachel Bilson

Hader and Rachel Bilson first sparked romance rumors when they were spotted grabbing coffee together in his hometown of Tulsa, Oklahoma, in December 2019. The two had previously worked together on The To Do List, which was directed by his then-wife Carey.

The pair publicly confirmed their relationship when they attended the Golden Globe Awards together on Jan. 4, 2020, holding hands as they made their way down the red carpet.

"They spend a lot of time together and it seems like a serious relationship," a source told PEOPLE that February. "They were in L.A. over the Valentine's Day weekend. On Sunday, they enjoyed a getaway to the Montage Hotel in Laguna Beach."

"It seems like a fun relationship," the source said, adding that Rachel "always seems entertained," around Hader. "She won't stop laughing when she's with Bill. He is very sweet and considerate to her. Quick to open doors and acts very attentive."

However, in July 2020, multiple sources told PEOPLE that the couple amicably split. Bilson seemingly addressed their split during her podcast Broad Ideas in 2022, referring to a breakup that happened during the height of the COVID pandemic.

"I could not leave my house, you know what I mean? I had nothing else to do but sit in it, and deal with it and feel it," Bilson explained. "It was probably the hardest thing I've ever done⁠, harder than childbirth."

In August 2022, Bilson talked about Hader yet again when she was asked what she misses most about her ex. "His big d---," the actress candidly told Tommy Dorfman on an episode of her podcast. "We can keep that [in the final edit]," Bilson doubled down, then added (presumably to her producer): "And cut, let's move on."

Anna Kendrick

Matt Winkelmeyer/Getty Images Anna Kendrick

In January 2022, PEOPLE revealed that Hader was dating Anna Kendrick. The news came after the two played siblings in the 2019 Disney+ holiday film Noelle, in which they played the children of Santa Claus.

"Anna has been dating Bill quietly for over a year," a source told PEOPLE at the time. "They met years ago. She's hosted Saturday Night Live and they've done a movie together, but they got together well after the movie." (Kendrick hosted SNL in 2014, though Hader left the cast in 2013.)

"They are both very private people, and with the pandemic it was easy to keep it quiet," added the source. "They're both hysterical so they must keep each other laughing all of the time. She's really, really happy."

Another source told PEOPLE that Kendrick and Hader were a "great couple" together. "You can see the chemistry when they're together. They have a really fun rapport, very sarcastic and funny but all coming from a place of love," the source said. "You'd think she'd be the one kind of running the show, but she's pretty quiet around him."

"They're affectionate but it's the way they look at one another when the other is talking, you can see they really love each other," the source added.

After nearly two years together, Entertainment Tonight reported that the couple had split in June 2022.

Ali Wong

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In her March 2023 feature with The Hollywood Reporter, the publication noted that the comedian was briefly linked to Hader in 2022, following her divorce from Justin Hakuta, with whom she shares two daughters.

Page Six first reported Wong and Hader's relationship in December 2022, noting that the comedians dated "very briefly" before ending things. "They're just super busy with things, but [the split] was certainly amicable. They're certainly friends," a source told the publication at the time.