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Anna Kendrick might be best known for her sharp wit, musical chops, and unforgettable roles in films like Pitch Perfect and Up in the Air, but when it comes to her real-life love stories, she tends to keep things very close to the chest.
The Another Simple Favour star has explored some truly wild romantic tales onscreen, yet she rarely shares much about her personal relationships. Still, over the years, a few romances have quietly come to light, ranging from high-profile comedians to acclaimed filmmakers.
So, who has Anna Kendrick dated? From long-term relationships to rumoured flings, here’s everything we know about her dating history.
Who was Anna Kendrick’s first known Hollywood boyfriend?
Edgar Wright (2009–2013)
Anna Kendrick met British director Edgar Wright on the set of Scott Pilgrim vs. the World in 2009. Wright directed the cult classic while Kendrick played Scott’s younger sister, Stacey Pilgrim. The two quietly dated for about four years, keeping their relationship largely out of the spotlight.
In a 2012 interview with The Guardian, Kendrick admitted how unsettling it was to be photographed with Wright: “It was like someone emailing a picture of you sleeping… It felt scary and dangerous. It still does.” Though the pair split in 2013, they’ve remained on friendly terms, even joking on social media years later about casting Kendrick as Marvel’s Squirrel Girl.
Did Anna Kendrick date Jake Gyllenhaal?
Jake Gyllenhaal (Rumored, 2013)
While never confirmed, rumours swirled that Kendrick had a brief fling with Jake Gyllenhaal after the two co-starred in End of Watch (2012). Their chemistry both onscreen and off had fans buzzing, especially after Kendrick gushed about Gyllenhaal being “a great kisser” in an interview.
She also revealed in 2014 that she was “pissed” when he dropped out of Into the Woods, but later called him “inspiring.” Romantic or not, the mutual admiration was very real.
How long did Anna Kendrick date Ben Richardson?
Ben Richardson (2014–2019)
Kendrick’s longest confirmed relationship was with British cinematographer Ben Richardson. The two met while filming Drinking Buddies and began dating in 2014. They were spotted together several times over the years, including during a New York stroll in 2015 when Kendrick was seen wearing what looked like an engagement ring.
However, she quickly shut down engagement rumours, calling the accessory “costume jewellery” in an interview with Marie Claire. The couple kept things extremely low-key and were last seen together in 2019 before quietly splitting.
Was Anna Kendrick engaged to Bill Hader?
Bill Hader (2020–2022)
In one of her most surprising (and secretive) romances, Kendrick reportedly dated Barry actor Bill Hader from 2020 to 2022. The two had previously worked together on Noelle (2019), playing onscreen siblings.
According to People, they had been dating quietly for over a year before the news went public in 2022. A source shared: “They’re both very private people… and with the pandemic, it was easy to keep it quiet.” Sadly, they broke up later that year.
Did Anna Kendrick talk about an abusive relationship?
Yes, though she hasn’t named names
In various interviews, Kendrick has opened up about surviving a deeply damaging long-term relationship. During a 2023 episode of the Armchair Expert podcast, she revealed she had lived with a partner who changed “in an instant,” leaving her feeling like she was “living with a stranger.”
She elaborated further on Call Her Daddy in 2024, describing how she blamed herself for the emotional abuse she endured over seven years. “I turned my life completely upside down trying to fix whatever was wrong with me,” she said.
While Kendrick hasn’t confirmed which ex she was referring to, her honesty has been praised for shedding light on the complexities of toxic relationships.
Is Anna Kendrick dating anyone now?
As of 2025, Anna Kendrick appears to be single. She hasn’t been publicly linked to anyone since her split from Bill Hader and continues to focus on her career.
As for motherhood? She recently told The Guardian that she’s not even ready for a cat, joking, “Why would anyone trust me with a kid?
