Britney Spears: A Boyfriend (and Husband) Restrospective

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Britney Spears is dating her agent, Jason Trawick.

With fans of the singer almost universally lauding her new relationship with this slightly older, solid individual, questions of whether he is "the one" have already popped up. Of course, this is not the first time a man has been in this position.

Far from it.

Below, The Hollywood Gossip reflects on the men in Britney's life. As was the case with our recent Paris Hilton boyfriend retrospective, the list is not short.

1996: Reg Jones. Britney's first boyfriend is alleged to have nabbed her virginity when she was just 14. This explains so much regarding l'il Jamie Lynn.

1999-2002: Justin Timberlake. For a time Britney and Justin were the first couple of crappy, mass-produced pop music. Then she cheated on him with Wade Robson and went downhill, while he became a true music star in his solo career.


2002: Fred Durst. The Limp Bizkit frontman got it on with Spears after her breakup with JT, forever damaging any credibility he once had as a rock musician, but probably gathering some amazing material to brag about to friends at bars.

Best. Kiss. Ever.

2003: Madonna. Okay, sorry, there was no actual relationship between Madonna and Britney Spears. But c'mon, one of the best Britney Spears pics and hottest moments in girl-on-girl action history has to count for something. Right? Right.

Britney Spears, Jason Alexander: Party Time

2004: Jason Alexander. Sure, they were only married for 55 hours until she had that $h!t annulled. But think about it, he must have gotten lucky at least once. They got wasted and married in Vegas! Who actually does that?

A Pregnant Britney Spears

2004-2006: Kevin Federline. For about two years, Kevin Federline made an honest woman out of Britney Spears. They had two children, Sean Preston and Jayden James, just the cutest things ever. At some point, though, she realized that she was Britney Spears, and that she was married to Kevin Federline.

2006: J.R. Rotem. He tapped that wheelbarrow style. Enough said.

2007: Isaac Cohen. Isaac and Britney really seemed like they had a good thing going, and they did, until she went bat$h!t crazy and they broke up. Issac later cashed in, giving a classic interview about their marathon boink sessions.

2007: Jason Filyaw. This random rocker developed a relationship with the singer, even going so far as to say he was in love with her on MySpace, then went AWOL.

2007: Howie Day. The lame excuse for a singer followed in Filyaw's footsteps, but things went south when she OD'd. A rehab romance is doomed from the start.

2007: Daimon Shippen. Britney and oafish bodyguard Daimon dated briefly during her prime meltdown days. He fell off the face of the Earth almost immediately.

Brit Brit

2007-2008: Adnan Ghalib. This shady fella had been working as a paparazzo, taking photographs of Spears outside her house, when one night she invited him into her car and began a sexual relationship with him, natch.

2009: Chase Benz. Britney was romantically linked to Chase, one of her Circus tour backup dancers, earlier this year. More than likely, though, they simply danced suggestively during her traveling S&M show and people got the wrong idea.

2009: Jason Trawick. Finally, a stable guy. One that Jamie Spears knows and approves of. We imagine they'll get married someday for that reason alone.

What do you think? Is Jason Trawick the one? Should Britney marry him?

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Britney Spears Biography

Check Please!
Wow. Britney Spears is ... just.... OMG. Wow. Just wow. With this girl, that's about all we can say at this point. Once the biggest... More »
Kentwood, Louisiana
Full Name
Britney Jean Spears

Britney Spears Quotes

I miss it here so much! I love it so much! It makes me it's kinda like bittersweet coming here because I used to live here for two years. And when I come here, it's like, man, I wish I had my apartment here still.

Britney Spears [on New York City]

MTV has long played an important role in my career. How can I not be there to kick off their 25th VMAs?

Britney Spears