Throughout the years, Britney Spears has had more than a few relationships, one-night stands and flings. Her love life has more twists and turns than a soap opera, and we’re here to break it all down for you. Here are all the juicy details on the guys Britney has been with.
1. Wade Robson was hired as Brit’s choreographer, and the two hooked up for a few months. This wouldn’t have been such a big deal if Brit wasn’t dating Justin Timberlake at the time. Awkward!
2. When Brit entered a Malibu, California rehabilitation facility in February 2007, she found more than just some help on how to kick her drug and alcohol addictions. The singer met
recovering addict and singer Howie Day at the facility, and the two dated briefly before going their separate ways.
3. In 2004, Brit and a childhood friend named Jason Alexander jetted off to Las Vegas, partied, got wasted, and randomly got married. As soon she shared the news with her family and
managers, they reportedly “freaked out” because Brit and Jason didn’t have a prenup. Brit was quickly convinced to end things, and the marriage was annulled 55 hours later.
4. The pop star and magician Criss Angel dated briefly in 2007 right before Brit’s comeback MTV VMA performance. Criss was supposed to perform alongside her at the awards show, but the singer left him high and dry and decided to do the show without him.
5. TV personality Mario Lopez had a one-night stand with Britney in Las Vegas, and he
confirmed all the juicy details in his memoir. I guess what happens in Vegas, doesn’t really stay there after all.
6. Record producer J.R. Rotem had a brief fling with Britney while she was still legally married to Kevin Federline, and he said Britney’s favorite position was “the wheelbarrow.” Their relation-ship ended when they both mutually agreed to keep their relationship on a business level.
7. Although her record company marketed her as a sweet and innocent virgin, Brit actually lost her virginity to her very first boyfriend, Reg Jones, back in 1995.
8. David Lucado and Britney dated for almost two years, and everything appeared to be going well up until the singer discovered a video of David making out with another woman. After their split, Britney confirmed the breakup on Twitter by tweeting out, “Ahhh the single life!”
9. Since the paparazzi was spending most of their time chasing her all around town, Brit
decided to make one of the photographers her boyfriend. She began dating paparazzo Adnan Ghalib in 2008 and quickly moved him into her house. They later broke up, and the singer was forced to get a restraining order against him.
10. When Brit posted a throwback photo of herself and Leonardo DiCaprio, the Internet went wild. According to sources, the two have been friends for years, and Leo has always had a
major crush on her. Is it possible they’ve hooked up? We think so.
11. Brit and rockstar Fred Durst dated in 2002, and he defended their love by saying, “Anybody out there who has a serious problem with my feelings for Britney should just chill.”
12. Britney was rumored to be dating musician and actor Jared Leto back in 2003. Even though Jared denied the rumors, the two were photographed out on the town together.
13. After ending her marriage to Kevin Federline, Brit began dating Isaac Cohen. The two
enjoyed a passionate love life, but Isaac said Brit was emotionally unstable, and she would roll up into a ball and cry after they were intimate.
14. Dating Colin Farrell is like a right of passage for Hollywood stars, and Brit had her turn with the Irish bad boy in 2002. They even showed up on the red carpet together for the premiere of his film, “The Recruit.”
15. In 1999, Britney went on tour with a group called Boyz-N-Girlz United and began dating one of its members, Robbie Carrico. Robbie even accompanied Brit to the world premiere of her music video for “Drive Me Crazy.”
16. Columbus Short choreographed one of Brit’s shows back in 2003, and the two had a brief fling. Columbus was married at the time, and he claims hooking up with Brit was one of the
reasons his marriage came to an end.
17. Britney met Sam Asghari on the set of her music video “Slumber Party,” and the two
immediately hit it off. Sam later posted a photo of himself and the superstar getting cozy on a sushi date.
18. When Jason Trawick proposed to Britney in 2011, everyone thought the singer had finally found her happily ever after. Unfortunately, the relationship didn’t last, and they ended their
engagement in 2013.
19. After three months of dating, Britney and Keven Federline got married. They later had two children together, but their marriage came to an end in 2007. Their divorce and the threat of
losing custody of her sons is said to be what triggered her infamous meltdown when she shaved her head and vandalized a photographer’s car with an umbrella.
20. Brit and Justin Timberlake seemed to have the perfect young romance.