Justin Timberlake’s beautiful women: Britney Spears, Fergie, Jenna Dewan, Alyssa Milano, Cameron Diaz and Jessica Biel

Choose your favorite pair. InRumor challenges you to choose the best match for Justin Timberlake. Voting is open until Sunday.

Britney Spears

Justin Timberlake dated Britney Spears from 1998 to 2002. They met at the Mickey Mouse Club at the age of 12.

This high-profile celebrity relationship ended in March 2002, following rumors of Spears’ infidelity with choreographer Wade Robson, a mutual friend of the two.

Timberlake’s hit “Cry Me A River,” one of the most popular singles from the album Justified, was influenced by the breakup.


Fergie and Timberlake had a short-lived romance in February 2004.

However, rumors say he was involved with the Black Eyed Peas singer prior to 2001 as well.

Jenna Dewan

Timberlake was romantically linked with professional dancer Jenna Dewan from Dallas in 2002.

Jenna performed with Justin at the 2002 Grammys to the N’Sync hit, “Girlfriend.”

In 2003 Timberlake reportedly sacked Dewan from dancing on his tour, as he didn’t want her to affect his performance. “Justin just couldn’t face the prospect of getting up close and personal on stage with his old flame,” a source said. “He was worried it might affect the whole performance.”

Alyssa Milano

Justin and Alyssa briefly dated in 2002.

The two had known each other for many years. When Justin broke up with Britney, he naturally turned to his best friend for comfort. But that friendship gradually made room for love, despite their age difference: Alyssa was nine years his senior.

However, even before she could tell Justin that she was leaving, the paparazzi took her by surprise when she was spotted with a new love interest in a Los Angeles bar.

Milano is currently married to David Bugliari. They are expecting their first child, a baby boy.

Cameron Diaz

Justin and Cameron were a couple from 2003 to 2007. Their relationship was kept secret in the first months.

They began dating soon after they met at the Nickelodeon Kids’ Choice Awards in April 2003. The tabloid press often reported stories of them having split, but they kept ignoring the gossip.

On December 2006, the couple split.

Jessica Biel

Jessica Biel and Justin Timberlake formed a wonderful couple from 2007 to 2011.

In 2007 romantic pictures of Justin and Jessica surfaced on the net. In addition, in the August 2008 issue of Heat magazine Timberlake was asked to describe his perfect woman, and he replied “About 5ft.7in.-5ft.8in., nice butt, Midwestern American, kind-of-German last name, green eyes, big pouty lips, fair skin, ahhh….sinewy bod…”

After four years together, the couple broke up in March 2011.

[poll id=”210″]