Why Did Britney Spears And Justin Timberlake Break Up?

Britney Spears and Justin Timberlake were basically the homecoming queen and king of the early 2000s. The two first met when they were just 11 years old. They had both been cast in the reboot of Disney's "The Mickey Mouse Club," and they worked together for a couple of years. "The Mouseketeers quickly split into our own cliques, divided by the dressing rooms that we shared: Christina Aguilera and I were the younger kids, and we shared a dressing room," Spears writes in her memoir, "The Woman in Me," adding, "I quickly connected with a boy named Justin Timberlake," according to People.

A friendship would blossom into a full-blown relationship less than a decade later, and Spears and Timberlake made headlines day in and day out. When they were first starting out in their respective careers — Spears as a solo artist and Timberlake as a member of the boy band NSYNC — they were also challenged with figuring out how to navigate their young love. Although many fans were convinced these two were endgame, the end came far sooner than anyone saw coming. In the years since, there has been plenty of speculation about why Spears and Timberlake's love didn't last, but thanks to her memoir, we have a much better idea of what really happened between her and Timberlake. 

One of the main reasons that Britney Spears and Justin Timberlake's relationship didn't work out is because they got together when they were super young. In fact, the two shared their very first kiss during a classic game of Truth or Dare. "Someone dared Justin to kiss me. A Janet Jackson song was playing in the background as he leaned in and kissed me," Spears wrote in her book, according to People. From there, it was like a whirlwind — two teenagers were embarking on careers in the entertainment industry, all while trying to figure out their futures together. By age 19, Spears and Timberlake were living together. 

In a 2001 interview with The Guardian, Spears talked about living on her own and was excited to show off her house. The outlet also reported that Timberlake lived with Spears whenever he wasn't touring the world with NSYNC. "I'm not ashamed at all to say that I love him from the bottom of my heart. As far as love is concerned, with him, too much is not enough. He's everything," she told the outlet at the time. 

But even Spears herself has acknowledged that the two didn't last because young love usually doesn't. "We're not perfect. I don't judge anybody. It's just young love. It's just young love. It was a very intense relationship, that's for sure," she told Barbara Walters in an interview on 20/20 that aired in 2002.

You could call Britney Spears and Justin Timberlake high school sweethearts, even though their versions of high school looked way different than anything a normie could imagine. While most 17-year-olds are busy running to their lockers to trade out textbooks before algebra, Spears and Timberlake were on tour buses, performing in front of thousands of screaming fans. Indeed, fame and fortune played a major role in the demise of this relationship — and both of them knew it. "We could literally go, 'Oh, man, let's go to Bali,' and we'd be on a plane to Bali. We were little kids with big toys. You do the math — that's not going to last," Timberlake told Vanity Fair in 2011.

Indeed, Spears and Timberlake couldn't just go to the mall like other kids their age. They'd need a full security detail, at the very least. While they may have been able to relate to one another on a level that not many couples can, the stress of the outside world proved to be too much and was another reason they split.

Justin Timberlake never outright said that Britney Spears cheated on him, but he let his song "Cry Me a River" do the talking for him. The music video for the hit single features a Spears look-alike who, uh, cheats on him. "He got what he wanted. I think it looks like such a desperate attempt, personally. But that was a great way to sell the record. He's smart. Smart guy," Spears told Rolling Stone in 2011. For years, fans theorized that Spears had some kind of affair with choreographer Wade Robson. And, in 2023, she confirmed it. 

"We were out one night and we went to a Spanish bar. We danced and danced. I made out with him that night," Spears wrote in her memoir (via The U.S. Sun). Interestingly, however, she says that she told Timberlake about it, and the two did not split up right away. The timeline isn't too clear, but when Timberlake did decide to end things, Spears said he did it via text message. "I was comatose in Louisiana, and he was happily running around Hollywood," she explained of the aftermath of the split, according to The New York Times.

For years, fans have been led to believe that Britney Spears cheated on Justin Timberlake, and that's why they broke up. However, Spears has revealed that she's not the only one who stepped out on the relationship. In an excerpt from the book, Spears claims that Timberlake cheated on her with another celebrity, though she didn't name the person, TMZ reported. Spears said that the woman is now married and has a family, so she chose to keep the name private so as to not stir up any issues. Of course, this has left the internet to fend for itself, and there is already a great deal of speculation surrounding who this woman might be. The going theory seems to be All Saints singer Nicole Appleton, thanks to an old newspaper headline that was posted on Twitter in 2019.

"She and Justin kept their eyes down as they were driven together from London's Mayfair club to the swanky St. Martin's Lane Hotel," the text in the paper read. Indeed, Timberlake was dating Spears at the time the photos were snapped. 

Britney Spears truly believed that she and Justin Timberlake were going to get married — and she was totally ready for it. "I really thought that I was gonna be with him [for] the rest of my life. I did," Spears told ABC News in 2003. She may have been very young at the time, but Spears would have started a family with Timberlake without question — and she's confirmed that on the inside pages of her memoir. In one of the biggest bombshells to come out of the book, Spears says that she actually got pregnant while she and Timberlake were together. However, he didn't want to have a child so young and ultimately convinced Spears to terminate the pregnancy. 

"It was a surprise, but for me, it wasn't a tragedy. I loved Justin so much. I always expected us to have a family together one day," Spears wrote. "If it had been left up to me alone, I never would have done it. And yet Justin was so sure that he didn't want to be a father. To this day, it's one of the most agonizing things I have ever experienced in my life," she added. Spears eventually ended up starting a family, welcoming her first of two sons with now-ex-husband Kevin Federline just three years after her 2002 split from Timberlake. 

In 2003, Britney Spears told Rolling Stone that Justin Timberlake actually tried to get back together with her after their split. "He called me up and asked me if it was OK. I can't believe I'm telling you this right now. But who cares. He called me up and wanted to supposedly get back together or whatever, but behind it was, 'And by the way, you're in a video that's coming out,'" she recalled. Spears was referring to Timberlake's video for "Cry Me a River." Spears said that the record label did give her an option to basically veto Timberlake's decision to feature an actor who was clearly her doppelgänger, but she let him roll with it.

It's unclear why Timberlake attempted to get back with Spears, but she clearly implied that it was a move to promote his new music video. What better way to get his new single to take off than to step out with the woman who broke his heart? But she didn't fall for it. Not only did Spears not take Timberlake back, but the two grew further and further apart as the years went by. "We haven't spoken in 9 or 10 years," he told Vanity Fair in 2011.

Britney Spears and Justin Timberlake may have loved each other, but as they got older, they changed as people, and their desires also seemed to change. Ultimately, their young love couldn't survive in a world filled with temptation, and they ended up on two very different paths. Timberlake expressed this quite clearly when discussing the relationship in another interview with Vanity Fair in 2011. "We were two birds of the feather — small-town kids, doing the same thing. But then you become adults and the way you were as kids doesn't make any sense. I won't speak on her, but at least for me, I was a totally different person. I just don't think we were normal; there was nothing normal about our existence," Timberlake said.

Timberlake would go on to marry actor Jessica Biel in 2012, and he eventually became a father, welcoming son Silas in 2015 and son Phineas in 2021. Spears' relationship history is a bit more complicated since her split from Timberlake; she's been married three times. In 2023, her marriage to Hesam "Sam" Asghari ended in divorce. "As everyone knows, Hesam and I are no longer together ... 6 years is a long time to be with someone so, I'm a little shocked but ... I'm not here to explain why because its honestly nobody's business," Spears wrote on Instagram in August 2023.