A Look Back At Justin Timberlake's Dating History Before Jessica Biel

In 2012, Hollywood heartthrob Justin Timberlake married actor Jessica Biel in an intimate Italian ceremony. "I had a little bit of butterflies," Biel admitted to People at the time. "I was about to stand up in front of my friends and family and bare my soul for the person I love. It was terribly emotional." But of course, the pair's fairytale had been a long time coming.

Timberlake and Biel first sparked relationship rumors in January 2007 after they were spotted snowboarding together in Utah. Though sources insisted the pair were just friends at the time, things soon took a romantic turn. In December 2011, Timberlake popped the big question, getting down on one knee during a trip to Montana. "We had snowboarded all day. It was in the middle of the winter. Waist-high snow. We were [in] head-to-toe snowboarding outfits — hats, gloves, everything. And all of a sudden, he gets down onto his knees and just sinks into the snow," the "7th Heaven" star recounted to People.

Since getting married, Timberlake and Biel have welcomed two sons together, with their love waxing stronger by the year. "10 years ain't enough!" the singer wrote alongside a series of throwback shots of the two on their 10th anniversary. "You make me a better husband and father every day! I love you so much you beautiful human! Run it back!" But while Timberlake is no doubt living his happily-ever-after, before Biel, the "Mirrors" singer had racked up a pretty interesting dating history.

Back in the '90s, Justin Timberlake enjoyed a brief romance with singer Stacy Ann Ferguson, popularly known as Fergie. In an interview with Courier Mail, Fergie confirmed the relationship, revealing that she was 23 and Timberlake was 16 at the time of their romance. "It was before he got real heavy with Britney," she added (via US Weekly). 

But while Timberlake and Fergie's romance made headlines at the time, the "Life Goes On" singer insists it was only a fling. "One of my good friends was dating J.C. Chasez, and so we'd all hang out with *NSYNC. Justin and I would go out together and have fun and make out. We went to Hawaii together, but we were never serious," she told Cosmopolitan back in 2006.

Britney Spears and Justin Timberlake publicly dated for three years, between 1999 and 2002. During their time together, Spears and Timberlake reigned as one of Hollywood's most beloved pairs, but eventually, their tumultuous love story unraveled. In her 2023 memoir "Woman In Me," Spears accused Timberlake of cheating on her while admitting to having an abortion during their time together. "If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn't want to be a father," she wrote of the experience. In the book, Spears also accused the "Mirrors" singer of breaking up with her over text. "It's over!!!" the text reportedly read, according to Page Six.

Following his split with Britney Spears, Justin Timberlake briefly dated Jenna Dewan, who was working as his backup dancer at the time. During a 2017 appearance on "Watch What Happens Live with Andy Cohen," Dewan opened up about her time working for the singer while confirming their rumored romance, saying, "Um, yeah. We dated. Yeah. Yeah, we dated. Not that long. We were like friends — friends! — that dated." And while rumors have hinted at Dewan only being a rebound for Timberlake, the "Step Up" actor says she was not. "I was not the rebound! I was very clear not to be [that]. ... We're still very good friends. It's not as salacious as everyone thinks," she added.

Justin Timberlake also had a short-lived romance with star Alyssa Milano. In a 2016 interview with Rove&Sam, Timberlake admitted to having a crush on the "Who's the Boss?" actor. "My big crush ... was Sam in 'Who's the Boss' ... Alyssa Milano," he shared on the show. However, according to Timberlake, things between him and Milano got weird after their brief relationship in 2002. "I was like "hey, I used to be obsessed with you when I was a kid," he shared.

And despite her history with Timberlake, Milano was one of the many rooting for the singer's love story with Spears. "They just seemed like the perfect match!" the "Charmed" star gushed to ET in 2015.

In 2003, Justin Timberlake started dating Cameron Diaz, whom he first met at the 2003 Nickelodeon Kids' Choice Awards. Despite a nine-year age gap, the couple went on to be together for nearly four years before breaking up in January 2007. "We have, in fact, ended our romantic relationship, and have done so mutually and as friends, with continued love and respect for one another," Diaz and Timberlake shared in a joint statement to People. 

Despite their short-lived romance, Timberlake and Diaz have gone on to maintain a cordial relationship, with the pair reuniting in 2011 to star in "Bad Teacher," a comedy flick featuring other stars like Jason Segel and John Michael Higgins. "He's clearly talented. We went for the best person for the job, and it just so happened that it was him. And he delivers," Diaz told US Weekly of her ex.