Britney Spears Boyfriend: Everything we know about her Dating History

Itziar Morte

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Our very favourite Britney Spears is very famous for her share of breakups and makeups. From her first love Justin Timberlake to her first husband Jason Alexander and most of her relationships, unfortunately, played out in front of the world. If you are wondering about all of her relationships then here are some of her most high profile and controversial courtships or hookups until now.

Justin Timberlake

Britney Spears' dating history: Everything we know about her past and present relationships

One of Britney Spears first boyfriends was pop’s golden couple when they first started dating in 1998. She was also one of the biggest pop stars at the time and he was also the breakout star of boy band NSYNC.

After gifting the fans a bunch of memorable moments like matching the denim outfits to the American Music Awards in 2001. However, the duo parted ways in 2002 after four years of their relationship which came as a huge shocker for all the fans who admired them together. Although their breakup was scandal-free, there were rumours that Spears actually Cheatem Timberlake with choreographer Wade Robson.

Wade Robson

Britney Spears' dating history: Everything we know about her past and present relationships
Image: express.co.uk

The rumours of Spears and dancer-choreographer Wade Robson never faded away. It is also believed that the pair actually hooked up in the early 2000s around the time of her music video which featured Wade. It was also reported that his boyfriend at that time was Timberlake. He found both Wade and Spears together in Saturday Night Live dressing room back in 2002 that ultimately lead to their breakup.

Colin Farrell

Britney Spears' dating history: Everything we know about her past and present relationships
Image: evoke.ie

In 2003, Spears finally shocked fans when she walked the red carpet with the bad boy Colin Farell during the premiere of his movie The Recruit. The pair met when the filming of another cop thriller SWAT was on for 12 days they appeared altogether. The pair although they insisted that they were just friends but later reports claimed they were actually in a relationship but had a healthy break up because they did not want to spoil their friendship.

Columbus Short

Britney Spears' dating history: Everything we know about her past and present relationships
Image: cheatsheet.com

The famous backup dance and the current actor Columbus only recently confirmed that the rumours of He and Spears had a great fling back in the year 2003. He said: Britney was on me like white on rice, and would not leave me alone the entire night. Britney had her eyes on the prize and wasn’t about to stop until she got what she wanted,” the Stomp The Yard star wrote in his 2020 memoir Short Stories: The Autobiography of Columbus Short. “We ended up being intimate that one time. I never slept with her again after that, though.

Jason Alexander

Britney Spears' dating history: Everything we know about her past and present relationships
Image: instyle.com

In 2004, Spears got married to her childhood friend Jason Alexander after spending a few days in Las Vegas. They were just 22 years old during that time. The bride actually wore ripped jeans and the groom a baseball cap for a quick marriage ceremony inside a little white chapel in Sin City. Alexander also told Access Hollywood that “It was just crazy, man. And we were just looking at each other and said, ‘Let’s do something wild, crazy. Let’s go get married, just for the hell of it.”

Kevin Federline

Britney Spears' dating history: Everything we know about her past and present relationships
Image: nme.com

Just six months after her annulment Spears also met a backup dancer and father of two Kevin Federline at a nightclub in LA in July 2004. Both of them got engaged after just two months of dating and then surprised the whole family when they got married a few weeks later. He said in his statement:

“I met her at a club in Hollywood, Joseph’s. Our eyes met and that was it. We just hit it off right away,” Federline would later tell People. “I was madly in love with her. Everything just seemed so right. I didn’t see it as too fast or too slow.”

The very cute and whirlwind romance also continued and they welcomed their first son Sean Preston and just one year later they welcomed another son Jayden James. But just after giving birth to their second child in just two months, Spears filed for divorce from Federline due to irreconcilable differences. Finally, the divorce was finalized and they were separated in 2007.

Adnan Ghalib

Spears made a huge concern amongst her fans when she started stating the photographer Adnan Ghalib in 2007 after her split from husband Federline. The couple were first spotted around LA together. Ghalib was also present during some concerning events that also transpired in Spears life at that particular time.

Jason Trawick

Britney Spears' dating history: Everything we know about her past and present relationships
Image: eonline.com

In 2009, Spears again tried her luck at dating her then agent Jason Trawick. During that time he worked for William Morris Endeavor Entertainment, where she was a client and he became co-conservator of her estate. The couple went public with their romance when they walked in the 2010 Grammy Awards together hand in hand. In 2011 they announced their engagement at a party at Las Vegas Planet Hollywood Resort & Casino. But in 2013, the couple ended their four-year relationship and year-long engagement by releasing their statement of their own.

“I’ll always adore him and we will remain great friends,” the pop star wrote in hers, while Trawick said, “I love and cherish her and her boys and we will be close forever.”

Sam Asghari

Britney Spears' dating history: Everything we know about her past and present relationships
Image: hollywoodlife.com

Spears also took a break from dating until 2016 when she met her current boyfriend Sam Asghari which is on the set of her music video for Slumber Party. “We were waiting and waiting together for 20 minutes at a time, literally stuck there,” she explained in a radio interview the following year. “We were forced to talk to each other.”

Spears said he gave her his number but she did not call back until back five months when she found it stashed in her purse. “I kept his number, and it was so weird because it was like five months later that I found his number in my bag,” she shared. “I was like ‘He was really cute. This guy was really cute!’ so then I called him. He is just a really fun, funny person.”

So this was all about Britney Spears all boyfriends and her dating history. Let’s hope she finds someone who is the best for her.

 

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