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Jason Sudeikis was already in a relationship by the time GLOW star Alison Brie was convinced to make a move on the actor. And given the timeframe, it’s possible the person he was going out with was Olivia Wilde.

Alison Brie was almost set up on a date with Jason sudeikis

Alison Brie posing in a dress at the Los Angeles premiere of the Los Angeles Premiere of Prime Video's "Somebody I Used To Know".
Alison Brie | Axelle/Bauer-Griffin/FilmMagic

Brie had a momentary interest in the Ted Lasso star several years ago. Dan Harmon, who was the showrunner for Brie’s hit comedy Community, tried to play matchmaker with the pair. But by the time Harmon convinced Brie to pursue Sudeikis, it turned out Sudeikis was already taken.

“We never dated but prior to this movie, about four or five years ago, Dan… texted me one day and was just like, ‘Would you mind if I set you up with Jason Sudeikis?’ And I was like, ‘No, that sounds great!’ And then 20 minutes later he’s like, ‘Oh, never mind, he’s seeing someone,’” Brie once said in a 2015 interview with The View (via Daily Mail).

The person who Sudeikis might’ve been seeing at the time was Olivia Wilde. Sudeikis was dating the actor in 2011, which seems to fit the timeframe Brie was referring to. But Sudeikis could’ve also been in a relationship with January Jones when Harmon texted the star. The pair dated in 2010 after Jones hosted an episode of Saturday Night Live. But their relationship was short-lived.

Alison Brie and Jason Sudeikis starred in ‘Sleeping With Other People’

Ironically, Brie and Sudeikis would star in Sleeping With Other People after almost dating. The film was about two friends who had a one-night stand, then eventually reconnected by chance years later. But the film also marked a memorable moment in Brie’s career. It was the first time the Community star had to engage in a love scene, which was an interesting experience for the actor.

“I hadn’t really done sex scenes before, so that was a new thing for me,” Brie once told Cosmopolitan.

Brie credited the movie’s director and screenwriter, Leslye Headland, for how well the love scenes were done. Headland chose not to include nudity in Brie’s sequence, which Brie felt enhanced the take.

“Leslye is brilliant at writing in general and at writing sex scenes that are so complex, that are highly emotional. You’re taking this journey with the characters and yet there’s no nudity, they’re still so erotic and sexy, and I think that feels realistic too in a way. There’s an urgency to these sex scenes that makes them sexy,” she said.

Brie considered herself fortunate that she managed to do her first love scene in Headland’s careful hands.

“And it was really nice to do that, considering it was my first time, with this director who is so sensitive to female exploitation and things like that, and wanting to avoid that. So it was good, it was a safe place,” she said.

Alison Brie was the type of celebrity Jason Sudeikis would’ve wanted to date as a teenager

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Sudeikis couldn’t have enough nice words to say about his Sleeping co-star. The Emmy winner confided that when Brie was recruited for the project, he looked forward to his time on the film even more.

“When Alison came on, that was super exciting, because I’ve been a fan of her for a long time,” he once told Vanity Fair. “She has that same quality of those women that I fell in love with as a teenager, watching that golden era of rom-coms, whether it just be, just to name one, Meg Ryan. That same sort of girl next door that you had a shot with if you were the best version of yourself.”