Then: 'N Sync's Justin Timberlake and Britney Spears were the Jay Z and Beyoncé of bubblegum pop when they posed for a snapshot with Charmed actress Alyssa Milano and her close friend Alaa Khaled. Milano shared the undated photo with a simple caption, "#TBT Justin, Britney, Alaa, and me!" However, since Justin and Britney appear to be very much together in it, the pic must have been taken before the tragic Spears-Timberlake breakup of 2002 — and before Milano briefly coupled up with Timberlake herself later the same year. At the time, Alyssa was 29 while Justin was only 21. Milano joked that, "After Britney broke his heart, I swooped in for the kill!"
Related: Celebrity Throwback Snaps
Now: Timberlake, along with both exes in this throwback, is now a parent. After dating Spears, Milano, Cameron Diaz, and others, he tied the knot with Jessica Biel. The couple welcomed their first child, a son named Silas, in April.