Rachel Bilson Recalls Flirty Night With Justin Timberlake — and How It All Went Wrong

Justin Timberlake was once the object of Rachel Bilson‘s affection back in the early 2000s, but their flirtatious moment at a party took an unexpected turn, according to revelations made during Bilson’s podcast.

During Monday’s episode of her Broad Ideas podcast, the 42-year-old actress shared her encounter with the pop sensation at a party during their early years in Hollywood.

“In our day, Justin Timberlake was very big, right? Like, the biggest. Sorry, no disrespect — he’s still very big. We were all at a party, or something, and he was there, and I was so obsessed with him,” Bilson began, hesitating momentarily, before saying, “I can’t tell this story.”

However, her co-host, Olivia Allen, picked up where she left off, divulging how she inadvertently sabotaged the flirty encounter. “We were kicking it with him. We were making friends with him. [Rachel] went up to him, obviously, or he came to [Rachel],” Allen explained. “I got drunk and embarrassed myself a little because he was trying to flirt with Rachel. This is the truth. You want the truth. I was drunk and I [sat] in between them. … I was just drunk and wanted to keep talking to him.”

Bilson chimed in, emphasizing the awkwardness of Allen’s intervention, saying, “There was no room. Olivia planted herself [between us], squeezed herself [between us].”

Although Allen admitted to hindering the night with her tipsy actions, she said Timberlake took it all in jest. “He called me the enemy. The next time I saw him, he was like, ‘What’s up, enemy?'” Allen recounted.

Ultimately, it seems that fate had different plans for Bilson and Timberlake. Timberlake went on to marry actress Jessica Biel in 2012, and they have since welcomed two sons. Meanwhile, Bilson shares a daughter named Briar Rose, 8, with her ex-fiancé, Hayden Christensen, from whom she split in 2017.

In recent years, Bilson has been recognized for her candid discussions on topics like sex and relationships. However, her hesitancy to delve into the details of her encounter with Timberlake may stem from a recent professional setback. Earlier this year, she lost a job over comments she made about wanting to be “manhandled” by her sex partner.

“This is the first time it’s ever happened to me in my professional life that I lost a job this week because of things that were said,” Bilson revealed in a May episode of her podcast. “A job got taken away from me because I was speaking candidly and openly about sex in a humorous way on our friend’s podcast.”

Bilson explained that she wasn’t just in talks for the gig but had already been hired when it was abruptly pulled from her. She expressed her frustration, saying, “I’m a single mom — like, I need these jobs. Everything counts. I provide a lot for my family and my daughter. Regardless of anything else, it all matters. I’m frustrated, and it makes me want to shut up.”

Bilson is no stranger to divulging her bedroom preferences. In fact, during an August episode of her podcast, she shared that what she missed the most about her ex, Bill Hader, was “his big d**k.”

Bilson and Hader first sparked romance rumors with a coffee date in his hometown of Tulsa, Oklahoma, in December 2019. They made their red carpet debut at the 77th annual Golden Globes in January 2020, but they called it quits the following July. He’s most recently been linked to comedian and actress Ali Wong.

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