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March 10, 2011: After four years of dating, Justin and Jessica break-up on mutual terms and remain good friends.June 2007: Even though, at the time, the pair were off-again, Timberlake tells , "[Jessica] is the single-handedly most significant person in my life." September 2011: The pair makes time for an intimate dinner as Biel attends Timberlake's Shriners Hospital for Children golf event. Justin and Jessica are spotted on a double date with Timberlake's parents in Los Angeles.The pair are spotted getting cozy in Manchester at a football match.October 2008: The couple that votes together, stays together? Justin and Jessica show their support for Obama at a rally in Las Vegas.Close to 15 years later, fans still have fond memories of the pair who defined young love and made matching denim-on-denim looks iconic on the red carpet.

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Justin Timberlake: The two former Mouseketeers started dating in 1999 and ended their relationship in 2002.Long before he was JT and waaay before she was rockin' it out onstage with the Black Eyed Peas, the pair were an item.He was 16 and just starting out in 'N Sync, she was 23 and one-third of the pop trio, Wild Orchid -- talk about robbing the cradle! They grew up together on the Disney show, and began a romance in 1999.December 2008: Jessica tells the UK edition of , "Justin Timberlake is the one part of my life that I own." And how does JT feel about that, Jess?February 2010: Jessica tells Vogue that Timberlake is "the most precious thing I have in my life." January 2011: After reports that Justin cheated on Jessica with Oliva Munn in October 2010, rumors surface that the "Sexy Back" singer was continuing to carry on a textual relationship with the up-and-coming actress.However, before JT settled down with the 33-year-old actress and his new family, the former N’Sync singer for sure had his share of relationships with some of Hollywood’s leading gals.To celebrate the latest chapter in Timberlake’s life, let’s look back at all the women he said “Bye Bye Bye” to for good.To honor JT's special day, we're taking a look back at all of his high-profile romances.Let's just say he had a lot of practice in the relationship field before putting a ring on Jessica Biel's finger!star are in full parent mode with their new bundle of joy, Silas Randall.The 34-year-old singer first announced the pregnant news back in January and couldn’t hide his excitement since.

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