Who Did Justin Timberlake Date Before Jessica Biel?

Justin Timberlake is a very successful singer and entertainer. He was a member of the boy band group N’Sync before ultimately transitioning into his own career as a solo artist.

Timberlake is a noted heartthrob, and his posters have adorned the walls of many young girls all throughout the late nineties and into the 2000s. He’s also dated some of the most beautiful women in entertainment, including, of course, Britney Spears.

These days, Timberlake is married to the actress Jessica Biel — but his dating history reads like a who’s who of women in entertainment.

Justin Timberlake and Jessica Biel are a low-key couple

Justin Timberlake on the red carpet
Justin Timberlake | Jamie McCarthy/FilmMagic

In 2007, Justin Timberlake and Jessica Biel first crossed paths, reportedly during a snowboarding excursion. Only a couple of months after the two first met, reports started swirling that they were dating and completely smitten with each other.

Over the next several years, rumors would circulate that Timberlake and Biel were having problems but they continued to defy the odds and stuck it out.

Still, in early 2011, the couple broke up, only to reunite later that same year. This time, Timberlake wasn’t taking any chances of losing his dream girl, and proposed to Biel shortly after their reconciliation. In October 2012, the two tied the knot in a super-secret Italian ceremony.

Timberlake and Biel became parents in April 2015 when they welcomed their son, Silas Timberlake. While the couple has preferred to keep their marriage out of the headlines as much as possible, there was some controversy in late 2019 when Timberlake was spotted holding hands with a co-star.

Although he was quick to dismiss rumors that he had cheated on Biel, fans still wondered if there could be trouble in paradise. To this day, Biel and Timberlake seem to be going strong and are still married. 

Justin Timberlake’s romances post-Britney Spears

Before Justin Timberlake settled down with Jessica Biel, he dated several high-profile women. Although Timberlake was rumored to have dated Scarlett Johansson and Kate Hudson, neither of those romances were ever directly confirmed.

What was certain is that Timberlake had a long-standing romance with actress Cameron Diaz. The two started dating in 2003 and were together for nearly four years before ultimately breaking up in 2006. Still, the relationship was one of Timberlake’s longest and they seemed to truly have fun together. 

Prior to his romance with Diaz, Timberlake was spotted with actress Alyssa Milano and dancer Jenna Dewan. Although those rumored flings certainly made headlines at the time, the media coverage was nothing compared to the firestorm that Timberlake and his longtime love, Britney Spears, endured. 

How long did Justin Timberlake and Britney Spears date?

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They were the most popular couple of the late nineties and early 2000s, and for many, their love story defined an era. Justin Timberlake and pop princess Britney Spears started dating in 1999. They were both at the peak of their popularity as young pop stars and had been friends for years when they started dating.

Timberlake and Spears graced many a red carpet, and even performed together several times, inciting the crowds into a frenzy. 

Still, their love didn’t last forever and in 2002, the young couple broke up. While there were rumors of infidelity, nothing concrete ever surfaced and fans were left to wonder what exactly went on between the pair that had seemed so much in love.

Even today, although Timberlake is married and Spears is involved with a devoted boyfriend, some fans hold out hope for an eventual reunion for the onetime couple.