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 afte

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