The Hollywood superstar may not have caught the public’s eye until starring as a cowboy hitchhiker in the 1991 film Thelma & Louise, but his handsome features and irresistible charm were already a staple in the industry dating pool long before then.

In 1984, Pitt was linked to British-American singer Sinitta, whom he dated off and on for two years. The “Love and Affection” singer later revealed during a stint on the U.K.’s I’m a Celebrity…Get Me Out of Here that the young Pitt was “beautiful with the most amazing body” and “very sweet” while they were together.

Following a series of brief relationships with costars from his guest appearances on TV shows like Dallas and Head of the Class, the Inglourious Basterds star popped the question to Cutting Class actress Jill Schoelen in 1989. Their engagement lasted only eight months before Schoelen reportedly found a new man while shooting a movie in Hungary.

Nearly 10 years later, Pitt was engaged once again — this time to Se7en costar Gwyneth Paltrow. The two were viewed as Hollywood’s next It Couple before calling it quits in 1997. In 2015, Paltrow opened up to Howard Stern about the “devastating” end of her relationship with Pitt. “I was such a kid,” the Politician star said at the time. “I wasn’t ready, and he was too good for me.”

After a brief stint with actress Claire Forlani, Pitt was set up on a blind date with Jennifer Aniston in 1998. The two quickly hit it off and were dubbed Hollywood’s latest golden couple. The Morning Show star tied the knot with Pitt in 2000, and her man made a guest appearance on Friends the following year. Although Aniston had revealed hopes of starting a family with the Fight Club star, their union ended before they had the chance.

In January 2005, the couple formally announced their separation. “We would like to explain that our separation is not the result of any speculation reported by the tabloid media,” the pair said at the time. Their divorce was finalized nine months later.

Aniston wasn’t the last woman to steal Pitt’s heart. After meeting on the set of Mr. and Mrs. Smith in 2004, the actor struck up a romance with his costar Angelina Jolie. Pitt eventually adopted Jolie’s kids, Zahara and Maddox, in 2006 before welcoming daughter Shiloh the same year. The couple also share adopted children Pax, Vivienne and Knox. All of their kids accompanied Jolie and Pitt to their dreamy French wedding in 2014. Two years later, the beloved couple split.

Scroll down to learn more about Pitt’s star-studded love life!

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This story originally appeared on: US Magazine - Author:Meredith Nardino