19 Boyfriends of Britney Spears

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Britney Spears has dated some interesting characters over her many, many years in the spotlight. Here's a quick rundown!

1. Reg Jones

Reg Jones
Yes, the man who took Britney's v-card was a high school love named Reg Jones.

2. Jason Geddert

Jason Geddert
Jason Geddert (photo not available) is said to be one of her first loves. We can't believe he was never documented on photo or film either.

3. Justin Timberlake

Justin Timberlake
These two were the prince and princess of pop for a time. Until, of course, she cheated on him with ...

4. Wade Robson

Wade Robson
Choreographer Wade Robson, the other man immortalized as "him" in "Cry Me a River," JT's 2002 breakup anthem.

5. Tom Brady

Tom Brady
Before Bridget and Gisele, Tom Brady and Britney actually went on a few dates in 2002. Seriously.

6. Fred Durst

Fred Durst
Britney was linked to Limp Bizkit "singer" Fred Durst in 2002-03 ... along with unconfirmed flings Jared Leto and Colin Farrell. It was an interesting time for her.

Wait! There's more Boyfriends of Britney Spears! Just click "Next" below:

Bruce schnelle

She has had more sex with different guys than carter has liver pills...

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@ Bruce

Whatever

Bruce schnelle
@ elle_b_sure

Sounds like your ok with that...

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Britney Spears Biography

Britney Spears: Harper's Bazaar Style
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 »
Born
Birthplace
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