During a podcast, one or two celebrities get into a relaxed chat and talk a little bit about what’s going on. This also applies to actress Rachel Bilson, who suddenly unpacks a funny, unsuccessful dating story with her long-time friend Olivia Allen. The main actors, the two ladies themselves and none other than the singer Justin Timberlake.

In the late ’90s and early 2000s, Rachel Bilson was among the countless, mostly female fans who idolized NSYNC. The 42-year-old confessed and told a little anecdote from a Hollywood party from the time when Timberlake was at the height of his career.

On her podcast “Broad Ideas with Rachel Bilson” on September 25, 2023, she revealed: “At the time, Justin was very tall, wasn’t he? The tallest, so to speak. Sorry, no disrespect – he’s still very tall.” She elaborates: “We were all at a party, he was there and I was so obsessed with him.” Olivia Allen added that Bilson and Timberlake chatted happily at the party.

Allen goes into more detail, saying she doesn’t know exactly whether Bilson was approaching Timberlake or vice versa, but she does remember an embarrassing situation in which she apparently kept disturbing them: “I got drunk and embarrassed myself a little “Because he tried to flirt with Rachel.” And then it got even worse. Although Timberlake apparently tried to flirt with Bilson, her best friend Olivia Allen simply sat between them. Allen blames the alcohol: “I was just drunk and wanted to keep talking to him.”

Bilson then interrupts and confirms that Allen made the moment very uncomfortable. “There was no room!” she says and explains to the listeners: “Olivia squeezed herself in the middle between us!” Luckily, Timberlake could only laugh about it. Allen continues: “He called me the enemy,” she recalls. “The next time I saw him he asked, ‘How’s it going, enemy?'”

In 2007, Rachel Bilson’s chance to get close to Justin Timberlake was over. The singer met Jessica Biel, fell in love, married her in 2012 and had two children with her.

Sources: Podcast, E Online, Daily Mail

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