40 Celebrity Couples You Forgot Dated In The Early ’00s
Alyssa Milano and Justin Timberlake
Alyssa Milano and Justin Timberlake dated shortly after his breakup with Britney Spears. Was this before, after, or during Justin’s fling with Jenna Dewan? The world may never know. Alyssa seems like a cool girlfriend, gushing over Britney and JT’s true love to Entertainment Tonight in 2015, saying they “just seemed like the perfect match!” Alyssa and Justin dated for only a few months in the ’00s, and Alyssa is pretty blase about the whole thing. Alyssa wasn’t surprised when Justin and Britney broke up because they were only twenty, so her short-lived romance probably wasn’t all that surprising to the young star either.