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

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.

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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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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.”

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.

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.

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.

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."

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.

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!"

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.

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.