Who Has Justin Timberlake Dated?

1 Fergie

After relationships with high school girlfriend Danielle Ditto and Innosense singer Veronica Finn, Justin struck up a brief romance with Fergie between 1996 and 1997; she was then part of the girl group Wild Orchid and going by her birth name, Stacy Ferguson. Fergie told Australia's Courier Mail, "He was 16 and I was 23. It was before he got real heavy with Britney."

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2 Beyoncé

Image Source: Getty / Kevin Mazur

While never confirmed, Justin and Bey were rumored to have shared some kisses during an industry party during their *NSYNC and Destiny's Child days. The reported hookup would have happened around 1998, before Beyoncé started dating JAY-Z.

Justin and Beyoncé have collaborated several times since then — as have Justin and Jay, who even went on tour together in Summer 2013 — and they've hung out at a handful of award shows as a foursome with Jessica Biel as well.

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3 Britney Spears

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Britney and Justin spent their childhood together while working on The Mickey Mouse Club and both went on to become pop sensations. They began dating in 1999 though didn't officially confirm the relationship until a year later. In 2002, they parted ways amid rumors of infidelity on Britney's side (Wade f*cking Robson, seriously?), leaving us with multiple cryptic breakup songs and one of the most iconic red carpet fashion moments of the decade.

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4 Jenna Dewan

Image Source: Getty / Frank Micelotta Archive

After his split from Britney in 2002, Justin moved on with Jenna Dewan, who was also one of his backup dancers at the time. Jenna opened up about their brief romance during a 2017 interview, saying, "We dated, not that long," adding, "We were like friends . . . that dated."

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5 Alyssa Milano

Image Source: Getty / Gregg DeGuire

Also in 2002, Justin dated the Charmed actress. In 2015, she told ET that despite her romance with the singer, she still felt that he and Britney were "super cute [and] super in love" and that "they just seemed like the perfect match."

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6 Tatyana Ali

Image Source: Getty / John Shearer

Justin had a blink-and-you-missed-it romance with the Fresh Prince of Bel-Air star in 2003.

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7 Cameron Diaz

Image Source: Getty / Lisa Blumenfeld

Justin and Cameron started dating in 2003 and called it quits in 2006 after almost four years together. Not long after breaking up, they had to walk the red carpet together to promote Shrek the Third, in which they both voiced characters. In addition to their animated reunion, Justin and Cameron teamed up again to play love interests in 2011's Bad Teacher (they even filmed sex scenes). About working with her ex, Cameron told Us Weekly, "Justin and I have always had a good laugh together, and there really was no one else who was more perfect for this part," adding, "It really wasn't a big deal, we had a great time and did the job, and we do what all actors do afterward: We all go our separate ways. We'll all come back together for the premiere."

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8 Kate Hudson

Image Source: Getty / Kevin Winter

Justin was reported to have hooked up with Kate Hudson at a New Year's Eve party in early 2007, just days after his split from Cameron. The romance was rumored to have upset Cameron so much that she "retaliated" in May 2010 by dating Yankees player Alex Rodriguez, who had dated Kate for several months the year before.

Though Kate was reportedly "pissed," it seems as though the two actresses have since made up; they were seen hanging out at Vanity Fair's annual Oscars afterparty in 2012, and in a 2013 interview, Cameron referred to Kate as her "good friend."

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9 Scarlett Johansson

Image Source: Getty / Kevin Winter

Justin cast Scarlett as his love interest in the 2006 video for "What Goes Around Comes Around," and the two were rumored to have hooked up on set. Scarlett was between relationships at the time; she had just broken up with Josh Hartnett and would go on to date (and marry) Ryan Reynolds

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10 Jessica Biel

Image Source: Getty / Larry Busacca

Justin and Jessica originally began dating in 2007 but split up in 2011 because they "realized they wanted different things in life and were headed in different directions." There were persistent rumors that Justin had cheated with actress Olivia Munn, but according to a source, "There was never any proof. When you're in a relationship, you have to choose to believe the person or get out."

Their breakup was short-lived: Jessica and Justin reunited and got engaged in 2012. They were married that October in Italy and welcomed their first child, son Silas, in April 2015.

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