Anna Kendrick Relationship History: What Really Happened Behind the Scenes

Anna Kendrick is basically the queen of keeping us on our toes. One minute she’s the relatable, sharp-witted girl next door in Pitch Perfect, and the next, she’s dropping bombshells on a podcast that make you want to go back and re-read every tabloid headline from the last decade. Honestly, for years, the Anna Kendrick relationship history was one of the most low-key files in Hollywood. She wasn't out here doing red carpet debuts with every new flame or posting "soft launches" on Instagram.

She was quiet. Stealthy, even.

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But things changed recently. Between her vulnerable revelations about a "toxic" long-term ex and her new, surprisingly public romance with comedian Alex Edelman, the veil has finally lifted. If you’ve been trying to piece together who she actually dated and why she’s now strictly "therapy-first" when it comes to men, you’re in the right place.

The Early Years: Edgar Wright and the Scott Pilgrim Spark

It all started back in 2009. Anna was filming Scott Pilgrim vs. the World, and the director was the visionary British filmmaker Edgar Wright. They hit it off fast. This wasn't just a fleeting set crush; they stayed together for about four years.

They were the indie "it" couple that nobody actually saw.

Kendrick later admitted that the paparazzi attention during this time was terrifying for her. She told The Guardian that seeing photos of them together felt like "someone emailing a picture of you sleeping." It’s no wonder they kept things buried. They eventually split in early 2013, but surprisingly, they’ve stayed tight. You’ll still see them interacting on social media, and she’s mentioned in interviews that they remain close friends. It’s the kind of "good" breakup we all wish we could pull off.

The Long Road with Ben Richardson (and the Mystery "Toxic" Ex)

After Edgar, things got even more private. In 2014, Anna started dating cinematographer Ben Richardson. They met on the set of Drinking Buddies. If you haven't seen it, go watch—the chemistry in that movie is palpable, though Richardson was behind the camera.

This relationship lasted a staggering six years. Or maybe seven?

This is where the Anna Kendrick relationship history gets a little heavy. In late 2024 and early 2025, Anna went on the Call Her Daddy podcast and talked about a seven-year relationship that turned emotionally abusive. She didn't name the person. She never does. But the math has fans looking at the 2014–2020 window.

She described it as a "switch flipping."

One day everything was fine, and the next, she was living with someone who she didn't recognize. She even shared that they had created embryos together before the relationship imploded. That is heavy stuff for a woman who usually leads with a joke. It explains a lot about why she stayed out of the spotlight for a bit and why she’s so vocal now about the "sneaky" nature of emotional abuse.

The Bill Hader Chapter: Laughter in the Dark

When news broke in early 2022 that Anna Kendrick and Bill Hader were a thing, the internet collectively cheered. It felt right. Two of the funniest people in Hollywood? Yes, please.

They actually met years prior while filming the Disney+ Christmas movie Noelle, where they played siblings. Talk about a slow burn. They didn't start dating until well after the movie wrapped, likely sometime in 2020. Because of the pandemic, they were able to hide out and just... exist.

A source told People that they were "hysterical" together. They just made each other laugh. But by June 2022, it was over. No drama, no messy statements. Just two people who realize they might be better off as friends. It was short, sweet, and sadly, the end of our "comedy power couple" dreams.

Who Is Anna Kendrick Dating Now? Enter Alex Edelman

If you’ve been following the news in 2025 and early 2026, you know there’s a new name in the mix: Alex Edelman. He’s an Emmy-winning comedian (his special Just for Us is incredible) and, apparently, he’s the one who finally met Anna's strict "must be in therapy" criteria.

The two were first linked in early 2025 after being spotted grabbing coffee and driving around Los Angeles. This time, things feel different.

• She met his mom. (According to insiders, this happened around March 2025).
• They aren't hiding. They’ve been seen at low-key restaurants and even the Vanity Fair Oscar Party.
• The "Therapy Rule." Anna told InStyle she won't even kiss a man unless he’s been in therapy. Edelman, who often discusses his mental health and Jewish upbringing in his sets, clearly passed the test.

It’s refreshing to see her happy after the "toxic" years she described. Edelman seems to match her wit without the Hollywood ego, and frankly, we’re here for it.

The Reality of Dating in the Public Eye

Looking back at the Anna Kendrick relationship history, you see a pattern of a woman who values privacy over "clout." She doesn't use her partners for PR. In fact, she’s spent most of her career trying to protect them from the very fame that pays her bills.

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What have we learned from her journey?

First, longevity doesn't always equal health. Seven years is a long time to be with someone, but as Anna showed us, you can still lose yourself in that time. Second, the "funny girl" often has a lot of depth and pain behind the punchlines.

Actionable Insights for Fans and Daters

If you're looking at Anna's history and wondering what you can take away for your own life, here’s the breakdown:

1. The Therapy Non-Negotiable: Anna’s rule about dating men who have done the work is a game-changer. It ensures a baseline of emotional intelligence before you even get to the first date.
2. Privacy is a Choice: You don't have to post your partner to prove the relationship is real. In fact, the quietest relationships often have the strongest foundations.
3. Trust Your Gut on "The Switch": If someone's personality changes overnight, believe them. Don't spend years trying to find the "old" them.
4. Amicable is Possible: Just because a relationship ends doesn't mean it was a failure. Her continued friendship with Edgar Wright is proof that sometimes you just outgrow the "romance" part while keeping the "person" part.

Anna Kendrick is currently thriving, directing films like Woman of the Hour, and dating someone who seems to actually "get" her. Her history isn't just a list of names; it’s a roadmap of a woman learning her worth in a very loud industry.