Rachel Bilson recalls a flirty encounter with Justin Timberlake gone wrong

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Rachel Bilson has opened up about a flirty encounter with Justin Timberlake that was ruined by her podcast co-host, Olivia Allen.

In a recent episode of their Broad Ideas podcast, the Hart of Dixie actor revealed that she once harboured a crush on the former NSYNC member. They even shared a flirtatious moment at a Hollywood party in the early 2000s, according to Bilson.

“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, before she decided to backtrack. “I can’t tell this story.”

Allen took over for Bilson, revealing that it was her fault the encounter didn’t go any further than light, flirty banter. “We were kicking it with him. We were making friends with him. [Bilson] went up to him, obviously, or he came to [Bilson],” 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 added that Allen “squeezed herself” between them and inadvertently made the situation awkward, saying: “There was no room. Olivia planted herself [between us].”

Despite Allen’s tipsy actions, Timberlake took it in stride. “He called me the enemy. The next time I saw him, he was like, ‘What’s up, enemy?’” Allen recalled, admitting that she probably prevented anything more from happening that night.

Timberlake ultimately married actor Jessica Biel in 2012. The longtime couple shares two sons: Silas, eight and Phineas, two. Meanwhile, Bilson welcomed daughter Briar Rose, eight, with ex-fiancé Hayden Christensen in 2014.

Bilson and Christensen split in 2017 after nearly 10 years together. In 2007, sparks flew when the pair first met on the set of the sci-fi film Jumper, in which they played each other’s love interest. At the time, they were both 26 and Bilson had recently ended her three-year relationship with her OC co-star, Adam Brody.

They were engaged the following year, but called off their engagement for three months in 2010 before ultimately getting back together.

Speaking to People in 2014, Christensen explained that they named their daughter Briar Rose after the Disney princess in the 1959 version of Sleeping Beauty. “There’s a Disney reference there, I suppose. The original Sleeping Beauty is called Briar Rose. Rachel - we both love Disney - but Rachel, especially, was very keen on the name.”

According to People, personality differences ultimately led to the former couple calling off their engagement in 2017.

“Rachel is very outgoing, and her friends are very important to her. Hayden is the opposite. He can be very antisocial,” a source claimed, adding: “Hayden never wanted to join her for special occasions, like weddings. Rachel had to attend by herself.”

Since their split, the former couple have remained committed to co-parenting Briar Rose, with both of them being open about how they try to maintain a healthy dynamic for their daughter.

“Communication is key and just being on the same page, so everything’s about the kid,” she told People in 2021. “As long as you put the kid first, everything will be okay.”