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Anna Kendrick, the star and director of Woman of the Hour, is known for keeping her dating life private. While she portrays dark and twisted relationships on screen, she rarely discusses her own romantic history publicly. Throughout the years, Kendrick has been linked to various Hollywood stars, including Bill Hader, Edgar Wright, Ben Richardson, and Jake Gyllenhaal, but she prefers to keep the details under wraps.

One of Kendrick’s notable relationships was with actor Bill Hader, which reportedly lasted from 2020 to 2022. The couple kept their romance low-key until news of their breakup surfaced in June 2022. Kendrick and Hader’s connection blossomed while filming the Disney holiday movie Noelle, where they played siblings on screen. Despite their split, sources revealed that the two remained close friends and shared a mutual sense of humor.

Another significant relationship in Kendrick’s dating history was with cinematographer Ben Richardson, whom she met on the set of Drinking Buddies in 2012. The couple was together from 2014 to 2019, and there were speculations about an engagement when Kendrick was spotted wearing a ring. However, Kendrick later clarified that it was just costume jewelry and not an engagement ring. The pair eventually went their separate ways in 2019.

While rumors circulated about a romance between Kendrick and Jake Gyllenhaal after starring together in the film End of Watch, the nature of their relationship was never confirmed. Kendrick praised Gyllenhaal’s kissing skills and gentlemanly demeanor during interviews, but their rumored romance remained unverified. Similarly, Kendrick’s relationship with director Edgar Wright, whom she worked with on Scott Pilgrim vs. the World, lasted from 2009 to 2013 before they amicably parted ways.

Despite her past relationships, Kendrick remains single and has expressed reluctance about having children in the future. She values her privacy and prefers to focus on her career rather than discussing her personal life in the media. Kendrick’s ability to maintain friendships with her exes showcases her maturity and grace in navigating past relationships.

While Kendrick’s dating history offers a glimpse into her personal life, the actress continues to captivate audiences with her talent and versatility on screen. As she explores complex relationships in her projects, Kendrick’s own romantic journey remains a mystery that she chooses to keep private.