Justin Timberlake's Dating History

Justin Timberlake's dating history: From Britney Spears to Jessica Biel! 

Justin Timberlake kicked off his career with the long-disbanded boy group, NSYNC, in 1995. At its peak in the 90s, the band was one of the most loved teen bands. Following their split in 2002, all five members embarked upon their respective solo careers. While four of the five garnered limited success in their venture, Timberlake, the youngest of the five, reached an astonishing height in his career.  

Born on January 31, 1981, in Memphis, Tennessee, the once small-town boy has won ten Grammys in his two-decades-spanning career. Known for his ever-boyish charm and of course, his agile falsetto voice, Timberlake made a life-changing decision in his singing career when he sold his entire music catalog to Hipgnosis Song Management for $100 million last year.  

Inside Justin Timberlake's Dating History!  

Timberlake has dated a slew of A-listers in his dating career. Many of his famous relationships might have received an excessive amount of media exposure but some of them have also gone hardly unnoticed. Before he started his most iconic relationship with the Toxic hitmaker, the Friend with Benefits actor briefly dated singer Fergie in 1996.   

Justin was reportedly 16 when he romanced a 23-year-old Fergie. Timberlake's first high-profile romantic stint was with Britney Spears, a relationship that'll be remembered for a long time in pop culture even after it had ended. Justin started dating Spears in 1999. The duo had met when they were kids and members of The Mickey Mouse Club.  

During their nearly four-year-long relationship, Justin and Britney had many iconic moments, one of them being when Spears and Justin's NSYNC band, along with Aerosmith, played the Super Bowl halftime together. The fan-favorite couple split ways in 2002 amid the rumors that Spears had been unfaithful to Timberlake with choreographer Wade Robson.   

After his famous breakup with Spears, Justin's pairing with Jenna Dewan, and Alyssa Milano, went under the radar. It wasn't until over a decade later that both Dewan and Milano confessed to their little trysts with the Grammy-winning singer. Timberlake also famously dated actress Cameron Diaz.   

The Mirror crooner and Diaz's romance lasted nearly three years, from 2003 to 2006. The couple announced their breakup in early 2007. The swirling rumor at the time was that Timberlake had a thing going on with his What Goes Around... Comes Around music video co-star Scarlett Johanssen, who later refuted the claim.  

Inside Justin Timberlake's Conjugal Life with Jessica Biel!  

The ten-time Grammy winner has been married to actress Jessica Biel since 2012. It hasn't been all bed of roses or a smooth run but the pair are going strong still. The former NSYNC singer started dating Biel in early 2007. After three years of gushy romance, Justin, and Biel experienced their first bump as they announced their split in 2011.   

The rep for the pair asserted that the couple had decided on a cordial split, despite the circulating speculation that linked Justin with his Friends with Benefits co-star, Mila Kunis. "No one came between them. They decided their relationship ran its course and it was time to move on," said a source.  

The Cry Me a River hitmaker quickly rekindled his relationship with Biels within months of their breakup and by the year's end, Justin and Jessica were engaged. Recalling his sweet proposal to Biel during their romantic getaway in Montana, Justin said, "She is the single-handedly most significant person in my life."  

The couple tied the knot on October 19, 2012, in a secret ceremony in Southern Italy. They welcomed their firstborn, Silas Randall, in April 2015. The duo's marriage hit headlines in 2019 when the Grammy winner sparked cheating rumors with his Palmer co-star, Alisha Wainwright. In a viral pap-captured image, Justin was spotted holding hands with Alisha.  

"Nothing happened between me and my costar. I drank way too much that night and I regret my behavior," Timberlake said while debunking infidelity rumors. The couple welcomed their second kid, Phineas Timberlake, in January 2021.    

The long-married couple has weathered many bumps in their years of marriage, including an infidelity rumor!

The doting parents of two prefer to keep their kids out of the media's eye, they often give fans insights into their family life by sharing funny anecdotes, and parenting talks. "It's an amazing, amazing experience. Incredibly hard — the hardest job in the world, and I've never been more thankful and grateful to my own mother," said Biel, best known for her roles in Seventh Heaven, The Texas Chainsaw Massacre, and more.  

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