20 Celebrity Couples You'll Never Guess Dated in Real Life

Justin Timberlake and Fergie

Dated: 1998

Though this relationship was so far pre-Jessica Biel that it was even before Britney, it still makes us scratch our heads. However, if you consider the point in their lives they started dating, it makes just a tad bit more sense. Timberlake was just gaining momentum as a teen superstar with NSYNC and Fergie was in her own bubble gum pop group, Wild Orchid.

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