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.

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