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20 Guys Britney Spears Has Dated

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Two decades of tabloid headlines, one very public love life.

Britney Spears has spent more time under the paparazzi lens than almost anyone in pop music, and that includes every boyfriend, fling and 55-hour husband along the way. TheThings Celebrity’s rundown, 20 Guys Britney Spears Has Dated, traces her romantic history from her Kentwood, Louisiana high school days through the fall of 2016, when she was photographed for the first time with a new man on the set of her “Slumber Party” video. The list runs from hometown sweethearts to Grammy winners to a paparazzo who somehow talked his way into her inner circle.

• Spears dated hometown boyfriend Reg Jones starting in 1994, before she left for New York to chase a recording contract.
• Her relationship with Justin Timberlake ran from 1998 to 2002 and became the most scrutinized celebrity breakup of that era.
• Her marriage to childhood friend Jason Alexander in Las Vegas in January 2004 lasted just 55 hours before it was annulled.

The Justin Timberlake Years

Before Britney was even out of her teens, she was dating her *Mickey Mouse Club* co-star Justin Timberlake, a relationship that ran from 1998 until their split in 2002. The pair were pop music’s reigning couple during that stretch, and their breakup generated the kind of coverage usually reserved for actual celebrities getting divorced, not two 20-somethings calling it quits. The fallout from that split has been revisited by her own family members over the years, including in comments Jamie Lynn Spears has made about her sister and Timberlake long after the two moved on.

In the years right after Timberlake, Britney was linked to choreographer Wade Robson and spotted with actor Colin Farrell, who brought her to the 2003 premiere of his film “The Recruit.” Neither relationship was ever confirmed as anything more than a fling, but both kept the tabloids busy while she was recording and promoting new material.

Fred Durst, Columbus Short, and a Very Public Denial

Fred Durst, frontman of Limp Bizkit, publicly claimed in 2003 that he and Spears were romantically involved while the two worked together on tracks for her album “In the Zone.” Spears denied it outright, but Durst’s comments made headlines regardless, feeding a narrative about her love life that she rarely got to control.

Durst said he and Spears were an item while cutting tracks for “In the Zone.” Spears said otherwise.

That same year, Spears was briefly linked to backup dancer Columbus Short. It was a short fling by all accounts, one of several 2003-era relationships that came and went while she was juggling album promotion and constant media attention.

The Vegas Marriage and Kevin Federline

Nothing on the list tops the sheer speed of what happened in January 2004: Spears married childhood friend Jason Alexander in Las Vegas, and the marriage was annulled just 55 hours later. It remains one of the shortest celebrity marriages on record.

Later that same year, Spears married dancer Kevin Federline. The couple had two sons together, Sean Preston and Jayden James, before divorcing in 2006. It was, by far, the longest and most consequential relationship on the list, producing the children who have remained a constant in her life ever since.

Ghalib, Trawick, and the Road to Sam Asghari

Following her divorce from Federline, Spears was linked to paparazzo Adnan Ghalib between 2007 and 2008, a relationship that drew criticism given his profession. She then dated her own talent agent, Jason Trawick, starting in 2009. The two got engaged in December 2011 before mutually calling off the engagement in early 2013.

From there, Spears dated legal researcher David Lucado and producer Charlie Ebersol before meeting model and fitness trainer Sam Asghari on the set of her “Slumber Party” music video in late 2016. Their history-of-relationships pattern isn’t unusual for a star of her profile — Megan Fox’s own relationship history follows a similarly public arc of high-profile romances playing out in real time.

Asghari and Spears met on that “Slumber Party” set just months before this rundown was published, which puts him at the very end of a list that started with a Kentwood high school boyfriend back in 1994. Twenty-two years, twenty guys, and the cameras never once looked away.