Rachel Bilson Recalls Her ‘Embarrassing’ Try at Flirting With Justin Timberlake
Rachel Bilson was a huge Justin Timberlake fan. Therefore, she went all in when she got the chance to shoot her shot with the triple threat in the early 2000s. However, her attempts at flirting turned “embarrassing” instead of romantic.
Rachel Bilson’s flirty actions toward Justin Timberlake didn’t go as planned
In an interview for her and Olivia Allen’s podcast Broad Ideas, Rachel Bilson discussed a moment with Justin Timberlake she would rather forget. The Accused star admitted she tried flirting with the superstar, but things didn’t exactly go as planned.
“In our day, [Timberlake] was very big, right? Like, the biggest. Sorry, no disrespect — he’s still very big,” Bilson said.
“We were all at a party or something, and he was there, and I was so obsessed with him,” Bilson continued. “[Bilson] went up to him, obviously, or he came to [Bilson],” Allen said. “I got drunk and embarrassed myself a little because he was trying to flirt with Rachel.”
However, Allen, who admittedly was drunk during the encounter, sat down between Timberlake and Bilson just as they hit it off. “I was just drunk and wanted to keep talking to him,” Allen claims.
After Bilson told Allen there was “no room” for her between them, she squeezed herself between them, trying to win Timberlake’s attention. Nonetheless, nothing happened between Timberlake and Bilson that fateful evening.
Did Rachel Bilson and Justin Timberlake ever date?
Alas, Rachel Bilson and Justin Timberlake never actually dated. Their flirtatious encounter remained just that.
Justin Timberlake did, however, date a who’s who of the entertainment world’s most popular beauties. He dated Britney Spears from 1999 to 2002. Following were Jenna Dewan, Alyssa Milano, and Cameron Diaz.
He and Jesica Biel made their relationship public in January 2007. They split in March 2011 before reconciling the following July. The pair got engaged in January 2012 and exchanged vows in October 2012 in Italy. They are the parents of sons Silas and Phineas.
Rachel Bilson famously dated her OC co-star Adam Brody throughout the series run from 2009-2007. She met Star Wars actor Hayden Christensen on the set of the 2008 film Jumper.
The couple dated for 10 years and welcomed one daughter, Brian Rose, in 2014. They split in 2017.
Since then, Bilson has been linked to Bachelor star Nick Viall. She also dated Barry star Bill Hader for two years.
Rachel Bilson won’t name who she’s currently dating
In an August 2022 interview for the podcast Call Her Daddy, Rachel Bilson admitted she was no longer single. This admission came two years after breaking up with Bill Hader.
“This is a generalization,” she teased. “I think I’ve dated quite a few actors, and I do think that some of them, not all, have very self-involved tenancies.”
She continued, “I think that just comes along with the territory a lot of the time. I’m not saying all of them I’ve dated have them, but it is a theme. And I don’t like it.”
The podcast’s host, Alex Cooper, asked Bilson, “Are you currently single?” The actor replied, “I am not.”
Cooper then jokingly inquired, “Is he bringing you coffee in the morning?” She replied, “F*** yea.”
The actor did not confirm who she was dating. However, Bilson was seen showing PDA on the beach in May 2023 with artist Zac LaRoc.
