{"id":81512,"date":"2023-09-28T20:21:37","date_gmt":"2023-09-28T10:21:37","guid":{"rendered":"https:\/\/graziamagazine.com\/?post_type=articles&p=240473"},"modified":"2023-09-29T07:03:32","modified_gmt":"2023-09-29T07:03:32","slug":"rachel-bilson-justin-timberlake","status":"publish","type":"articles","link":"https:\/\/graziamagazine.com\/us\/articles\/rachel-bilson-justin-timberlake\/","title":{"rendered":"Rachel Bilson Recalls Her \u201cEmbarrassing\u201d Attempt To Flirt With Justin Timberlake"},"content":{"rendered":"
\"rachel-bilson\"
LOS ANGELES, CALIFORNIA – OCTOBER 21: Rachel Bilson attends the Fifth Annual InStyle Awards with FIJI Water on October 21, 2019 in Los Angeles, California. (Photo by Charley Gallay\/Getty Images for FIJI Water)<\/figcaption><\/figure>\n

In the early-to-mid 2000s, Rachel Bilson<\/a> was living out her life as Summer Roberts, the fast talking, overly particular significant other of Seth Cohen<\/a> in Josh Schwartz’s teen drama mega-hit The O.C.<\/a><\/em> It was right around the time Justin Timberlake was at his career peak<\/a>, too: \u201cSe\u00f1orita\u201d, \u201cSexyBack\u201d, \u201cCry Me A River\u201d, the list went on.<\/p>\n

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.<\/p>\n

\u201cIn our day, [Timberlake] was very big, right? Like, the biggest. Sorry, no disrespect \u2014 he\u2019s still very big,\u201d Bilson detailed on Broad Ideas<\/em><\/a>, a podcast she hosts with Olivia Allen, a friend who was also at the same party on that now infamous night. \u201cWe were all at a party, or something, and he was there, and I was so obsessed with him.\u201d<\/p>\n

\"rachel-bilson\"
Mischa Barton and Rachel Bilson during Motorola Hosts 5th Anniversary Party Benefiting Toys for Tots – Inside at 3526 Hayden in Culver City, California, United States. (Photo by Jeff Kravitz\/FilmMagic, Inc)<\/figcaption><\/figure>\n
\"rachel-bilson\"
NETHERLANDS – DECEMBER 28: Photo of Justin TIMBERLAKE; 28-12-2003 Arnhem, Justin Timberlake (Photo by Paul Bergen\/Redferns)<\/figcaption><\/figure>\n

While the duo really hit it off and were talking and flirting, Allen recounts how she ruined Bilson\u2019s chances of ever being with Timberlake.<\/p>\n

\u201c[Bilson] went up to him, obviously, or he came to [Bilson],\u201d Allen said. \u201cI got drunk and embarrassed myself a little because he was trying to flirt with Rachel\u2026I was just drunk and wanted to keep talking to him.\u201d<\/p>\n

Bilson recalls how Allen \u201csqueezed herself\u201d between the actress and singer on a tiny couch \u201cwith no room\u201d just so that she herself could get Timberlake\u2019s attention.<\/p>\n

\u201cThe next time I saw him [out], he was like, \u2018What\u2019s up, enemy?’\u201d Allen laughed.<\/p>\n

The *NSYNC alum, 42, went on to marry 7th<\/sup> Heaven<\/em>\u2019s Jessica Biel<\/a> in 2012. The couple now have two children: Silas, 8, and Phineas, 2. The Hart of Dixie<\/em> star, who was linked to Gossip Girl<\/em> star Chase Crawford<\/a> and recently dated funny man Bill Hader,<\/a> 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<\/em> star Hayden Christensen.<\/p>\n

Ah, a sliding doors moment, really. Imagine what could have been.<\/p>\n","protected":false},"author":27,"featured_media":81513,"template":"","format":"standard","categories":[23,16],"yoast_head":"\nRachel Bilson Recalls \u201cEmbarrassing\u201d Flirt With Justin Timberlake<\/title>\n<meta name=\"description\" content=\"When Rachel Bilson wound up at the same party as Justin Timberlake one evening in the mid 2000s, she tried to shoot her shot.\" \/>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/graziamagazine.com\/us\/articles\/rachel-bilson-justin-timberlake\/\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Rachel Bilson Recalls Her \u201cEmbarrassing\u201d Attempt To Flirt With Justin Timberlake\" \/>\n<meta property=\"og:description\" content=\"When Rachel Bilson wound up at the same party as Justin 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