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

'The O.C.' actress admitted she was "so obsessed" with the singer-songwriter in the early 2000s on Monday's episode of her 'Broad Ideas' podcast

Rachel Bilson is looking back at a missed opportunity with Justin Timberlake.

On Monday's episode of her Broad Ideas podcast, The O.C. actress, 42, shared a story about an "embarrassing" drunken encounter she had with the singer-songwriter, 42, at a party back in the early 2000s.

"In our day, Justin Timberlake was very big, right? Like, the biggest. Sorry, no disrespect — he’s still very big," she started, speaking to 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 that she couldn't tell the story. But her co-host wasn't about to let her off the hook so easily.

Related: Rachel Bilson's Dating History: From Adam Brody to Bill Hader

"We were kicking it with him. We were making friends with him. [Bilson] went up to him, obviously, or he came to [Bilson]," Allen chimed in. "I got drunk and embarrassed myself a little because he was trying to flirt with Rachel."

She then planted herself in 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."

The Hart of Dixie star recalled how awkward things got then, emphasizing how her pal just "squeezed herself" right in. Luckily, Timberlake seemed to be a good sport about it — though he didn't pass up his chance to tease Allen a little.

"The next time I saw him, he was like, 'What’s up, enemy?'" she recalled.

Alas, things just weren't meant to be. Timberlake married actress Jessica Biel in Oct. 2012, tying the knot in a ceremony in Italy. They share two kids, 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, Jumper. She also previously dated Bill Hader and her O.C. costar Adam Brody.

The actress has never been one to hold back when it comes to discussing sex and her dating life.

In May, she claimed she lost an acting job for "speaking candidly and openly about sex in a humorous way," referring to when she detailed her bedroom preferences on an episode of the Women on Top podcast.

Related: Rachel Bilson Tells Whitney Cummings She Hadn't Experienced an Orgasm from Sex Until She Was 38: 'Crazy'

At the time, Bilson joked that she wanted to be "f---ing manhandled" and shared that she preferred the missionary position. She later admitted she was "baffled" by the criticism.

"First of all, I said it in a joking manner in the interview, like, 'Yeah, I wanna get f---ing get manhandled,'" she explained on Broad Ideas. "Basically, it's like, 'Okay, give control or take control in the bedroom,' whatever."

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"A single mom, a woman, lost a job because they were being candid and honest and the subject was sex," the actress added. "I didn't even have a chance to defend myself."

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