What Brad Pitt's Exes Have Said About Him

Brad Pitt's romantic life has been even more scrutinized than his acting career. He has been married twice, and lately, there have been telltale signs that Brad Pitt is planning to tie the knot with his current girlfriend, Ines De Ramon. The twice-named People Magazine's Sexiest Man of the Year star has left a trail of exes in his wake, and many of them have spoken up about their relationship with him. When a celeb is as famous as Pitt, every second of his dating life is sure to be picked over and studied. 

The "Seven" actor had a contentious breakup with his second wife, Angelina Jolie, whose own relationship with the star started in controversy. However, many of Pitt's exes speak lovingly of their time with him, including his first ex-wife, Jennifer Aniston. Despite how their marriage ended, the "Friends" star still has love for her ex-husband, and there have also been signs that Brad Pitt will never truly get over Jennifer Aniston either.

Over the decades, many of Pitt's former flames have offered an inside glimpse of what it's like to date one of the most famous men in the world. Who dumped him for a hair metal band lead singer? Who regrets breaking up? From his high school sweetheart in Missouri to his glamorous movie star ex-wives, here's a look at what Brad Pitt's exes have said about him.

Brad Pitt's romantic journey began in his hometown of Springfield, Missouri. In a 2014 interview with The Daily Mail, the actor's childhood sweetheart, Kim Bell (née Hubbard), talked about what it was like to date the hunky star when he was just a teenager back in the 1970s. Pitt and Bell dated in middle school from ages 13 to 15. "He was a good first boyfriend, those are your growing up years," said Bell, adding, "That was a lifetime ago, now he has six kids and I have two."  

According to Bell, it was easy to see that Pitt had that elusive "it" factor. "I think everybody knew he would be successful in whatever he would do," revealed Bell. "I just knew. He just had a personality that attracted people, he had leadership skills and he was sweet and kind."

Bell said she hadn't seen the "Fight Club" star since high school, but she does run into his parents from time to time. The mother of two isn't sad that she didn't end up with the Oscar winner. "I felt particularly lucky that I married my husband and had a life with him." Tragically, Bell's husband passed away from ALS in 2013.

In the mid-1980s, Brad Pitt was a struggling actor gaining traction with small roles in movies and guest spots on television shows like "Another World" and "Growing Pains." But in 1986, the future Oscar winner met UK pop star Sinitta Renet Malone, AKA Sinitta. She originally turned down an opportunity to meet the then-unknown actor until she saw a picture of the heartthrob. "Later that day, though, I saw pictures of this gorgeous boy on the desk," she told The Sun (via Smooth Radio). "I was like, 'OK, yes. Get him on the phone.'"

For Sinitta and Pitt, it was an instant match. "We met and just clicked," added the "So Macho" singer. "We were both quiet people, Christian, normal and healthy people underneath our crazy, public lifestyles and, at that point, he wasn't really, really famous. He was just the hottest boy — drop dead gorgeous."

Alas, their love was not meant to be, and the singer blamed long distance as the main reason for their 1988 breakup. In 2011, Sinitta was a contestant on "I'm a Celebrity ... Get Me Out Of Here!" where she discussed her past with the "Moneyball" star. "I saw him for two years," stated Sinitta (via Marie Claire UK). "He was fun, he was young and very sweet. Some ardent fan gave me a slap when I came out of a supermarket over that relationship." Of course, when Pitt landed his hunky breakout role in "Thelma & Louise" in 1991, Sinitta felt some regret. "I saw that movie and thought 'Oh my God, what have I done?'," she joked.

In 1989, Brad Pitt co-starred in the black comedy horror film "Cutting Class." He and his co-star Jill Schoelen started dating, and the pair even reportedly got engaged. The smitten actor went to visit his fiancée on set in Hungary, but instead of a joyous reunion, Schoelen informed him that she was in love with the film's director. The pre-fame actor had spent most of his remaining cash on a plane ticket, just to get dumped. "I spent my night in Budapest, sitting on a bench, smoking, with just a local bum to talk to who couldn't speak English," Pitt told The Sun in 2011 (via SheKnows). "These are the days and nights you remember when you have success. I returned to America absolutely broke."

Adding insult to injury, in 2013, Radar Online unearthed a few love letters that the enamored actor sent to Schoelen. "I adore you. I will love you forever," wrote Pitt. A second letter read, "I can't stop thinking about you. I don't feel complete without you next to me." 

