Rachel Bilson Says She LOST a Job Over Sex Comments

Rachel Bilson's chances with Justin Timberlake went bye bye bye after an awkward encounter in the early aughts.

The O.C. alum recently revealed that she and the pop star once crossed paths at a Hollywood party at the height of *NSYNC's fame, though her "embarrassing" attempts to flirt with him were thwarted by her friend and Broad Ideas co-host Olivia Allen.

"In our day, [Justin] was very big, right? Like, the biggest. Sorry, no disrespect—he's still very big," Rachel, now 48, began on the Sept. 25 episode of the podcast. "We were all at a party, or something, and he was there, and I was so obsessed with him."

And while Rachel and Justin, now 42, were "kicking it" at first, according to Olivia, the pair quickly learned that three's a crowd.

"I got drunk and embarrassed myself a little because he was trying to flirt with Rachel," Olivia shared, explaining that she "wanted to keep talking" to Justin and kept crashing his conversation with the Hart of Dixie star.

photos35 Reasons to Love Justin Timberlake

"There was no room," Rachel recalled, adding that eventually Olivia "squeezed herself" in between them and "battled" the singer throughout the night. 

Paras Griffin/Getty Images; Momodu Mansaray/Getty Images

As for Justin's reaction? According to Olivia, he took it in stride and even poked fun at the situation when they later reconnected.

"The next time I saw him he was like, ‘What's up, enemy?'" she said. "He wasn't mad at me."

In the end, Justin found himself lovestoned with Jessica Biel, who he married in 2012. The couple share sons Silas, 8, and Phineas, 2.

Meanwhile, Rachel is mom to daughter Briar Rose, 8, with ex Hayden Christensen, who she split with in 2017 after 10 years together.

Trending Stories

1

Jennie Garth Briefly Addresses Dan Schneider & Costar Amanda Bynes

2

Travis Kelce Reveals His Not-So-Cruel Summer Plans With Taylor Swift

3

Why Paris Hilton and Carter Reum Don't Share Photos of Daughter London

Instagram/Rachel Bilson

This was not the first time Rachel got candid about the ups and downs of dating in Hollywood. Previously, the actress shared that she had to break up with Bill Hader over the phone because they couldn't do it in-person due to the pandemic.

"It was during a time where you could not leave your house," she told Call Her Daddy last year. "You had to sit in whatever it was that you were going through. So, I had to deal with this, I had to deal with being alone and taking care of my kid and everything else."

And, on her own podcast, Rachel had a very NSFW response when it came to what she missed most about her short-lived relationship with the Barry actor. "His big dick!" she quipped in an August 2022 episode, adding to her producer at the time, "You can keep that. Oh, that's funny."

For more OMG confessions from Rachel, keep reading.