Brad Pitt is known for his relationship with Gwyneth Paltrow, which began on the set of the 1995 film Se7en. They were the quintessential couple of the mid-90s, showcasing their style from her slip dress to his frosted tips. In 1996, while accepting the Best Supporting Actor Golden Globe for 12 Monkeys, Brad expressed his gratitude to Gwyneth, referring to her as his “angel, the love of my life,” and proposed that December. At one point, they even sported matching haircuts.

“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 stated confidently to Entertainment Tonight regarding their engagement. However, they ended their relationship in June 1997.

“When two people aren’t supposed to be together, they’re not supposed to be together,” Paltrow asserted in 1998. Fast-forward to 2015, when she shared with 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.”

Additionally, her father, Bruce Paltrow, was “devastated” by their breakup. “My father loved him like a son.” Ultimately, Paltrow reflected, “I definitely fell in love with him. He was so gorgeous and sweet. I mean, he was Brad Pitt!”