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Who: Britney Spears and Justin Timberlake
Why: They were emblematic of the early 00s pop craze, becoming music’s prince and princess with simultaneously sky-rocketing careers. The fact that she was a self-proclaimed virgin only made their relationship more fascinating. Especially when rumors of infidelity turned out to be true and Justin dumped Britney for cheating on him.
Status: Split in 2002.