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

Manifestation works in wonderful ways. Dating (or even marrying) your celebrity crush seems like something you only see in movies, but it happens in real life, too. And, coincidentally, it also happens to actual celebrities.

Way before they became Mr. and Mrs. Bieber, Hailey Bieber (née Baldwin) was merely a Belieber just like the rest of us. Hailey and Justin Bieber's first-ever meeting was even documented on "Today," as the Rhode founder could be seen meeting the pop sensation. Hailey even famously tweeted that she found Justin and then-girlfriend Selena Gomez to be perfect for one another. "I don't care what anyone says but Justin Bieber and Selena Gomez together is the definition of a teenage dream!" she penned. Meanwhile, David Beckham, who was only an up-and-coming football star before he met his wife, Victoria, already harbored a huge crush on the "posh" Spice Girl. "That one there, that's the girl I'm going to marry," he told a friend after watching a Spice Girls music video.

Manifestation apparently worked for Justin Timberlake, too. Growing up, he had a massive crush on actor Alyssa Milano, but never in his wildest dreams did he imagine that they would eventually date.

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!"

While Alyssa Milano and Justin Timberlake's romance only lasted a few months, it apparently had a big impact on Britney Spears. In 2013, the "Charmed" star proudly admitted to Access Hollywood that she was Timberlake's first fling right after he dumped Spears. "Yeah that's true," she said when asked if they really dated. "That was right after Britney broke his heart, I swooped in for the kill!"

Then, in 2022, when Spears was exhibiting erratic behavior on social media, Milano took to Twitter to express her concern. "Someone please go check on Britney Spears," she wrote. But, Spears took it the wrong way, and thought the actor was "bullying" her. According to a source, Spears' frustration stemmed from her lingering feelings for her ex. "Britney was genuinely upset by Justin and Alyssa. When they ended up dating right after their split, it confirmed her fears. Out of all her fixations with the past, this is the one that's bugging her right now — and it's caused some trouble with Sam [Asghari]," they told Closer. "The fact she brought up Alyssa's old Tweet makes him wonder how fixated she still is with Justin."

Not one to escalate things further, TMZ reported that Milano made the effort to reach out to Spears to apologize, but it's unclear if the "Toxic" singer accepted it.