Brad Pitt's road to love: from Jennifer Aniston to Angelina Jolie and his latest girlfriend, Ines de Ramon
Brad Pitt has finally gotten serious following his 2016 split from Angelina Jolie.
While the 59-year-old actor has been romantically linked to a handful of women – including Emily Ratajkoswki – since his divorce, Pitt is now in his first "proper relationship" with jewelry designer Ines de Ramon.
Here's a look at Pitt's love life through the years as he gets serious with a new flame.
BRAD PITT IN FIRST SERIOUS RELATIONSHIP SINCE INTENSE ANGELINA JOLIE SPLIT: WHO IS INES DE RAMON?
Brad Pitt is in a "good place" and getting serious with Ines, who is 27 years his junior. The two have been dating for a year and spent time together this summer as Pitt filmed a Formula 1 movie in Europe.
"This is Brad’s first proper relationship since the divorce," a source told People magazine. "He introduces [Ramon] as his girlfriend" and "is doing great with Ines."
"It’s great to see him in a good place. Ines makes him very happy," the insider added.
Pitt's relationship with Ines was confirmed in November 2022, just months after her split with "Vampire Diaries" actor Paul Wesley. The two were married for nearly three years.
Pitt and Ines were first photographed attending a Bono concert together along with Cindy Crawford and Rande Gerber.
Angelina Jolie and Brad Pitt first became acquainted while filming "Mr. and Mrs. Smith" in 2003. At the time, Pitt was married to Jennifer Aniston.
"I didn't know much about exactly where Brad was in his personal life. But it was clear he was with his best friend, someone he loves and respects." Jolie recalled in an interview with Vogue in 2007. "It took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we'd earlier allowed ourselves to believe. And both knowing that the reality of that was a big thing, something that was going to take a lot of serious consideration."
By 2006, Pitt had split from Aniston and welcomed his first child with Jolie. The couple welcomed twins in 2008 and eventually got married at the urging of their children in 2014.
"It was important to us that the day was relaxed and full of laughter," Pitt and Jolie told People magazine. "It was such a special day to share with our children and a very happy time for our family."
However, their relationship quickly turned sour and Jolie filed for divorce from Pitt in 2016 after an argument between the two allegedly became physical. The abuse claim, which Pitt has denied, was also brought up in the couple's legal fight over their vineyard.
Brad Pitt was first introduced to Jennifer Aniston in 1994 by their managers. However, their friendship wouldn't turn romantic for a few years – the two went on their first date in 1998.
The couple announced their engagement while attending a Sting concert in November 1999. Pitt and Aniston married in 2000 during a beachside ceremony in Malibu.
While married, Aniston and Pitt co-founded the production company Plan B Entertainment. "We started this little company underground, didn't really talk about it because we didn't want to be accused of being actors who have vanity deals where you don't do anything," Aniston told The Guardian in a 2004 interview.
In 2004, Aniston announced she was ready to expand her family with Pitt. "It's time. It's time. You know, I think you can work with a baby, I think you can work pregnant, I think you can do all of it. So I'm just truly looking forward to slowing down," she told The Guardian.
Despite her plans to have a baby with Pitt, the couple announced their split a short time later.
"We would like to announce that after seven years together we have decided to formally separate," Pitt and Aniston said in a statement at the time. "For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration."
"We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months."
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Before his marriage to Jennifer Aniston, Brad Pitt experienced a whirlwind romance with Gywneth Paltrow.
The actors first met while filming the 1995 film, "Se7en." By 1996, Pitt was referring to Paltrow as his "angel" and the "love of [his] life," while accepting a Golden Globe for best supporting actor. The couple got engaged that same year.
"One night we were on the balcony of this house we were renting in this little town in Argentina," Paltrow recalled of their engagement in a 2023 episode of "Call Her Daddy." "I wish I remembered exactly what he said, but he proposed, it was fantastic, I was thrilled. We had talked about it, but I was surprised in the moment, I remember that. I must have been 24."
Paltrow and Pitt's engagement was short-lived and they two called it quits roughly a year later.
"I think I was a kid and I wasn't ready. He was too good for me," Paltrow admitted during a 2015 appearance on "The Howard Stern Show." "I honestly do think I was too young and didn't know what I was doing."
Brad Pitt dated co-star Juliette Lewis from 1989 until 1993. The couple co-starred on the films "Too Young to Die?" and "Kalifornia" together.
Pitt and Lewis dated for three years before calling it quits.
"I still love the woman. There's some real genius there. I had a great time with her… It was one of the greatest relationships I've ever been in," Pitt told Vogue two years later. "The problem is, we grow up with this vision that love conquers all, and that's just not so, is it?"
Lewis later recalled most of the press she got was "usually about Brad Pitt" or her drug addiction, "which hasn't been me since I was 22."
"I quit all my bulls--- at 22. There is growth. Get out of the past."
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Brad Pitt was romantically connected to his "Head of the Class" co-star Robin Givens in 1989. At the time, Givens was separated from her estranged husband, Mike Tyson.
Tyson wrote about Given's relationship with Pitt in his memoir, "Undisputed Truth." The former professional boxer claimed he had showed up to Givens' home to find her in a car with Pitt. Tyson also claimed he walked in on the actress and Pitt in bed together.
"Pulling up in the driveway, that part is true," Givens later admitted during a 2019 appearance on "Watch What Happens Live with Andy Cohen." "I didn't read the book, but I was told he says he caught us in bed, which never happened. Never, ever, ever happened."
Brad Pitt also dated voice actress Elizabeth "E.G." Daily in a short-lived 1989 romance.
Daily described Pitt as "deep-souled" during an episode of "E! True Hollywood Story."
"I think he was really intense about his work," Daily said. "When you saw him, it was more like seething in him underneath. What I could feel from him was a really strong, visceral drive toward something really big."