From her Oscar-nominated performance in Up in the Air to leading the blockbuster Pitch Perfect franchise and making her directorial debut with Woman of the Hour, Anna Kendrick has established herself as one of Hollywood’s most charismatic and versatile stars. Known for her sharp humor, relatable quick wit, and fierce commitment to personal privacy, she has kept much of her personal life out of the tabloid frenzy.
However, over her two decades in the spotlight, fans have always been curious about the men who have shared her journey behind the scenes. The Anna Kendrick relationships timeline features creative collaborations with visionary directors, award-winning cinematographers, beloved comedians, and fellow Hollywood A-listers.
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Anna Kendrick Relationships
Here is an up-to-date, chronological breakdown of Anna Kendrick’s romantic history and major relationships.
Anna Kendrick and Edgar Wright (2009–2013)
Anna Kendrick’s first major high-profile relationship began on the set of the cult-favorite action comedy Scott Pilgrim vs. the World in 2009, which was directed by acclaimed British filmmaker Edgar Wright.
- A Bicoastal Creative Spark: Despite their 11-year age difference, the pair hit it off while working on the film and began dating shortly after. For four years, they maintained a low-key romance while navigating the distance between Los Angeles and London. While Anna Kendrick rarely discussed their partnership publicly, she admitted that sudden paparazzi attention felt jarring during her rapid rise to stardom. The couple parted ways amicably in early 2013 due to conflicting schedules and long-distance pressures.
Jake Gyllenhaal (2011–2012)
While filming the intense cop drama End of Watch in 2011, Anna Kendrick and co-star Jake Gyllenhaal sparked widespread romance rumors.
- On-Screen Chemistry and Off-Screen Rumors: Playing a newlywed couple on screen, the actors developed an immediate, playful bond on set. Anna Kendrick later shared in interviews that the film’s intimate, guerrilla-style shooting methods caused them to stay in character continuously, sometimes holding hands even after the cameras stopped rolling. While their playful red-carpet chemistry and public praise for one another fueled tabloid speculation, both stars confirmed they were simply close friends and dedicated co-stars.
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Anna Kendrick and Ben Richardson (2014–2020)
In late 2014, Anna Kendrick began a steady, long-term relationship with British cinematographer Ben Richardson, whom she met while filming the indie comedy Drinking Buddies.
- A Quiet Six-Year Partnership: The pair kept their romance exceptionally private, rarely making formal red-carpet appearances together despite collaborating on additional film projects like Happy Christmas and Table 19. Over their six years together, they were occasionally spotted on low-key dates around Los Angeles and New York City. Though the couple quietly went their separate ways around 2020, their years together represented one of Anna Kendrick’s most grounded chapters.
Bill Hader (2020–2022)
Anna Kendrick found romance during the pandemic with Emmy-winning actor and comedian Bill Hader, whom she previously starred alongside in the 2019 Disney+ holiday movie Noelle.
- Connecting After Noelle: Although they first met years prior when Anna Kendrick hosted Saturday Night Live, the two connected romantically in late 2020. Their shared comedy background and mutual desire for privacy made them a natural match. Insiders revealed that quarantining together brought them close quickly, but after nearly two years of quiet dating, the couple amicably broke up in mid-2022.
Anna Kendrick and Alex Edelman (2025–Present)
Following a quiet period focused on her directorial work and personal growth, news broke that Anna Kendrick had found love again with Emmy and Tony Award-winning comedian and writer Alex Edelman.
- A Fresh Chapter in the Light: The couple was first publicly linked after celebrating Alex Edelman’s birthday together and being spotted on low-key date nights around California. Sources close to the actress noted that Anna Kendrick had met his family and that the relationship felt grounded, respectful, and meaningful. Both stars continue to balance their booming creative careers while prioritizing a healthy, supportive bond.
CelebLoves Commentary: Anna Kendrick’s journey through love and relationships reflects her trademark resilience and commitment to personal boundaries. Having navigated the pressures of fame while protecting her peace, her current chapter alongside Alex Edelman shows that finding the right balance of privacy, humor, and support is always worth the wait.
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