Britney Spears' Split From Justin Timberlake Hurt Her More Than We Know

Justin Timberlake and Britney Spears' romance began in 1999, leading to them becoming one of pop's biggest couples. Their parting in March 2002 was just as widely publicized. Breakup rumors had been swirling in the weeks leading up to their announcement. Spears had stopped wearing a promise ring given to her by Timberlake, and during a press run for her film," Crossroads," she admitted that the three-year relationship was over. While Timberlake acknowledged he was heartbroken over things ending, Spears may have been more hurt than we knew.

Timberlake's actions after the split seemed to disparage his ex. In his video for his first solo single, "Cry Me a River," he included a Spears lookalike. At the time, it appeared that Timberlake might have been trying to make the "Oops ... I Did It Again" star look like the bad person who caused their turmoil. During a November 2003 interview, Spears pushed back against this, telling Diane Sawyer, "I'm not technically saying he's wrong, but I'm not technically saying he's right either. It was a really weird time ... I just felt exploited and weird." While Spears put on a brave face, being dumped by Timberlake may have taken a lasting emotional toll.

Before Britney Spears suffered a mental health crisis that led to her almost 14-year conservatorship, her breakup with Justin Timberlake may have sparked an earlier breakdown. One source told Us Weekly that the tumultuous split was a "turning point for her mental issues," adding that Spears believed the pair would ultimately start a family one day. "So when he broke up with her, it shook her world," the source claims, noting "things shifted with her, and she started having problems."

Some of what the source claimed was substantiated by Spears herself in her October 2023 memoir, "The Woman in Me." In the book, she revealed how she had an abortion while dating Timberlake, who did not want to be a father, though she wanted the baby, writing, "I never would have done it. And yet Justin was so sure that he didn't want to be a father" (via Reuters). Spears admitted that this was one of the most painful points of her life, and the way he chose to end the relationship likely did not help things.

Britney Spears wrote in her tell-all that the relationship breakdown began as Justin Timberlake was working on his solo project, "Justified." This may have been due to Spears allegedly being the subject of many of the album's solo tracks. Timberlake broke up with the Grammy Award winner through text message. Making matters worse, Spears was on the set of her video, "Overprotected," when she received the notification that her relationship was over, allowing her little time to mourn. This left Spears hurt for years to come.

"When I say, devastated, I mean, I could barely speak for months. Whenever anyone asked me about him, all I can do is cry. I don't know if I was clinically in shock, but it felt that way," Spears wrote in her bestselling book, adding "It almost felt like I was suffocating, like I couldn't breathe after all that happened," (via Billboard). Unfortunately, this feeling still seemed to linger. After she offered a January 2024 apology on social media for many of the revelations in her book, Timberlake seemingly took a dig at Spears during his February 2024 New York City show, telling his crowd he'd wanted to "Take this opportunity to apologize — to absolutely f—ing nobody," [via NBC News]. According to an insider who spoke with Us Weekly in March 2024, these comments only triggered Spears, a dismal reminder that she may never quite get over the heartache of their separation.