Pitt's the one who lost his head for Paltrow on the set of 1995's Se7en. They were the mid-90s couple, from the top of her slip dress to the ends of his frosted tips. Accepting the Best Supporting Actor Golden Globe for 12 Monkeys in 1996, Brad thanked Gwyneth, his "angel, the love of my life," and he proposed that December. They even had matching haircuts at one point.

"I take the institution extremely seriously. There are no divorces in my family either—and in his either, so this is not something—we've been together for quite some time, so this is not a rash decision," Gwyneth convincingly told Entertainment Tonight about their engagement. But in June 1997, they broke up.

"When two people aren't supposed to be together, they're not supposed to be together," a defiant Paltrow said in 1998. Fast-forward to 2015, when she told Howard Stern, "I was such a kid, I was 22 when we met. It's taken me until 40 to get my head out of my ass. You can't make that decision when you're 22 years old... I wasn't ready, and he was too good for me."

Moreover, her dad, Bruce Paltrow, was "devastated" when they broke up. "My father loved him like a son." Ultimately, Paltrow said, "I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!"