Britney Spears Reportedly Reached Out To Her Famous Ex Before Marrying Kevin Federline

Since the moment pop singer Britney Spears dazzled millions with "...Baby One More Time" in 1998, her love life has been a constant source of speculation. During the height of her popularity, Spears' match-in-pop-heaven relationship with Justin Timberlake only boosted her celebrity. Spears and Timberlake dated from 1999-2002, posing in matching denim outfits and gushing about each other in interviews before Timberlake ended the relationship in a text message, as Spears alleged in her 2023 memoir, "The Woman in Me." Spears' split from Timberlake hurt her more than we know — so much so that she actually reached out to Timberlake the night before her wedding to ex-husband Kevin Federline to say her "final piece," as Federline told Entertainment Tonight.

In September 2004, two years after Spears' split from Timberlake and on the eve of her wedding to Federline, the former backup dancer claimed that she called Timberlake to hash things out and put that chapter of her life behind her. "I couldn't imagine what it was like to be her, I couldn't imagine what it was like to be Justin in those moments, because they were super young," Federline told ET. "You're talking teenagers that had to go through this globally, and I know that they really cared about each other back then." Even as she was prepared to walk down the aisle with him the following day, Federline believes Spears was still "not over" Timberlake.

Britney Spears and Justin Timberlake split in 2002, and the rumor mill ran wild with theories that Spears cheated on Timberlake. In her memoir, Spears admitted that, while she did cheat on Timberlake with choreographer Wade Robson, she did so in retaliation after hearing rumors that Timberlake cheated on her, as reported by Vanity Fair. Timberlake's ego was clearly hurt after his breakup with Spears and in "Cry Me a River," a song on his 2002 album, he called out his former flame for betraying him, and taking his love for granted. For her part, Spears said that, post-breakup, she was "comatose in Louisiana, and he was happily running around Hollywood," in her memoir.

To better understand the full picture of their romantic chaos, you'll need to examine the full timeline of Spears and Timberlake's complicated relationship. In 2021, after Spears' conservatorship made headlines, the pair seemed to be on much better terms, with Timberlake taking to social media to voice his support for Spears. "Regardless of our past, good and bad, and no matter how long ago it was ... what's happening to her is just not right," Timberlake wrote on X. However, two years later, after sharing intimate details of their relationship in her memoir, including that she had an abortion because Timberlake "definitely wasn't happy about the pregnancy," tensions between the pair escalated again. Timberlake used live performances of "Cry Me a River" to throw subtle shade her way, according to Us Weekly, and Spears responded by making fun of his basketball skills. Let's just say it's been one wild ride for Spears and Timberlake (and we have no idea if it's over yet).