Britney Spears's Relationships

She’s got a successful career, a whole lotta crazy and a storied dating rolodex to match. Britney Spears first exploded on the scene as an innocent 16-year-old dancing around in a Catholic schoolgirl uniform, but it wasn’t long before we all knew that she shouldn’t be wearing white to her wedding (both of them). But she even warned us herself—she’s not that innocent.
As a young teen star, the very religious Brit revealed that she would be staying a virgin until marriage. At the time, she was in a serious relationship with her Mickey Mouse Club co-star and fellow pop phenomenon, Justin Timberlake, but their contact was probably limited to some necking and over-the-clothing touching.
The pair shared a starry-eyed, all-smiles romance from 1998 to 2002 when they suddenly broke up and the claws came out. There were rumors that Spears cheated on Timberlake with choreographer Wade Robson, and Timberlake had no qualms about airing their dirty laundry. In two songs, “Never Again” and “Cry Me a River,” clearly directed at his ex, he laid the blame for their split squarely on Britney. Even more sensational was when he cast a Britney look-alike in his video for “Cry Me a River” in which he gets revenge on a cheating ex by filming a video of himself getting freaky with someone else.

Britney never commented on the allegations, but she released a song of her own, “Everytime,” an apology song that sounded like it was directed to Timberlake. But that didn’t stop him from appearing on 20/20 later that year and revealing that Spears wasn’t a virgin. She responded in W magazine several months later saying, “It was two years into my relationship with Justin. And I thought he was the one. But I was wrong. I didn’t think he was gonna go on Barbara Walters and sell me out.”
Oddly, in the history of Britney Spears, her romance with Timberlake was the most functional and drama-free. Following their split she reportedly had flings with Fred Durst, Colin Farrell and Jared Leto before she suddenly eloped with her childhood friend Jason Alexander in Las Vegas on January 3, 2004. The wedding was annulled 55 hours later.  

That same year, she met backup dancer Kevin Federline. Three months later they were engaged, and on September 18, 2004, they were married. During their two years playing house, Britney gave birth to two sons, Sean Preston and Jayden James. The messy divorce and ensuing custody battle paved the way for her much-publicized mental breakdown, during which she had paparazzi staking out her house at all times. Inexplicably, she began to date one of the creepy photographers who was making a living stalking her. The short-lived romance with Adnan Ghalib ended when her father took conservatorship of her and got a restraining order against him.

Britney, under the watchful eye of her father, stayed single for a year before starting a relationship with her then-agent Jason Trawick in early 2009. Trawick, a close friend of her older brother, Bryan, received the stamp of approval from her family, and the two have been together since. Still no signs of a tell-all book or Dateline interview, but in the romantic world of Britney, you never know.
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