Who Has Justine Timberlake Dated In The Past? Exploring His Dating History Amid Rumors Of Divorce

Justin Timberlake, the multi-talented artist, has left an indelible mark on the entertainment industry. Beyond his chart-topping music career, Timberlake’s personal life has often captured public interest. He gained prominence as a member of *NSYNC and later transitioned seamlessly into a successful solo career. 

However, his relationships, including a high-profile romance with Britney Spears during their Mickey Mouse Club days, garnered significant attention. In 2012, Timberlake married actress Jessica Biel, and the couple welcomed their son Silas in 2015. Despite occasional tabloid scrutiny, Timberlake maintains a private stance on his personal life, focusing on his family and artistic endeavors.

Justin Timberlake’ past relationship timeline

Justin Timberlake, the ‘NSync frontman, navigated a complex dating history since his 1995 stardom. Amid high-profile relationships, including Britney Spears and Cameron Diaz, he ultimately found lasting love with Jessica Biel in 2012, overcoming rumored romances during their journey. Here’s the list of Timberlake’ ex’s.

Britney Spears

The iconic relationship of Justin Timberlake and Britney Spears defined the early 2000s with memorable moments and public intrigue. Meeting in 1992 on the set of the Mickey Mouse Club, their connection deepened when Britney opened for NSYNC in 1998. Confirming dating rumors in 2000, they became a power couple, living together by 2001. However, their union faced turbulence and ended in March 2002. Speculation arose with Justin’s release of Cry Me a River, hinting at infidelity, though he later clarified it was a creative expression of his emotions. The aftermath remained shrouded in mystery until Britney’s 2023 memoir, revealing a poignant detail, she had an abortion while dating Timberlake, a decision influenced by his unpreparedness for fatherhood.

She wrote in her memoir, “It was a surprise, but for me, it wasn’t a tragedy. I loved Justin so much. I always expected us to have a family together one day. This would just be much earlier than I’d anticipated. But Justin definitely wasn’t happy about the pregnancy. He said we weren’t ready to have a baby in our lives, that we were way too young.”

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Cameron Diaz

Justin Timberlake and Cameron Diaz’s romance sparked at the 2003 Kids Choice Awards, where she presented him with Best Burp, says InStyle. Despite their nine-year age gap, the couple embarked on a nearly four-year relationship. However, their union faced persistent rumors of infidelity, reaching a climax with a public spat at a Golden Globes after-party in January 2007, as per People. The speculation surrounding their fidelity contributed to the eventual end of their relationship.

Witnesses recounted a dramatic episode during a Golden Globes after-party, revealing that Cameron Diaz became upset upon seeing Justin Timberlake engaged in conversation with his future wife, Jessica Biel. The tension escalated into an “intense 40-minute face-off in a side room”. Although Diaz exited the room seemingly composed, Timberlake, visibly affected, reportedly expressed his frustration by “slamming his fist into a cabinet”, as observed by onlookers.

Rumored exes of Justin Timberlake

In a 2017 episode of Watch What Happens Live with Andy Cohen, Fergie candidly admitted to a brief involvement with Justin Timberlake during a game of Plead the Fifth, downplaying its significance with a casual remark, “it wasn’t all that serious,” and a roll of the eyes. However, she chose to keep certain details under wraps.

 

Also, The U.S. Sun has claimed that Justin Timberlake had alleged flings with various celebrities, including Emma Bunton (Baby Spice), Beyoncé, Scarlett Johansson, and Alyssa Milano. Emma Bunton, responding to the rumors, mentioned, “We hung out and partied a bit and he was very sweet,” as per People.

ALSO READ: How Did Justin Timberlake and Jessica Biel’s Relationship Progress Over The Years? See The Timeline Here Amid Divorce Rumors

Are Justin Timberlake and Jessica Biel divorcing?

Justin Timberlake and Jessica Biel’s marriage is reportedly on the brink of dissolution, and attempts to salvage it through couples therapy have proven unsuccessful. An exclusive source informed Life & Style, “Rumors are swirling that he and Jessica are headed for a split. Though they do love each other, all of the couples therapy they’ve undergone simply isn’t fixing some of their underlying issues.”

Speculation about the impending split has been fueled by the couple’s recent real estate transactions, suggesting potential financial restructuring. Friends close to them have interpreted these moves as a signal that they are taking steps to get their finances in order. The couple, who tied the knot in 2012 and share two children, Silas, 8, and Phinneas, 3, have also sought refuge in a Montana home at one point. The insider told, “At one point, they retreated to another home, in Montana, in the hopes of getting away from drama and starting over, but you can’t run away from your problems.”  

Timberlake and Biel have a history of splitting in the past. After dating for four years, the couple went their separate ways in 2011, only to reconcile and get engaged later that same year. However, this time around, the possibility of a permanent split is looming, according to an insider who remarked, “A split could be for good” as they find themselves at a crucial “crossroads” in their relationship.

The source revealed that “Britney’s book revelations brought up more of Jessica’s trust issues”, creating additional strain in their marriage. Despite attempting to present a united front at a Trolls Band Together screening on November 16, 2023, immediately following the release of Britney’s tell-all, the insider noted “but everyone thought it was super calculated. The truth is, Jessica is tired of trying to get past things with Justin.”

Currently, the couple finds themselves in a “wait-and-see” situation, as “nobody wants a divorce. Justin and Jessica have two great kids, and they’d love to make it work — it just may be too late.”

ALSO READ: Are Justin Timberlake And Jessica Biel Headed For Divorce? Insider Says ‘They Appear To Be At A Crossroads’