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Who is Olivia Allen? Rachel Bilson claims she could've hooked up with Justin Timberlake if it wasn't for drunk friend

Rachel Bilson recently opened up about being hit on by Justin Timberlake at an early 2000s party and recalled how Olivia Allen embarrassed them
UPDATED SEP 27, 2023
Rachel Bilson and her best friend Olivia Allen recently shared about their encounter with Justin Timberlake (Getty Images, @obliviaallen/Instagram)
Rachel Bilson and her best friend Olivia Allen recently shared about their encounter with Justin Timberlake (Getty Images, @obliviaallen/Instagram)

LOS ANGELES, CALIFORNIA: In a recent episode of her podcast 'Broad Ideas', Rachel Bilson unveiled a surprising and nostalgic chapter from her past, revealing the intriguing story of how her longtime best friend and podcast co-host Olivia Allen inadvertently disrupted what could have been a romantic encounter with pop sensation Justin Timberlake.

As per Bilson, the story unfolds in the early 2000s when she and Timberlake were both fixtures in the entertainment industry, and one day, the 'Jumper' actress found herself at a party where fate brought her into the 'Mirrors' singer's orbit.

While recalling the incident, she admitted, "I was so obsessed with him."

NEW YORK, NEW YORK - FEBRUARY 06: Rachel Bilson attends the Christian Siriano Fall Winter 2020 NYFW
Rachel Bilson was once obsessed with Justin Timberlake (Getty Images)

Rachel Bilson almost ended up with Justin Timberlake

However, it wasn't Rachel Bilson who narrated the entire incident as her friend, Olivia Allen, stepped in to shed light on the unforgettable night.

She described how they were mingling with Timberlake, who was at the time famous for hits with NSYNC.

Justin Timberlake attends the Los Angeles Premiere FYC Event for Hulu's
Justin Timberlake was a part of the popular boy band NSYNC (Getty Images)

"We were kicking it with him," recalled Allen, adding, "We were making friends with him."

But the plot took an unexpected twist when Timberlake began showing interest in Bilson. "[Rachel] went up to him, obviously, or he came to [Rachel]," explained Allen, continuing, "I got drunk and embarrassed myself a little because he was trying to flirt with Rachel."


 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by Olivia Allen (@obliviaallen)


 

Justin Timberlake termed Olivia Allen the 'enemy' 

"I was drunk and I [sat] in between them," admitted Olivia Allen, adding, "I was just drunk and wanted to keep talking to him."

Rachel Bilson chimed in, confirming the awkwardness of the moment. "There was no room," said the actress, continuing, "Olivia planted herself [in the middle and] squeezed herself [in between us]."


 
 
 
 
 
View this post on Instagram
 
 
 
 
 
 
 
 
 
 
 

A post shared by @rachelbilson


 

Despite the unexpected interruption, Justin Timberlake managed to take it all in stride. "He called me the enemy," said Allen as she laughed, and added, "The next time I saw him, he was like, 'What's up, enemy?'"

LOS ANGELES, CALIFORNIA - MAY 09: (L-R) Jessica Biel and Justin Timberlake attend the Los Angeles Pr
Jessica Biel and Justin Timberlake tied the knot in 2012 (Getty Images)

Even though Bilson and Timberlake's romantic journey failed to take off, he crossed paths with actress Jessica Biel in 2007.

Although the pair briefly separated in 2011, they rekindled their romance and married in 2012. Today, the couple is the proud parents of two sons, Silas and Phineas, showcasing a love that has stood the test of time. 

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