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It’s Gonna Be Me! Justin Timberlake Relationship Timeline Revealed!

Cameron Diaz and Justin Timberlake in a scene from their movie Bad Teacher.
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Oct. 15 2020, Updated 3:03 p.m. ET

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When it comes to chronicling the Justin Timberlake relationship timeline, his romantic partners are a varied bunch. There are actresses (Cameron Diaz), singers (Britney Spears), an iconic sitcom star, a girl group leader, a dancer/actress and even the child of a Hollywood legend.

MORE: The 29 oddest celebrity couples of all time!

Of course, Timberlake is married to Jessica Biel, and they have a little one to make the Timberlakes a family of three. But before he headed down the aisle and “settled down,” he had been on the arm of some of Hollywood’s most gorgeous gals. There’s even an actress who grew up in front of our eyes on television and now has become a powerful voice in the #MeToo movement.

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MORE: 25 Couples who pulled off the impossible, they got married in secret ceremonies!

The man who brought “Sexy Back” certainly had a lot of practice with these lovely ladies. Read on to get the lowdown on what amounts to a Timberlake “top 10.”

1996-1997: Fergie

//justin timberlake dating history fergie
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The future Black Eyed Peas singer, who was then singing with an all-girl group called Wild Orchid at the time, dated Timberlake for about a year. Fergie was going by her given name then, Stacy Ferguson, and was seven years his senior when the two were an item. Age didn’t derail them — aspiring careers were thought to be the culprit in their breakup.

1998: Beyoncé

Beyonce dazzled in a low cut gold shimmery dress while Justin Timberlake wore a shiny black suit as the two sang onstage.
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Think Timberlake had a thing for singers? Although neither ever confirmed it, the “Cry Me a River” singer was said to have hooked up with Beyoncé while he was beginning his run in NSYNC, and she was part of Destiny’s Child, according to PopSugar.

1997-1998: Veronica Finn

The girl group Innosense featured singer Veronica Finn (closest to the camera) in a sleeveless, belly-exposing shirt and matching pants.
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Timberlake was 17 when he and singer Veronica Finn, who was a year his junior, dated for about a year and a half. She was part of the girl group Innosense, while he was — of course — anchoring the boy band NSYNC. It’s admirable that Timberlake would commit to trying to make a relationship work while his star was ascending into the stratosphere. Both singers had tough schedules but managed to make it work, until they couldn’t.

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Early 1999-March 2002: Britney Spears

Justin Timberlake sported a multi-colored oxford shirt while Britney Spears wore a ruffled beige dress.
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The relationship made in teen music heaven. That’s one way to describe the romance between the Tennessee native and the “Oops!... I Did It Again” hitmaker. The pair met while starring in the Orlando-based revival of The Mickey Mouse Club (an ensemble that also featured Ryan Gosling and Christina Aguilera) but didn’t start dating until each shot hits up the Billboard charts. Three years after they first hooked up, they split. At the time, no reason was given. Since then, speculation ran rampant that one or the other (or both!) cheated. “What Goes Around … Comes Around” by JT was rumored to be written about Spears’ unfaithfulness, as reported on MTV.

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2002: Jenna Dewan

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Jenna Dewan walked the red carpet in a floral strapless dress for the GQ Men of the Year Awards.
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Although it was brief, the superstar singer/actor dated dancer (and future actress) Jenna Dewan when she was Timberlake’s backup dancer. She visited Watch What Happens Live With Andy Cohen, and as the Bravo host is known to do, he got some dirt on her past. “We dated, not that long,” she admitted on the hit show (quoted on Entertainment Tonight). “We were like friends ... that dated."

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2002: Alyssa Milano

//justin timberlake dating history alyssa milano
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Alyssa Milano was starring on Charmed when she and the Rock Your Body singer dated briefly for merely a few months. Milano told ET that she and Timberlake did hook up, but she was keenly aware that his heart (and head) were still firmly swept up in Spears. “They just seemed like the perfect match!” Milano said to ET in 2015.

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2003: Tatyana Ali

Tatyana Ali made a colorful splash at the NAACP Image Awards in an artistic color spectrum that included purple and pink.
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Tatyana Ali and the “Suit & Tie” hitmaker dated so briefly in 2003 that it probably lasted less time than the theme song to her hit show, The Fresh Prince of Bel-Air.

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April 2003-December 2006: Cameron Diaz

Cameron Diaz and Justin Timberlake walked the red carpet for Bad Teacher. Diaz dazzled in a short black sleeveless dress, while Timberlake was dapper in a grey blazer over a V-neck sweater-shirt.
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Just as Timberlake started his foray into film, he met and started to date an actress — Cameron Diaz. The pair could not have met at a more family-friendly place, the Nickelodeon Kids’ Choice Awards. They got serious quickly and people speculated that the pair might even take the leap into marriage, but they didn’t. A few years later, the pair had to work together in the comedy Bad Teacher in 2011 — even portraying love interests and had to film a sex scene together. Diaz said that she and Timberlake dealt with it like the professionals that they are. "It really wasn't a big deal,” Diaz told Us Weekly. “We had a great time and did the job. 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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2006-2007: Kate Hudson

At the 2010 SAG Awards, Justin Timberlake wore a black suit with a black bow tie while his fellow presenter, Kate Hudson, dazzled in an open back white Emilio Pucci gown.
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At a New Year’s Eve party, merely days before he would connect with his future wife, Timberlake and Kate Hudson reportedly hooked up. It was just days after he had split with Diaz. According to E! Online, as 2006 turned to 2007, the actress — who has been involved with her share of singers (Chris Robinson, Nick Jonas, Matt Bellamy) — and the Suit & Tie vocalist rang in the new year with a bang.

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January 2007-Present: Jessica Biel

Jessica Biel and Justin Timberlake at the 2018 Emmy Awards with Biel donning a white strapless Ralph & Russo dress and Timberlake sporting a classic black tux with black bow-tie.
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The Golden Globes are notorious for celebrities knocking back champagne and letting loose. A couple of those celebs who enjoyed the party were Biel and JT. It was the 2007 Globes that found the pair first hooking up. And although they have been together ever since, even marrying and having a child, it wasn’t always smooth sailing for this pair. For example, in January of 2011, rumors scorched celeb news outlets that the Sexy Back singer was getting sexy with actress/host Olivia Munn. JT’s rep denied the rumors. They stayed together through the raging rumors, but by March it proved too much for Biel and she called it quits. During that short “break,” Timberlake starred opposite Mila Kunis in Friends with Benefits. Some have speculated that the two actors’ chemistry was so hot onscreen because it was equally as smoldering off the screen. The two denied those reports, even though photogs caught Kunis and Timberlake out with the singer’s folks. But by the end of 2011, Timberlake had popped the question to Biel, and on October 19, 2012, they made it official and got married in Italy. They are now parents to a little boy named Silas, born in April of 2015.

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