Before Justin and Britney got together, Timberlake reportedly dated Black Eye Peas singer Fergie when her former girl group Wild Orchid was opening for N’SYNC. She was 23 and he was just 16!
Young, beautiful, rich, A-list famous and wearing head-to-toe matching denim on the red carpet—ah, the magic of pop star love. Justin Timberlake and Britney Spears had a heavily publicized romance starting in 1999 and ending abruptly in 2002. Sometimes love, like fashion, doesn’t quite work out.
2002 was a busy year for Timberlake! The freshly single singer was linked to A-listers Janet Jackson and Alyssa Milano, along with N’SYNC backup dancer Jenna Dewan.
Almost a year after her breakup with Timberlake, Britney Spears reportedly dated Limp Bizkit bad boy Fred Durst in 2003—a rumor she denied and Durst adamantly confirmed. A month later, Spears was linked to actor Colin Farrell, but the Irish actor denied they were in a relationship.
In 2003, Justin Timberlake began dating actress Cameron Diaz—who is nine years older than him. Despite the age difference, the couple dated for four years before splitting in 2007.
After a sudden 55-hour marriage to childhood friend Jason Alexander, Britney Spears tied the knot with backup dancer Kevin Federline in 2004, having dating just three months. The couple had two children, a short-lived reality show and provided plenty of news for the press.
Shortly after his breakup with Cameron Diaz, Justin Timberlake began dating ‘7th Heaven’ actress Jessica Biel. The pair broke up in last March, but got back together a few months later. Good thing, since eventually Timberlake popped the big question to her. Hopefully the first time’s a charm for this A-list couple!
In 2010, Britney Spears confirmed she and former manager Jason Trawick were officially dating. Trawick co-starred in Spears’ music video for “Criminal” playing the hunky Clyde to her Bonnie. The couple became engaged last December—fingers crossed y’all!
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