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In the early-to-mid 2000s, Rachel Bilson was living out her life as Summer Roberts, the fast talking, overly particular significant other of Seth Cohen in Josh Schwartz’s teen drama mega-hit The O.C. It was right around the time Justin Timberlake was at his career peak, too: “Señorita”, “SexyBack”, “Cry Me A River”, the list went on.
So, when Bilson wound up at the same party as Justin Timberlake one evening all those years ago, she, well, tried to shoot her shot.
“In our day, [Timberlake] was very big, right? Like, the biggest. Sorry, no disrespect — he’s still very big,” Bilson detailed on Broad Ideas, a podcast she hosts with Olivia Allen, a friend who was also at the same party on that now infamous night. “We were all at a party, or something, and he was there, and I was so obsessed with him.”
While the duo really hit it off and were talking and flirting, Allen recounts how she ruined Bilson’s chances of ever being with Timberlake.
“[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…I was just drunk and wanted to keep talking to him.”
Bilson recalls how Allen “squeezed herself” between the actress and singer on a tiny couch “with no room” just so that she herself could get Timberlake’s attention.
“The next time I saw him [out], he was like, ‘What’s up, enemy?’” Allen laughed.
The *NSYNC alum, 42, went on to marry 7th Heaven’s Jessica Biel in 2012. The couple now have two children: Silas, 8, and Phineas, 2. The Hart of Dixie star, who was linked to Gossip Girl star Chase Crawford and recently dated funny man Bill Hader, is now dating a man who brings her coffee in the morning. She is mother to her eight-year-old little girl, Briar Rose, whom she co-parents with former partner Stars Wars star Hayden Christensen.
Ah, a sliding doors moment, really. Imagine what could have been.
