A Deep Dive Into Anna Kendrick’s Complete Dating History
As the star and director of Woman of the Hour, Anna Kendrick tells the real-life story of a Dating Game contestant who unwittingly ends up picking a bachelor with a very twisted history. It’s a thrillingly dark portrayal of dating and its evolution over time, and it’s exactly the kind of in-depth exploration that you won’t find Kendrick crafting about her own dating life.
Throughout the years, Kendrick has remained hush-hush about her romances, usually offering only tidbits here and there. 'Well, as far as keeping it private, it isn’t easy, as you are proving right now,' she told The Sydney Morning Herald in 2020. 'But that’s just always how it’s been for me.'
Kendrick has been linked to a number of Hollywood stars, from Bill Hader to English filmmaker Edgar Wright. And while she’ll never name names, she has been open about being with a toxic ex in the past too.
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During a visit to the Armchair Expert podcast in 2023, Kendrick said she knew what it was like to date an abusive partner. 'This was somebody I lived with,' Kendrick told the hosts, saying that her ex seemed to change in an instant. 'I remember telling my brother when things had first gone down: "I’m living with a stranger. I don’t know what’s happening."'
But despite a complicated history, Kendrick has remained friends with many of her exes, and currently, she appears to be single. As for whether she’ll ever want kids, she recently told The Guardian: 'I thought: "I’d have an easier time falling asleep with the weight of a cat on me. But I’m not responsible enough to own a cat. Someone should really make a robot cat that does all the purring and the kneading." And then I was like: wait, I’m not even up to the "cat lady: part! Why would anyone trust me with a kid?' Seems that settles that.
Ahead, take a deep dive into Anna Kendrick’s complete dating history.
Bill Hader (2020–2022)
Just like Kendrick, Hader likes to keep the details of his relationships private, and the news of their coupling arrived over a year after they’d been together—at least according to a report from People.
In January 2022, the outlet shared that: 'Anna has been dating Bill quietly for over a year. 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.' (The movie in question was the Disney holiday film Noelle, which came out in 2019.)
After playing brother and sister Noelle and Nick Kringle on screen, the two connected on a different level, and the COVID-19 pandemic apparently helped them to keep things under wraps. 'They are both very private people, and with the pandemic it was easy to keep it quiet,' the source added. 'They’re both hysterical so they must keep each other laughing all of the time.'
After years of going strong, it was reported in June 2022 that the two had called it quits.
Ben Richardson (2014–2019)
Kendrick first met Richardson on the set of Drinking Buddies, which they filmed together during the summer of 2012, but they aren’t believed to have started dating until 2014.
The following year, the pair were spotted together in New York City’s SoHo, where Kendrick appeared to be wearing an engagement ring.
As noted by the Daily Mail at the time, Kendrick had worn that same ring on a different finger during a Hawaiian vacation with Richardson the month prior. This either suggested that Richardson had proposed and they had to wait to get the ring resized, or Kendrick was just trying something out.
Seems the latter was the case, given that Kendrick shut down 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 jewellery!'
While it’s unclear when they stopped dating, Entertainment Tonight reported that Kendrick and Richardson were last spotted together in 2019.
Jake Gyllenhaal (2013)
While a relationship between Kendrick and Gyllenhaal was never confirmed, there were rumours of the pair’s relationship after they played an onscreen couple for the police thriller End of Watch (2012).
The two seemed to have an undeniable chemistry, as noted by Mario Lopez in an interview with Kendrick in September 2012. 'He’s a great kisser. He’s a real gentleman,' she said, when prompted about their on-screen smooches. She also added that Gyllenhaal was totally shaven for the role, but he’d grown a little bit more hair for his most recent project. 'I like a little scruffy Jake,' she added.
In 2014, Kendrick expressed her frustration when Gyllenhaal dropped out of the live-action remake of Into the Woods. 'I was so p*ssed at Jake, let me tell you,' Kendrick said in an interview with The Daily Beast. 'I texted him and said, "You’re abandoning me, and I’m never going to forgive you!" And then I saw the trailer to Nightcrawler and texted him again and said, "Wow, you inspire me every day."'
Edgar Wright (2009–2013)
Kendrick and Wright first met on the set of Scott Pilgrim vs. the World, in which Kendrick starred as the titular character’s sister, while Wright served as director and producer. Prior to working together, Kendrick was already a fan of the director, as she revealed in a Vanity Fair video interview in 2023.
'I’ll be honest, when I first read this script, I was like, "I don’t totally get this. But I love Shaun of the Dead, I love Hot Fuzz." And I just wanted to work with Edgar Wright,' she recounted. 'But I do remember [it] on paper being like, "I don’t know how this is gonna work, but I’m just gonna trust that he sees it"—which he did. It’s so awesome.'
Although it’s unclear when exactly their relationship started, Us Weekly reports that it was soon after meeting on set. The two Hollywood stalwarts stayed together for the next four years, splitting amicably in 2013.
Since then, things appear to remain genial between them, at least based on some of their public social media interactions. Kendrick also confirmed their continued friendship on an episode of Armchair Expert in 2023.
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