Anna Kendrick’s Dating History: Bill Hader, Ben Richardson and More

A low-key kind of love. Anna Kendrick has remained relatively private when it comes to her dating history — but she's been linked to some A-list stars. The Twilight actress' personal life began to make headlines in 2009 when she sparked a romance with Scott Pilgrim vs. The World director Edgar Wright. After four years of dating, Us Weekly confirmed that the duo went their separate ways. As her star continued to rise in Hollywood, the Up in the Air actress attempted to keep her relationships under wraps. By January 2022, Kendrick's love life became a hot topic once again when she was linked to Bill Hader. "They were both single at the same time," a source exclusively told Us of how the romance began. "They're really into each other and make each other laugh — a lot. They're keeping their relationship private, but friends close to them know." At the time, the insider revealed that the Pitch Perfect star had "already bonded" with Hader's children — Hannah, Harper and Hayley — whom he shares with ex-wife Maggie Carey. (The former spouses were married from 2006 to 2018.) Before calling it quits in mid-2022, Hader and Kendrick rarely commented on their romance. The Saturday Night Live alum explained in March 2022 that he wanted to keep quiet for the sake of his kids. "They just want me to be their dad," the Skeleton Twins star told The Hollywood Reporter. "They just want me to sit and watch Encanto over and over and over again. So that's what I do." The Last Five Years actress, meanwhile, gradually began to open up about some of her more challenging dating experiences — without naming names. During an eye-opening appearance on the "Armchair Expert" podcast, Kendrick detailed the turning point of a relationship with a toxic ex. "I was with someone — this was somebody I lived with, for all intents and purposes my husband. We had embryos together, this was my person," she said in January 2023, adding that she realized something didn't feel right "six years" into the romance. "I remember telling my brother, when things had first kind of gone down, 'I'm living with a stranger. Like, I don't know what's happening.'" Kendrick recalled trying to work things out in couples therapy before revealing that her former partner eventually confessed his feelings for someone else. "I did start going to Al-Anon while all this was going on," she admitted. "I mean, look, I truly dismantled my life. ... I started seeing two therapists a week and I started trying to learn to meditate and I got into Al-Anon. And all of these things ended up being very wonderful things for me in the long run, but initially went into them thinking, 'Tell me how to stop being crazy. Tell me how to stop feeling anything.'" Scroll down for a look at Kendrick's relationship history: