She formerly dated Justin Timberlake.

Britney and Justin were the legendary pop power couple from 1998 until 2002. The two were inseparable when their respective careers were at their peak. Spears and Justin Timberlake, her co-star from the Mickey Mouse Club, had already reconnected when she opened for NSYNC on a number of tour dates before the album's release. They soon started dating, and from 1998 to 2002, they were one of the most talked about couples of the time.

At the 2001 American Music Awards, the duo donned identical faded denim ensembles, which resulted in one of the most notorious images of that time period. However, it wasn't their first encounter with special attention. They donned matching jerseys with their monikers, "Pinky" for her and "Stinky" for him, emblazoned on them to a charity basketball game.

Their relationship was unexpectedly amicable, at least on the surface for a famous couple. Fans were therefore stunned to learn that Spears and Timberlake had split up in 2002. Soon enough, several rumors, some worse than others, began to circulate regarding the reason behind the breakup.

After that, in 2002, Justin Timberlake put out a new song called "Cry Me a River." His solo career began with the album's second single. There was a Britney lookalike in the music video for the song, which fueled allegations that she was being disloyal to him. In response, Britney created the ballad "Every time." Later that year, Fred Durst, the lead singer of Limp Bizkit, announced his relationship with Britney; however, she denied it.