Rachel Bilson Once Made An Awkward Attempt To Flirt With Justin Timberlake

Justin Timberlake may now be all loved up with his wife, Jessica Biel, but it turns out there's another former teen drama icon he could have ended up with had it not been for a terrible wingwoman. Former "The O.C." star Rachel Bilson once had a failed flirt with the hitmaker years before he got together with the ex-"7th Heaven" actor — and she shared all the details of the super awkward encounter on her podcast.

Bilson explained on "Broad Ideas" that she and Timberlake were at the same party back in the 2000s, and she took her opportunity to shoot her shot with the *NSYNC singer, whom she had a major crush on. Bilson's close friend and podcast co-host, Olivia Allen, was also there, and she recalled that the incident went down when she and Bilson were both hanging out with Timberlake and trying to get to know him.

"[Bilson] went up to him, obviously, or he came to [her]. I got drunk and embarrassed myself a little because he was trying to flirt with [her]," Allen shared. She explained that instead of being a good wingwoman to her bestie and leaving the two alone to chat, she ended up sitting right in between the two, even though there was hardly any room. "I was just drunk and wanted to keep talking to him," Allen recalled. "There was no room. Olivia planted herself [between us], squeezed herself [in]," Bilson added (via HuffPost).

Olivia Allen then joked on "Broad Ideas" that Timberlake wasn't too annoyed about the awkward interaction but noted Bilson might have been at the time. But just because Timberlake let the moment go, that doesn't mean he didn't remember the fail. Allen revealed that she went on to run into the "Cry Me A River" singer again afterward when he jokingly asked her, "What's up, enemy?" But while Bilson may not have been too thrilled at the time over Allen thwarting her attempt to get closer to her crush, these two are clearly still close today. All's well that ends well, right?

It turns out that wasn't the only missed opportunity for Bilson and Timberlake to get close, though. There was a rumor floating around in 2004 that Timberlake may have been in talks to land a role on the second season of "The O.C." Teen Hollywood claimed that he was supposedly in the running for a recurring role as an unnamed bad boy character, but reported that Adam Brody, who played Seth Cohen on the teen hit, wasn't too thrilled about the idea of him joining the cast (via Digital Spy). Supposedly, Brody was worried about Bilson's crush on the actor and singer turning into something more, as he was dating her at the time. Bilson and Brody eventually split in 2006, and the rumor of Timberlake's role never came to fruition.

We already know that Rachel Bilson's attempts to flirt with Justin Timberlake didn't end well, and her romance with her "The O.C." co-star Adam Brody also ended in a split. But her interrupted chat with Timberlake and breakup with Brody clearly didn't put her off dating a celebrity.

Bilson went on to have a decade-long relationship with Hayden Christensen after they met while filming the movie "Juniper." The two welcomed a daughter together in 2014 but split in 2017 amid speculation he moved on with Emma Roberts. After that, Bilson got publicly flirty with former "The Bachelor" star Nick Viall. Viall shared a photo of himself and the actor together on Instagram after she appeared on his podcast in September 2019, writing in the caption, "Will we choose to forgo our individual rooms..." The quip was a reference to the notorious line uttered on "The Bachelor" franchise before a couple heads into the fantasy suite for an overnight date. Bilson then got flirty herself in the comments section, writing in a message that since appears to have been deleted, "He slid into her...dms #sheaccepted" (via People).

Things didn't exactly go the long haul there, though. The year after her flirtation with Viall, Bilson confirmed her romance with comedian Bill Hader when they attended the Golden Globes together in January 2020. However, by July 2020, the two had gone their separate ways.