Rachel Bilson Recalls Flirting With Justin Timberlake at a Party

Justin Timberlake was tearin’ up Rachel Bilson’s heart in the early 2000s. 

The O.C. alum, 42, revealed during the Monday, September 25, episode of her “Broad Ideas With Rachel Bilson” podcast that she and Timberlake, 42, once sparked a flirtation at a party before cohost Olivia Allen ruined their moment. 

“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,” she began, before stopping short to say, “I can’t tell this story.” 

Allen, however, continued for her, recalling how she blew her friend’s big moment. 

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“We were kicking it with him. We were making friends with him. [Rachel] went up to him, obviously, or he came to [Rachel],” she said. “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.” 

While Bilson was hesitant to expand on the story herself, she emphasized how awkward Allen’s move was. “There was no room. Olivia planted herself [between us], squeezed herself [between us],” she quipped.  

Allen admitted she soured the night with her tipsy actions — Bilson said her pal “battled” Timberlake all night long — but noted that the ‘NSync singer was “great” and took it all in jest. “He called me the enemy. The next time I saw him he was like, ‘What’s up, enemy?’” 

“He wasn’t mad at me. You might have been,” she joked to Bilson. 

The twosome were seemingly never meant to be. Timberlake married Jessica Biel in 2012 and the pair welcomed sons Silas and Phineas in 2015 and 2020, respectively. Bilson, meanwhile, shares daughter Briar Rose, 8, with ex-fiancé Hayden Christensen. The twosome were together for nearly a decade before calling it quits in 2017.

In recent years, Bilson has become known for speaking candidly on topics like sex and relationships. Her hesitancy to take a walk down Timberlake lane, however, may stem from losing a job earlier this year 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 during a May episode of her “Broad Ideas” 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. The gig was then pulled from her “because I was speaking openly about sex.” She noted that she was “baffled” by the decision to fire her over “being candid and honest and the subject was sex” in “this day and age” — and the incident now has her reconsidering what she says. 

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“I didn’t even have a chance to defend myself,” Bilson continued. “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 declared. “I feel shamed by this company.”