Sometimes Hollywood is truly a small world, and if anything proves that, it’s today’s TBT picture Alyssa Milano shared. The photo that Milano shared is of her, Britney Spears, and Justin Timberlake.
What makes this epic TBT photo so awkward, you ask? Well, back then, Justin Timberlake and Britney Spears were still going strong. For those that aren’t aware, Justin and Britney were pop music’s King and Queen, and when they started dating, everyone went crazy. Those who followed their relationship religiously thought that they were the real deal.
Although they dated for three years (which, totally seemed like forever at the time), Britney Spears allegedly cheated on Justin Timberlake with mutual choreographer and friend Wade Robson. Back then, it was a scandalous split that resulted in Timberlake’s “Cry Me a River.” What some don’t know is that once Timberlake was single, the first relationship he dove into was with none other than Alyssa Milano.
Alyssa Milano, Justin Timberlake and Britney Spears oh my! http://t.co/scDwCisVSt pic.twitter.com/L8RYVSQs89
— ET Canada (@ETCanada) August 20, 2015
Milano didn’t comment on the awkwardness of the photo, but she told Access Hollywood back in 2013, “That was right after Britney broke his heart. I swooped in for the kill!”
Since then, all parties have moved on. Justin Timberlake went on to date Cameron Diaz and then Jessica Biel, who he married in 2012. The two welcomed a son, Silas Randall Timberlake, in April of 2015. Meanwhile, Alyssa Milano went on to date CAA agent David Bugliari. The two were married in August of 2009 and welcomed a son Milo, 4, and a daughter, Elizabella. As for Britney Spears, she moved on after Timberlake with ex-husband Kevin Federline, with whom she had two children, Sean Preston, 9, and Jayden, 8. The two went on to divorce, and since then, Spears has dated a string of guys, but nothing has stuck so far.
While Timberlake no longer talks about his past relationships, he opened up to Ellen DeGeneres about his wife, Jessica Biel.
At the time, he said, “Every once in a while I can catch a glimpse of her when she doesn’t see me looking, and I have this moment where I’m like, ‘If you only make bad decisions for the rest of your life, you made one really good decision.'”
He added, “It’s nice to marry your best friend. It suits me.”
Are you surprised to find out that Justin Timberlake dated both Britney Spears and Alyssa Milano?
[Photo by Alyssa Milano / Instagram]