He said 'Bye, Bye, Bye' to Jenna Dewan and Alyssa Milano
If you were hoping for a Britney/Justin reunion, you were likely heartbroken when rumors started to fly that Justin was dating Jenna Dewan, who was coincidentally a backup dancer for N'Sync. (But it looks like things turned out OK for her... now, she's Mrs. Tatum.) Later that year, Justin dated actress Alyssa Milano, but their relationship only lasted a few months, which is a shame since they made a cute couple. Guess he wasn't too lucky in love that year.
He dated (and had some drama with) Cameron Diaz
Where else do you go looking for love except at a kids' awards show? Justin and Cameron Diaz met backstage at the Nickelodeon Kids' Choice Awards in April 2003 and apparently sparks flew. They dated for four years before rumors of infidelity and public spats began tearing them apart, and they finally called it quits in 2007. They went on to be costars in Bad Teacher and judging by that, um, really awkward sex scene, they wouldn't have made a very cool couple anyway. No love lost.
He jumped for joy over marrying Jessica Biel… literally.
It was a long up-and-down romance between Mr. and Mrs. Timberlake (better known as actress Jessica Biel) before they walked down the aisle. They were first spotted flirting at a Golden Globes after-party, then they were caught canoodling by the paparazzi. They finally admitted to their romantic relationship in the spring of 2007, only to break it off in the winter of 2011. They were on and off; but eventually got their act together and finally tied the knot last year. And who can forget that wedding photo on the cover of People? Totally priceless.
"I answer to a higher power now," Justin joked to Us Weekly. "We have a couple of rules in our relationship. The first rule is that I make her feel like she's getting everything. The second rule is that I actually do let her have her way in everything. And, so far, it's working."
As for the lucky lady herself, Biel remarked on The Ellen DeGeneres Show, "It just feels incredible. It feels like you have this partner who is going to be with you and also change light bulbs and do dishes with you."
We would give anything even to do dishes with JT, am I right ladies?