Anna Kendrick’s Dating History: A Look at the Actress’ Relationships in Hollywood — and What She’s Said About Past Boyfriends

Anna Kendrick often explores about love on the big screen, but in real life, she keeps mum about her relationships.

The Woman of the Hour actress dated director Edgar Wright from 2009 to 2013, cinematographer Ben Richardson from 2014 to 2020 and Barry star Bill Hader from 2020 to 2022, but she doesn’t publicly name her exes.

Kendrick did, however, open up in May 2020 about generalities in her past relationships. While discussing her HBO Max series Love Life, she explained to The Sydney Morning Herald that the show’s arc aimed to portray “how we learn from each relationship.”

“Looking back now, it’s like, ‘Oh god, I acted like such a jerk in that relationship.’ Or all the times I didn’t feel strong enough to say, ‘You can’t speak to me that way,’ ” she said. “I’m just so happy that I’m clearer now about what I will accept from people in my life.”

Kendrick has also found healing through her work. She filmed 2022’s Alice, Darling not long after a negative personal experience. Speaking to PEOPLE in September 2022, the actress said the script “resonated” with her and it “felt incredibly cathartic” making the movie.

Here’s a look back at Anna Kendrick’s dating history.

Edgar Wright

Anna Kendrick met English filmmaker Edgar Wright in 2009 when the two filmed 2010’s Scott Pilgrim vs. the World. Kendrick starred in the cult classic as Stacey Pilgrim, the sister to Michael Cera’s Scott Pilgrim, while Wright directed the movie.

“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,” the Pitch Perfect star recalled to Vanity Fair in February 2023. “But I do remember this 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.”

Kendrick and Wright dated for four years and kept their relationship private. In May 2012, she told The Guardian how emotional it was to see paparazzi photos of her and Wright.

“I started crying immediately. It was like someone emailing a picture of you sleeping,” she told the outlet. “It felt scary and dangerous. It still does.”

Kendrick and Wright broke up in 2013 and have stayed friendly. Three years later, Wright campaigned on X (formerly Twitter) for Kendrick to be cast as Squirrel Girl in a since-deleted tweet. They then jokingly went back and forth on who she’d fight in a possible live-action version of the Marvel comic, though one hasn’t been greenlit.

The former couple also worked together again on Netflix’s 2023 animated series Scott Pilgrim Takes Off, in which Kendrick lent her voice and reprised her role as Stacey while Wright was an executive producer.

Ben Richardson

Kendrick appears to have been introduced to cinematographer Ben Richardson when they collaborated on the 2013 dramedy Drinking Buddies.

As the A Simple Favor star rarely speaks publicly about her relationships, her and Richardson’s exact timeline is unknown, but they reportedly dated from 2014 to 2020. The two were last photographed together in 2019, according to Entertainment Tonight.

In a May 2020 interview with Kendrick, The Sydney Morning Herald noted that the actress wouldn’t confirm her then-partner’s name but did share the difficulties of staying tight-lipped about her love life.

“Well, as far as keeping it private, it isn’t easy, as you are proving right now,” she told the outlet. “But that’s just always how it’s been for me.”

Bill Hader

Kendrick met Bill Hader years before they began dating in 2020.

The actors were connected professionally. Apart from sharing a connection to Saturday Night Live — Hader starred on the NBC late-night show until 2013, and Kendrick hosted the following year — they worked together on Disney+’s 2019 holiday film Noelle, in which they played siblings.

In January 2022, a source told PEOPLE that the pair got together “well after the movie.”

“Anna has been dating Bill quietly for over a year,” they added. “They are both very private people, and with the pandemic, it was easy to keep it quiet. They’re both hysterical so they must keep each other laughing all of the time. She’s really, really happy.”

The following month, another source told PEOPLE that Kendrick and Hader made a “great couple.”

“You can see the chemistry when they’re together,” the source said. “They have a really fun rapport, very sarcastic and funny but all coming from a place of love. … 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.”

Kendrick and Hader broke up in June 2022 after two years of dating, Entertainment Tonight first reported. Reps for both actors declined to comment for PEOPLE at the time.

Hader had previously dated Rachel Bilson for six months in 2020 and been married to Maggie Carey, with whom he shares three daughters, from 2006 to 2018. The actor is currently in a relationship with comedian Ali Wong.