Rachel Bilson Shares the ‘Embarrassing’ Drunken Encounter She Once Had with a Flirty Justin Timberlake

Rachel Bilson reflects on her missed opportunity with Justin Timberlake.

In her episode on Monday Broad ideas podcast, OC the actress (42) shared the story of an “embarrassing” drunken encounter she had with the singer-songwriter (42) at a party in the early 2000s.

“In our time, Justin Timberlake was very big, wasn’t he? Like, the biggest. Sorry, no offense – he more really big,” she began, addressing her co-host Olivia Allen. “We were all at a party or something, and he was there, and I was so obsessed with him.”

Bilson then hesitated, claiming she couldn’t tell the story. But her co-host wasn’t about to let her off the hook so easily.

Rachel Bilson at the 2023 SCAD TVfest at the Four Seasons Atlanta on February 9, 2023 in Atlanta, Georgia.

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“We were angry with him. We became friends with him. [Bilson] went to him, apparently, or came to himself [Bilson]” Allen chimed in. “I got drunk and embarrassed myself a bit because he was trying to flirt with Rachel.”

She then placed herself between Bilson and Timberlake. She admitted that she kind of sabotaged her friend’s potential moment with the *NSYNC singer, explaining, “I was just drunk and wanted to keep talking to him.”

Justin Timberlake at the Los Angeles Premiere of FYC Event for Hulu’s “Candy” at the El Capitan Theater on May 9, 2022 in Los Angeles, California.

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The Hart of Dixie The star recalled how things got awkward then, stressing how her friend simply “squeezed in”. Thankfully, Timberlake seemed to be a good sport about it — though he didn’t miss an opportunity to tease Allen a little.

“The next time I saw him, he said, ‘What’s up, enemy?'” she recalled.

Alas, things just weren’t meant to be. Timberlake married actress Jessica Biel in October 2012, tying the knot in a ceremony in Italy. They have two children, sons Silas, 8, and Phineas, 2.

Meanwhile, Bilson shares daughter Briar Rose, 8, with her ex Hayden Christensen, whom she met on the set of the 2008 film. Sweater. She also previously dated Bill Hader and her OC actor Adam Brody.

Hayden Christensen and Rachel Bilson at a cocktail party honoring designer Kris Van Assche in 2009.

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The actress has never held back when it comes to discussing sex and her love life.

In May, she said she lost her acting job because she was “honest and open about sex in a humorous way,” referring to when she detailed her bedroom preferences in the episode Women on top podcast.

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At the time, Bilson joked that she wanted to be “fucking bullied” and said she preferred the missionary position. She later admitted she was “confused” by the criticism.

“First of all, I said it jokingly in an interview, like, ‘Yeah, I want to be fucking bullied,'” she explained on Broad ideas. “Basically, it’s like, ‘Okay, give control or take control in the bedroom,’ whatever.”

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“One mother, a woman, lost her job because they were honest and forthright and the subject was sex,” the actress added. – I didn’t even have a chance to defend myself.

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Source: HIS Education