11 Men Who Were Lucky Enough to Date Britney Spears

After meeting on the set of The Mickey Mouse Club as kids, Britney and Justin began dating in 1999, though they didn't go public with their romance until a year later. Sadly, the two parted ways in 2002 following rumors that Britney cheated on him with choreographer and frequent collaborator Wade Robson.

Shortly after her split from Justin, Britney moved on with her dance choreographer, though several sources claimed that the two had been hooking up when she was still dating Justin. Britney and Wade carried on a relationship for about a year before eventually calling it quits in 2002.

In 2003, Britney had a brief fling with the former Hollywood bad boy. The stars only went out on one date, and Colin said he was "just a 26-year-old guy who's single and having a good time."

While Britney denies ever having a relationship with the Limp Bizkit singer, Fred reportedly dated Britney in 2003. During that time, Fred gushed about their romance on his band's website, saying that he had "never felt this way." However, Britney told Glamour UK that the relationship was one-sided, adding, "He's said some pretty amazing things about me, but, um, I think he leaped in too deep, too quick." In 2009, Fred opened up about their rumored romance once again, telling MTV News, "It just became a fiasco of madness . . . [But] I always stay true to my heart and true to everything I did and my intentions, and I am in no way a liar."

The "Gimme More" singer wed her high school boyfriend at the Little White Wedding Chapel in Las Vegas in 2004, but the marriage was annulled after just 55 hours.

Six months after annulling her marriage to Jason, Britney moved on with her backup dancer, who was still married to actress Shar Jackson at the time. After dating for a few months in 2004, the duo tied the knot in a surprise unofficial ceremony — they didn't have a prenup agreement, so it wasn't official for three weeks. The pair welcomed two sons together, Jayden James and Sean Preston, and even went on to have their own reality show on UPN called Britney and Kevin: Chaotic. However, as Britney's career took a turn for the worse, the two ended up pulling the plug on their marriage and split in October 2006, though their divorce wasn't finalized until July 2007.

While in the middle of her public meltdown in 2007, Britney shocked fans when she began dating photographer Adnan Ghalib. Their relationship only lasted a year, and officially ended when Britney filed a restraining order against him, claiming he was conspiring to take control of her affairs. In 2012, Adnan testified in a trial between Britney's former manager, Sam Lutfi, and her family, claiming Britney's mother once tried to coerce him, saying, "She requested that I say [to the media] Sam Lutfi was responsible for Britney Spears's behavior." The photographer also admitted that a judge ordered him to stay away from the singer for three years.

Britney started dating her former manager in early 2009, and the two got engaged in December 2011. The singer confirmed the news with a special tweet, writing, "OMG. Last night Jason surprised me with the one gift I've been waiting for. Can't wait to show you! SO SO SO excited!" Sadly, they never made it down the aisle and instead broke up in January 2013. Britney issued a statement, saying, "Jason and I have decided to call off our engagement. I'll always adore him and we will remain great friends."

Months after her split from Jason, Britney was photographed with a new man, who was later identified as David Lucado. David was a normal guy from the South, and the two dated for over a year in 2013. Britney seemingly confirmed their breakup in August 2014 when she tweeted out a cryptic status that read, "Ahhhh the single life!"

In 2014, the mother of two began dating Charlie, a TV producer from a Hollywood family. Britney confirmed the romance by sharing adorable photos of the two on Instagram and making their red carpet debut at the Billboard Music Awards, but alas, their relationship came to an end just eight months later.

Britney first met the dancer on the set of her "Slumber Party" music video in 2016. While it's unclear when these two officially started dating, the couple seemingly confirmed their romance in November 2016 when Sam posted an Instagram photo of him and Britney enjoying a romantic sushi dinner. Since then, Sam and Britney have shared a handful of cute moments together, including a fashion show date in LA and a stylish night out at a pre-Grammys party.