Rachel Bilson Reveals "Embarrassing" Flirting Attempt With Justin Timberlake

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.

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

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.

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.

Rachel Bilson wasn't afraid to make a shocking revelation about her sex life during a March 2023 episode of her Broad Ideas podcast, confessing that she had never experienced an orgasm from sexual intercourse until she was well into her 30s.

The reveal came after The O.C. star's guest Whitney Cummings shared that her sex drive had increased since going off birth control. "I have not had an orgasm from sex until I went off birth control," Cummings said. "Never had it in my life until I turned 40, but I could do it with my hands."

Bilson, 41, related to Cummings' experience, admitting that she didn't experience an orgasm until she was 38. "Isn't that crazy?"

Rachel⁠ also noted that she had previously gotten it done on her own, but "not with, like, dick inside."

Bilson continued to dish out bedroom confessions when she revealed her go-to sex position in a May 2023 episode of the Women On Top podcast.

"I've learned that if you want to have an orgasm during sex, you have to be on top," Bilson shared. "Missionary is my favorite. I want to be f--king manhandled."

The Jumper actress went on to reveal the position she tries to avoid is doggy style, with Bilson explaining that it depends on "the actual dick" because "it can go so deep and hurt."

Shortly after sharing her thoughts on sexual positions, Bilson revealed during the May 15 episode of Broad Ideas that she suffered professional fallout from her candid conversation.

"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," she explained, "I basically got a job, that I already had, pulled from me because I was speaking openly about sex."

Noting she was "floored" by the move, Bilson admitted losing the opportunity "sucks," but she didn't regret anything she shared.

"I haven't said anything inappropriate," she stressed. "Choice of language, if I could go back, now knowing I lost a job, maybe I would say it differently. But I still wouldn't not say it."

When asked what she missed most about ex-boyfriend Bill Hader, who she dated from late 2019 to the summer of 2020, Bilson made quite the large revelation.

"His big dick!" she quipped on her podcast's Aug. 15 episode, before adding to her producers, "You can keep that. Oh, that's funny."

While some stars try to keep details of their love life private, Bilson's never been one to shy away from talking about her romantic interests on her podcast.

In a June 2022 episode, the Hart of Dixie alum told her guest Aubrey Plaza that she and Hader had previously dated, which was a revelation to The White Lotus star despite the fact that the three actors had co-starred in the 2013 comedy The To-Do List. Bilson's response? "I went with him to the f--king Golden Globes."

During her intimate chat with Mandy Moore in a June 2022 episode of Broad Ideas, Bilson—who shares daughter Briar Rose Christensen, 8, with ex Hayden Christensen—opened up about "a really hard breakup" she endured during the pandemic without naming names. 

"I could not leave my house, you know what I mean?" she shared. "I had nothing else to do but sit in it, and deal with it and feel it. It was probably the hardest thing I've ever done⁠, harder than childbirth."

While Bilson added that the split "hurt like a motherf--ker," she explained that facing the breakup helped her move on. "You can come out of it and be like, 'Okay, I did that and I'm ready for the next thing.'"

While The O.C. fans were watching the love triangle play out between Summer, Seth (Adam Brody) and Anna (Samaire Armstrong) during the Fox teen hit's first season, Bilson revealed that there was romantic drama going down behind the scenes among the trio.

On the Welcome to The O.C., Bitches! rewatch podcast, she admitted she was "a little jealous" when Brody and Armstrong kissed in an early episode. 

"It was like the real-life triangle playing out as I'm watching it," Bilson, who dated Brody for several years before they broke up in 2007, recalled. "I feel like it definitely played out a little bit in real life for a minute, even though not really really. But I remember the tension with Samaire and I, like, a little bit."

Given that her mother Janice is a sex therapist, Bilson has always had a comfort level with discussions others may find uncomfortable. 

"Growing up in a household that was so sex-positive and free and candid...definitely made me more obviously open talking about things," she told Yahoo! Life's The Unwind series in July. "These are the things women go through, and there's nothing connected to it that feels like, 'Oh, I shouldn't be talking about this."

And it's why Bilson launched the Broad Ideas podcast with her best friend of 25 years, Olivia Allen, in 2022. On the show, she welcomes a variety of guests to discuss a range of broad topics, including sex, infidelity, and mental health, free of filters or fake niceties.

"I'm a little more unhinged, but it's nice to be able to feel free with it," Bilson told E! News at the time. "Authentic is the better word and I think people are craving it more than ever."

Explaining she wanted to provide a "safe space" for women to share their experiences, Bilson said she wanted the podcast to feel similar to a weekly hangout with "true friends" that don't judge one another. 

"It's just having these soul sisters that you can go through everything with that have been there through everything and will never judge you," she said. "It just felt like my best friends and I are always having these conversations, why not make that the norm?"