Everything We Know About Anna Kendrick's Past Relationships

Anna Kendrick has become a household name over the years. The actor first grabbed attention in a supporting role in the wildly popular "Twilight" series. She later went on to star in "Up in the Air" with George Clooney, for which she earned an Oscar nomination, and then dazzled fans with her singing voice and comedy chops in the "Pitch Perfect" movies. However, she was working in the entertainment business long before that. Kendrick debuted on Broadway when she was just 12 years old. She even earned a Tony nomination for her role in "High Society."

Over the years, Kendrick has appeared in other projects such as "Scott Pilgrim vs. the World," "The Last Five Years," "Into the Woods," "A Simple Favor," and "Alice, Darling." She's also lent her voice to the role of Poppy in the popular kids' movie franchise "Trolls" alongside Justin Timberlake.

Of course, with Kendrick's career success and fame, her love life has become the topic of conversation among fans and entertainment news sources. Although the actor has kept her romances relatively private, she has dated some well-known men in Hollywood over the years.

In 2009, Anna Kendrick met British filmmaker Edgar Wright on the set of the film "Scott Pilgrim vs. the World." The couple hit it off and began dating while the film was still in production. However, the duo didn't flaunt their romance. Instead, they kept their relationship extremely private for many years and rarely publicly commented on their five-year relationship. They split in March 2013 when sources told Us Weekly that the couple had called it quits and that the "Twilight" star was single.

The pair never revealed the reason behind their split. However, Kendrick did reveal that the media and paparazzi were a source of stress for her in the relationship, admitting that she hated when she stumbled upon paparazzi photos of the duo together. "I started crying immediately," she told The Guardian in 2012. "It was like someone emailing a picture of you sleeping. It felt scary and dangerous. It still does. I try to ignore it."

Despite their breakup, Kendrick and Wright apparently parted on good terms. During a 2023 interview with Dax Shepard's "Armchair Expert," the actor confirmed that she and the director are still very close (via Page Six). They've even interacted with each other on Twitter since their split.

Following Kendrick's split with Edgar Wright, she began dating British cinematographer and director Ben Richardson. The two met on the set of the film "Drinking Buddies" and kicked off a nearly six-year romance. Richardson has an impressive career resume, working on movies such as "The Fault In Our Stars" and "Beasts Of The Southern Wild." He's also credited for working on popular TV shows such as "Yellowstone" and "Mare Of Easttown." He, like Kendrick, has also received critical acclaim for his work, being nominated for four Oscars and winning awards at the Sundance Film Festival and the Film Independent Spirit Awards.

After beginning a relationship, the pair also worked on the movies "Table 19" and "Happy Christmas." During their time together, Kendrick and Richardson kept their romance completely private. However, during their relationship, the actor was spotted wearing a diamond ring on her left hand. Of course, she never publicly commented on the rumors that the couple were engaged.

Kendrick and Richardson split in 2020. That same year, the actor opened up about past relationships, telling the Sydney Morning Herald, "Even though our relationships end, it doesn't mean they are complete failures. People come into your life and you grow and they change you, and what you learn from them might be really positive or it might be negative."

In January 2022, news broke that Anna Kendrick had been dating comedian Bill Hader for over a year. Hader, who is known for his time on "Saturday Night Live," movies such as "IT" and "Trainwreck," as well as his HBO series "Barry," also starred in the film "Noelle" with Kendrick in 2019. "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," a source told People Magazine of the then-couple.

The duo reportedly began dating in 2021 and kept their romance under wraps for quite some time. "They are both very private people, and with the pandemic it was easy to keep it quiet," the source revealed. "They're both hysterical, so they must keep each other laughing all of the time. She's really, really happy." Us Weekly sources also confirmed the relationship, adding that Kendrick had gotten close to Hader's daughters Hannah, Harper, and Hayley, whom he shares with his ex-wife Maggie Carey.

Sadly, Kendrick and Hader's quiet relationship didn't last, and the pair had reportedly called it quits by June 2022.

Although Anna Kendrick was reportedly in some long-term relationships during the earlier days of her Hollywood career, the actor couldn't stop the rumor mill from speculating about a possible romance with one of her A-list co-stars. Kendrick filmed the movie "End of Watch" with Jake Gyllenhaal, which led to the pair being spotted looking very cozy with one another in 2011. Although nothing was ever confirmed, there were rumors that sparks were flying between the duo and that a possible romance was brewing.

For her part, Kendrick added fuel to the fire when she spoke out about how intimate she felt with Gyllenhaal on set. "We were shooting [End of Watch] on tiny cameras with very little lighting and a very small crew. There was a lot of improv. It felt incredibly intimate. You're in character all the time because you're shooting all the time. So, Jake and I would be holding hands and suddenly we'd be like, 'Oh, we're not filming,'" she told E! News at the time.

Of course, due to Kendrick and Gyllenhaal's private nature regarding their relationships, any possible romance was never made public.

In 2022, Anna Kendrick promoted her film "Alice, Darling," a tale of one woman's struggle to deal with an abusive partner. The actor revealed that the movie felt a bit personal to her as she could relate to what the character was going through because she had also been in a toxic and emotionally abusive relationship in the past.

"I was coming out of a personal experience with emotional abuse and psychological abuse. I was in a situation where I loved and trusted this person more than I trusted myself. So when that person is telling you that you have a distorted sense of reality and that you are impossible and that all the stuff that you think is going on is not going on, your life gets really confusing really quickly," Kendrick told People Magazine. Of course, Kendrick refused to name the ex-boyfriend that she had been speaking about. However, she did admit that dealing with that relationship was one of the hardest things she's ever had to deal with.

Although Kendrick has seemingly yet to find her perfect match, fans are rooting for the beloved actor to eventually get her happy ending.