Britney Spears has had her share of breakups and makeups.
From her first love Justin Timberlake to her first husband Jason Alexander, most of her relationships, unfortunately, played out in front of the world.
Here are some of her most high-profile and controversial courtships to date…
Spears and Justin Timberlake were pop’s golden couple when they started dating in 1998. She was the biggest pop star at the time and he was the breakout star of boy band *NSYNC.
After gifting fans with memorable (and sadly unforgettable) moments like matching denim outfits to the American Music Awards in 2001, the duo parted in 2002 after four years together.
Their breakup was far from scandal-free, with rumours Spears cheated on him with choreographer Wade Robson. Timberlake did little to shut down the speculation, sparking more rumours when he released his single ‘Cry Me a River’ in 2002, which featured a Spears lookalike in the music video who cheats on him.
The rumours Spears and dancer-choreographer Wade Robson just wouldn’t go away.
It’s believed the pair hooked up in the early 2000s around the time of her ‘(You Drive Me) Crazy’ music video, which featured Wade.
It was suggested that her boyfriend at the time, Timberlake, found a note from the dancer to Spears in her Saturday Night Live dressing room back in 2002, which lead to their breakup.
The rumours have never been confirmed.
In 2003, Spears shocked fans when she walked the red carpet with Hollywood bad-boy Colin Farrell at the premiere of his movie The Recruit. Apparently, the pair met when he was filming another cop thriller S.W.A.T. and for 12 full days, they appeared to be an item.
Despite Spears infamously rocking a slogan tee that read, “I slept with Colin Farrell and all I got was this lousy T-shirt”, the pair insist they were just friends. Side note: it was the actor who reportedly sent the T-shirt to Spears as a gift.
Farrell later claimed it was all just rumours, telling Entertainment Tonight, “She’s just a mate. Seriously, we just met a week ago, [we’re] having a laugh.”
Backup dancer and now actor Columbus Short only recently confirmed rumours he and Spears had a brief fling back in 2003.
“[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.”
In 2004, Spears married her childhood friend Jason Alexander after a wild few days in Las Vegas. They were both 22 years old at the time.
The bride wore ripped jeans and the groom a baseball cap for the quickie ceremony inside A Little White Wedding Chapel in Sin City.
Needless to say, Spears’ people were livid and had the wedding annulled just 55 hours later, arguing the pop star “lacked understanding of her actions, to the extent that she was incapable of agreeing to the marriage”.
Meanwhile, Alexander told Access Hollywood at the time, “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.”‘
Just six months after her annulment, Spears met backup dancer and father-of-two Kevin Federline at a nightclub in LA in July 2004.
They got engaged after two months of dating and then surprised family, friends and fans when they married weeks later.
“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.”
Their whirlwind romance continued and in 2005, they welcomed their first son, Sean Preston. One year later, they welcomed another son, Jayden James.
Only two months after giving birth to their second child, Spears filed for divorce from Federline, citing irreconcilable differences. Their divorce was finalised in 2007.
Spears concerned both her team and fans when she began dating photographer Adnan Ghalib in 2007 after her split from Federline. The couple were seen all around LA together, and Ghalib was often present during some concerning events that transpired in Spears’ life at the time.
When Spears’ conservatorship was established in 2008, her dad Jamie became conservator and he immediately slapped restraining orders on Ghalib and her then-manager Sam Lutfi.
In 2009, Spears began dating her then-agent Jason Trawick. At the time, he worked for William Morris Endeavor Entertainment, where she was a client, and he even became a co-conservator of her estate.
The couple went public with their romance when they walked the 2010 Grammy Awards together hand-in-hand, and 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, each releasing a 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.”
Trawick is no longer a co-conservator of Spears’ estate, and she has since moved on to a new talent agency.
Spears took a break from dating until 2016 when she met her current boyfriend Sam Asghari 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 didn’t call back until five months later 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.”
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