Justin Timberlake Had A Poster Of Alyssa Milano Growing Up (& Then They Dated)

Pretty much everyone had a childhood crush or two growing up, and for Justin Timberlake, the girl of his dreams was Alyssa Milano. In an interview with Rove & Sam in 2016, he revealed that he was a big fan of the series "Who's the Boss?" when he was younger, which happened to star Milano. He dished that he had posters of her face on his walls back then — a fact that he revealed to her when they were romantically linked in 2002. "My big crush was Sam in 'Who's the Boss?,' Alyssa Milano," he recalled. "Then we dated briefly, so that got weird ... I was like, 'Hey, I used to be obsessed with you when I was a kid.'"

Their brief relationship was far from serious, though. Timberlake and Milano got together shortly after the "Cry Me A River" singer controversially split from Britney Spears. Speaking with Entertainment Tonight in 2015, Milano said that, at the time, she thought Timberlake and Spears were a "perfect match" even though she was involved with the NSYNC member. She added, "They were super cute, super in love!" but she never expected them to last. "They were 20!"

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