A deep dive into Anna Kendrick's complete dating history

As star and director of Woman of the hourAnna Kendrick tells the true story of one dating game Contestant who unwittingly chooses a bachelor with a very twisted story. It's a thrillingly dark depiction of dating and its evolution over time, and it's exactly the kind of in-depth exploration that Kendrick doesn't do about her own dating life.

Over the years, Kendrick has kept quiet about their romances, mostly only revealing a few tidbits here and there. “Well, when it comes to privacy, it's not easy, as you're proving right now,” she said The Sydney Morning Herald in 2020. “But that’s just how it’s always been for me.”

Kendrick has been linked to a number of Hollywood stars, from Bill Hader to English filmmaker Edgar Wright. And while she will never name names, she has also been open about a toxic ex-partner in the past.

When visiting the Armchair expert On her podcast in 2023, Kendrick said she knows what it's like to date an abusive partner. “That was someone I lived with,” Kendrick told the hosts, saying her ex seemed to change in an instant. “I remember telling my brother when things first broke down, 'I'm living with a stranger.' I don't know what's happening.'”

But despite a complicated history, Kendrick remains friends with many of her exes and currently appears to be single. She recently said whether she would ever want to have children The Guardian: “I thought, 'With the weight of a cat, I would fall asleep easier.' But I'm not responsible enough to own a cat. “Someone should really build a robot cat that does all the purring and kneading.” And then I thought, wait, I’m not even up to the “cat lady” part yet! Why would anyone trust me with one? child?” That seems to clear it up.

Ahead, take a deep dive into Anna Kendrick's complete dating story.

Bill Hader (2020–2022)

Just like Kendrick, Hader likes to keep the details of his relationships private, and news of their connection came over a year after they began dating – at least according to a report from People.

In January 2022, the outlet shared the following: “Anna has been quietly dating Bill for over a year. They met years ago. She is the hostess Saturday Night Live and they did a movie together, but they didn't get together until long after the movie.” (The movie in question was the Disney Christmas movie Noellewhich came out in 2019.)

After playing siblings Noelle and Nick Kringle on screen, the two bonded on another level, and the COVID-19 pandemic apparently helped them keep things under wraps. “They are both very private people, and given the pandemic, it was easy to maintain silence,” the source added. “They are both hysterical and constantly have to make each other laugh.”

After years of being strong, it was reported in June 2022 that the two had broken up.

Ben Richardson (2014–2019)

Celebrity sightings in New York City, August 14, 2015

Alo Ceballos//Getty Images

Kendrick met Richardson for the first time on set Drinking friendswhich they filmed together in the summer of 2012, but it is believed they only started dating in 2014.

The following year, the couple was spotted together in New York's SoHo neighborhood, where Kendrick appeared to be wearing an engagement ring.

As noted by the Daily Mail Back then, Kendrick had worn the same ring on a different finger during a Hawaii vacation with Richardson the month before. This either suggested that Richardson had proposed and they had to wait for the ring to be resized, or that Kendrick was simply trying something out.

The latter seems to be the case considering Kendrick dismissed engagement rumors in an interview with Marie Claire the following month. “No, it's not even a diamond ring!” she told the outlet with a laugh. “(It’s) costume jewelry!”

While it's unclear when they stopped dating, Entertainment tonight reported that Kendrick and Richardson were last seen together in 2019.

Jake Gyllenhaal (2013)

While a relationship between Kendrick and Gyllenhaal was never confirmed, there were rumors about the couple's relationship after they played an on-screen couple in the police thriller End of watch (2012).

The two seemed to have undeniable chemistry, as Mario Lopez noted in a September 2012 interview with Kendrick. “He’s a great kisser. He's a real gentleman,” she said when asked about their on-screen smooches. She also added that Gyllenhaal was completely shaved for the role, but grew some more hair for his latest project. “I like the scruffy Jake,” she added.

In 2014, Kendrick expressed her frustration when Gyllenhaal dropped out of the live-action remake of Into the forest. “I was so mad at Jake, I can tell you that,” Kendrick said in an interview with The Daily Beast. “I texted him and said, 'You're leaving me and I'll never forgive you!' And then I watched the trailer for it Nightcrawler and texted him again and said, 'Wow, you inspire me every day.'”

Edgar Wright (2009–2013)

“Scott Pilger vs. The World” director Edgar Wright poses at the beginning of the film

Boston Globe//Getty Images

Kendrick and Wright first met on the set of Scott Pilgrim vs. the Worldin which Kendrick played the title character's sister, while Wright served as director and producer. Before working together, Kendrick was already a fan of the director, as she revealed in an interview Vanity Fair Video interview in 2023.

“I'll be honest, when I first read this script I thought, 'I don't quite understand this.' But I love Shaun of the DeadI love Hot fuzz.' And I just wanted to work with Edgar Wright,” she said. “But I remember on paper it said, 'I don't know how this is going to work, but I'm just trusting he'll see it' – which he did. It’s so great.”

Although it is unclear exactly when their relationship began, Us weekly reports that it was shortly after meeting on set. The two Hollywood stars stayed together for the next four years and separated amicably in 2013.

Since then, things seem to continue to be friendly between them, at least based on some of their public interactions on social media. Kendrick also confirmed their continued friendship on an episode of Armchair expert in 2023.

Bill Hader (2020–2022)

Ben Richardson (2014–2019)

Jake Gyllenhaal (2013)

Edgar Wright (2009–2013)

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