But Schoelen appreciated her former flame's prose. "Brad wrote me one of the most beautiful poems a man can write a woman," Schoelen told Radar Online. "I thought he was so deep and soulful." Thankfully, by the time the love letters were published in 2013, Pitt was doing just fine. He was one of the biggest movie stars in the world and in a relationship with Angelina Jolie.

About a year after Brad Pitt had his heart crushed by Jill Schoelen, he started dating voice actress, singer, and actor Elizabeth (E.G.) Daily. The "Valley Girl" star talked about Pitt in an episode of "E! True Hollywood Story," "My first impression of Brad was that he was a very deep-souled guy," Daily said. "He was very up and coming. I just knew that he was super cute, and there were a lot of things that we connected on."

Daily and Pitt ended their relationship in 1989 but stayed friendly. Daily knew that Pitt had the goods to be a superstar. "I think he was really intense about his work," she added. "When you saw him, it was more like seething in him underneath. What I could feel from him was a really strong, visceral drive towards something really big."

In 2016, Angelina Jolie alleged that Pitt was physically and verbally abusive during an incident on a private plane, but Daily came out in defense of her former flame. "Brad isn't an aggressive man. Not at all," she told the Daily Mail. "I haven't been hanging out with him, and I don't know the circumstances, but I know Brad doesn't behave in that kind of manner." She added, "He's very laid back, very earthy." No charges were ever filed against Pitt. 

Brad Pitt and Robin Givens were an item in the late 1980s, and the "Seven" star was still trying to break into Hollywood at the time. "He was always such a wonderful person," Givens told Hollywood Life in 2019. "We met in acting class. I was doing 'Head of the Class.' We really both loved acting. He couldn't get a job."

Pitt wound up guest-starring in a 1989 episode of "Head of the Class" where he played a hunky character named Chuck. "We were in acting class and then he was booked on 'Head of the Class,' which is how we met the second time. I was like, 'Wait, you were just in Tuesday's acting class.'" Pitt and Givens, who was separated from Mike Tyson at the time, started a brief romantic relationship.

Tyson claimed in his memoir "Undisputed Truth" that he saw Pitt and his soon-to-be ex-wife in bed together. The former boxer has told varying versions of the story on subsequent interviews, one time claiming Pitt and Givens were just inside a car together in her driveway. Tyson seemed good-natured about it. He said on "The Real" in 2016, "I didn't really catch them in the act — maybe before the act ... He's a really nice guy." Givens denied the allegation that her ex-husband caught them in bed. 

A look back at Christina Applegate's fling with Brad Pitt shows that rock stars trump up-and-coming movie stars. In 1989, rock and roll was at its peak of popularity, largely thanks to MTV. Also in 1989, the relatively new network Fox had a massive pop culture hit with its anti-family sitcom, "Married... with Children." The breakout star of the show was its teenage bad girl, played by Christina Applegate, and the sitcom star showed up to the VMAs that year with Pitt.

The "Troy" star was not only Applegate's date that evening, but he also drove her mother and friend to the show. However, the future Oscar winner did not leave the event with the girl who brought him. Applegate, who was 17 at the time, talked about the diss in her memoir, "You With the Sad Eyes." "I felt so powerful and sure of myself for once that when the awards show was over, I left with Sebastian Bach, not Brad Pitt," Applegate wrote (via Yahoo Entertainment). "I hate to put it like this, but Brad back then was still making his way as an actor."

Applegate added, "We didn't talk for many years after that. Much later, but at different times, two of his movie star girlfriends asked me if it was true that I was the girl who left Brad behind at the MTV Video Music Awards. Brad had apparently told both of them separately that he was still mad at me."

Brad Pitt was still a couple of years away from his breakout role in "Thelma & Louise" when he starred in a 1990 made-for-TV movie called "Too Young to Die." Pitt met Juliette Lewis on the project when she was 16, and he was 10 years older. The pair embarked on a romantic relationship in 1989 (before their made-for-TV movie aired) that drew more and more public attention as the actors' careers boomed. In fact, looking back on the couple, Juliette Lewis and Brad Pitt's four-year relationship felt like an early '90s fever dream. The pair also teamed up for the 1993 crime thriller "Kalifornia," where they played a deranged, villainous couple on the run. However, they broke up that same year.

