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Brad Pitt isn’t just one of the most sought-after actors in Hollywood, he was, for a time, one of its most eligible bachelors! Over the course of the last few decades, Brad has been involved with a number of lovely leading ladies. From his earliest romance with Jill Schoelen to his marriage and subsequent divorce from Angelina Jolie, on to his rumored new interest in Emily Ratajkowski, Brad’s relationships have regularly garnered much media attention, with his marriage to Changeling star leading to the nickname “Brangelina.” While that’s his most well-known relationship, Brad has dated plenty of fellow A-listers. Throughout his career, the Fight Club star has been married twice, and he shares six kids with his ex-wife Angelina. Find out everything you need to know about Brad’s relationships here!
Jill Schoelen
One of Brad’s very first Hollywood romances was with his co-star Jill Schoelen, whom he met on the set of the 1989 film Cutting Class. Brad and Jill became involved while filming the whodunit movie about a murderer loose in a high school. The former couple’s relationship actually became so serious that Brad popped the question and the two became engaged in 1989! Unfortunately, their romance wouldn’t last and the two broke off their engagement after only three months.
Juliette Lewis
Juliette Lewis was Brad’s next Hollywood flame, who he fell for while working together on a number of projects. The were together for roughly three years, and starred in films like Too Young to Die? and Kalifornia, which came out in 1990 and 1993. Clearly, the two had a lot of love for one another while they were still together. Juliette, now 47, was roughly 17 when the two became involved. But after starring in two films together and living together for a time, Brad and Juliette called it quits in 1993.
Gwyneth Paltrow
Remember when Brad and Gwyneth Paltrow were together?! Another one of the actor’s co-stars, Brad and Gwyneth also had a lengthy relationship that lasted from 1994 to 1997. Like his two previous loves, Brad and Gwyneth starred in a project together: the 1995 Se7en. They dated for a total of three years, and even got engaged in 1996.
In their time, Gwyneth and Brad were one of the hottest couples of the ’90s, and they seemed to really be in love with one another, between Brad supporting Gwyneth and the two attending red carpet events and lighting up the screen. However, they called off their engagement by 1997. Since then, Gwyneth was married to Coldplay frontman Chris Martin, with whom she has two children, and is now married to producer Brad Falchuk.
Jennifer Aniston
Likely the most famous couple Brad was a part of, he began dating Friends star Jennifer Aniston in 1998. It wasn’t too long until the pair became engaged and Brad finally married the woman he loved! The two exchanged their “I do’s” in 2000, and all seemed right with the world, but five years later, their personal life was thrust directly into the spotlight.
In 2005, Brad starred alongside Angelina Jolie in the action-comedy Mr. & Mrs. Smith. The chemistry between the two was palpable and rumors began to swirl that Brad had cheated on Jen with Angie. Though the parties involved completely denied the speculation, Brad and Jen divorced in 2005. All these years later, however, Jen and Brad seem to have an amicable relationship. Jen went on to marry actor Justin Theroux in 2015, with the pair separating in 2017.
But Brad and Jen have still found ways to break the internet. Who could forget their now-infamous run-in at the 2020 Screen Actor’s Guild Awards? Not to mention how the two touched hands as they passed each other backstage after they both won honors in their respective categories!
Angelina Jolie
Finally, Brad’s most high-profile relationship, marriage, and divorce came with Angelina Jolie. The two got together after filming Mr. & Mrs. Smith and everyone went nuts over the hot Hollywood couple. The pair became so well known around the world that the media dubbed them “Brangelina.” Together, Brad and Angie have six children—three adopted youngsters—Maddox, 20, Pax, 18, Zahara, 17, and three biological children Shiloh, 16, Vivienne and Knox, both 14.
Given just how committed the two were to one another, it never really seemed to cross their minds to get married. But that changed when the two finally walked down the aisle in a beautiful, intimate ceremony in France on August 23, 2014. Just two years later, though, their relationship came to a shocking end when Angie filed for divorce in September 2016. Hollywood was totally thrown by the announcement, and the two have since endured a highly-publicized custody battle over their children. The divorce proceedings have been messy to say the least. Other than custody, the exes have engaged in other legal battles, including one over the Girl, Interrupted star selling her stake in the couple’s winery, which Angelina won.
Emily Ratajkowski
Given Brad’s history of relationships with stunning women, it comes as no surprise that he’s most recently been linked to supermodel and actress Emily Ratajkowski, 31, following her split from husband Sebastian Bear-McClard after four years of marriage. According to a September 26 report in Page Six, though the potential couple are not officially dating, they’ve been spotted out and about. Specifically, an insider reportedly told the outlet that the Gone Girl beauty and Legends of the Fall actor, 58, “have been seen a couple times together.” And while the source noted that “people have been speculating about this for a while,” they also said that Brad is not dating anybody,” and that he has “been seen with other people.” Still, the source added the tantalizing tidbit, “stay tuned.”
Adding to the speculation, a source told OK magazine back in August that, “He asked her out, and she said yes. She’s always thought Brad was cute, and the way she saw it, what did she have to lose?” That report took a step further, claiming the duo are “secretly dating,” and adding that it was still “early.” Emrata has a son, Sylvester Apollo Bear, who is 18 months old.