Lewis discussed their relationship in a 2006 interview with The Guardian. "It seems like a high-school relationship because now he's a very famous person," she said. "I look at this person that I shared a bit of history with. I hope he finds happiness because I genuinely loved him. He's a very stand-up, good guy. Four years was an eternity at that time." Lewis added, "It was my longest relationship and we both lost our anonymity together. Huge life changes all occurred, all connected to that person." For his part, Pitt echoed the sentiment in an interview with Vanity Fair in 1995. "I still love the woman. There's some real genius there ... It was one of the greatest relationships I've ever been in."

Next up on Brad Pitt's long list of exes is the tale of two Gen-X blonds. By the mid-90s, Pitt was a huge star in Hollywood, and he met an early-career Gwyneth Paltrow in 1994 on the set of David Fincher's devastating neo-noir "Seven" when she was 22 years old. "It was like major major love at first sight," Paltrow gushed during an interview on the "Call Her Daddy" podcast. "It was crazy."

The actors dated for three years and got engaged in December 1996. However, six months later, they called off the engagement. What led to the end of Gwyneth Paltrow's engagement to Brad Pitt? During her "Call Me Daddy" interview, Paltrow, who was only 24 years old when Pitt proposed to her, said that she still had a lot of growing up to do. It makes sense that Paltrow would be more hesitant, as Pitt is nine years older than her. Still, she looks back on their relationship as a notable time in her life. "He's a very intriguing character," the "Iron Man" star told Vanity Fair in 2025. "It's like having dated, I don't know, Prince William or something. That's always going to come up." Despite the breakup, Paltrow and Pitt have remained friendly, and they both confessed their lasting love for each other when she interviewed her former flame for a 2022 interview with Goop. 

In 1998, a year after his breakup with Gwyneth Paltrow, Brad Pitt met Jennifer Aniston. The "Ocean's Eleven" actor and the "Friends" star dated for about a year before becoming engaged. Their big Hollywood wedding took place in 2000, and the world fell in love with the couple.

In 2003, Pitt began production on the action comedy "Mr. & Mrs. Smith," co-starring Angelina Jolie. Pitt and Jolie played a married couple in the film, and their sizzling chemistry sparked rumors that the two megastars were having an affair, sending the tabloids into a frenzy. But whether there was an affair or not, Pitt and Aniston's marriage wasn't going well, and in 2005, they released a joint statement to People announcing their plans to separate. "We would like to explain that our separation is not the result of any of the speculation reported by the tabloid media." Jolie also publicly denied having an affair with her married co-star, though just one month after Aniston filed for divorce, Jolie and Pitt officially became a couple.

So what's the real reason Brad Pitt & Jennifer Aniston broke up? The "Fight Club" actor revealed in a 2011 interview with Parade that he was "trying to pretend the marriage was something that it wasn't." Aniston, on the other hand, has opted to take the high road, revealing in a 2005 interview with Vanity Fair, "I love Brad; I really love him. I will love him for the rest of my life. He's a fantastic man. I don't regret any of it, and I'm not going to beat myself up about it. We spent seven very intense years together; we taught each other a lot — about healing, and about fun." 

Just weeks after Brad Pitt's marriage to Jennifer Aniston ended, the "Seven" actor was photographed in Kenya with Angelina Jolie and her adopted son from Cambodia, Maddox Chivan. Brangelina soon became official, and the couple wasted no time adding to their family. They next adopted their daughter Zahara Marley from Ethiopia in 2005, and in 2006, Jolie gave birth to their second daughter, Shiloh Nouvel. The next year, the couple adopted their son Pax Thien from Vietnam, followed by the birth of their twins Knox Léon and Vivienne Marcheline in 2008. After six children, Pitt and Jolie finally decided to get married in 2014.

But this romance didn't have a happy ending. In 2016, Jolie filed for divorce and sought sole custody of the kids. Over the next eight years, the former couple was wrapped up in custody battles, abuse allegations, and property disputes. Their divorce was finalized in 2024, and currently, Pitt is reportedly estranged from all of his children — some of them have even removed his surname. It appears the relationship and breakup were difficult for the entire family. "I think my fighting spirit is finally back," Jolie told Variety in 2026. "I lost it for a bit. I got kind of taken down a little bit, and it's coming back in large part thanks to my children, who are now older, and encouraging it."