THE RUNDOWNAngelina Jolie has spent nearly four decades in the public eye as an Oscar-winning actress, director, humanitarian, and mother of six—and the interest in her personal life has often been a notable part of her public narrative.While Jolie has been publicly single for years, focusing on her family and creative projects, the actress was linked to several fellow actors earlier in her career, including two early marriages to Jonny Lee Miller and Billy Bob Thornton, a high-profile romance with Brad Pitt, and a handful of rumored connections that were never confirmed.Below, a complete look at Jolie’s dating history through the years.Skip SectionJump toJonny Lee MillerJenny ShimizuBilly Bob ThorntonVal KilmerBrad PittJonny Lee MillerGregory Pace//Getty ImagesJolie met British actor Jonny Lee Miller while filming the 1995 thriller Hackers. The two married in 1996 but separated a year later. Jolie filed for divorce in 1999.In a 1996 interview with The New York Times, Jolie shared, “It was weird to immediately be married, and then you kind of lose your identity. You’re suddenly somebody’s wife. And you’re like, ‘Oh, I’m half of a couple now. I’ve lost me.’ We went on some morning show, and they threw rice on us, and they gave us toasters. I was thinking, ‘I need to get myself back.’”Despite the breakup, they’ve remained on good terms. During a Q&A at the 2025 Santa Barbara International Film Festival, per People, Jolie said, “I do have a wonderful relationship with Jonny. He and I have sons the same age, and I’m so happy.”Jenny ShimizuPatrick McMullan//Getty ImagesJolie and model Jenny Shimizu met on the set of the 1996 drama Foxfire. While the timeline of their relationship isn’t fully documented, Jolie reflected on how significant her feelings were in a 1997 Girlfriends magazine interview, saying, “I probably would have married Jenny Shimizu if I hadn’t married my husband. I fell in love with her the first second I saw her.”She also explained that she was navigating her own understanding of her sexuality at the time. “He was around when I was figuring things out about myself, when I was realizing that I was attracted to women also,” she said of Miller. “If anything, he took it very seriously. When I realized that somebody like Jenny could be a deep love for me, he realized it, and he took it very seriously.”Billy Bob ThorntonFrank Trapper//Getty ImagesJolie met Billy Bob Thornton on the 1999 set of Pushing Tin. Although Thornton was reportedly engaged to Laura Dern at the time, he and Jolie eloped in Las Vegas in 2000.The pair was still married when Jolie decided to adopt her first son, Maddox, in 2002. They separated that same year, and the divorce was finalized in 2003.Thornton has continued to speak warmly of their relationship. In a November 2025 interview with Rolling Stone, he said, “We simply split up because our lifestyles were so different.”Thornton shared that he and Jolie “had a great time together,” adding that the relationship was “one of the greatest times of my life.”“She and I are still very, very close friends,” the actor revealed.Val KilmerL. Cohen//Getty ImagesJolie and Val Kilmer co-starred in the 2004 historical drama Alexander, sparking speculation about a brief romance at the time. While neither commented publicly then, Kilmer later wrote in his memoir I’m Your Huckleberry that he had admired her deeply. “I couldn’t wait to kiss Angie, buy her a Gulfstream jet, and have a V+J painted in rainbow glory on the tail,” he wrote, per Us Weekly.“When people ask me what Angelina is like, I always say she’s like other women and other superstars but just more,” the actor continued. “More gorgeous. More wise. More tragic. More magic. More grounded.”The two never confirmed a relationship.Brad PittKurt Krieger - Corbis//Getty ImagesJolie met Brad Pitt while filming Mr. and Mrs. Smith in 2003. Pitt was married to Jennifer Aniston, but by January 2005, he and Aniston had announced their separation.In April 2005, Jolie and Pitt were photographed together on a trip to Kenya with Jolie’s son, Maddox, leading to confirmation that the pair was together.Over the next several years, they welcomed and raised six children: Maddox; Zahara, whom Jolie adopted in 2005; Shiloh, born in 2006; Pax, adopted in 2007; and twins Knox and Vivienne, born in 2008.The couple announced their engagement in 2012, with Pitt’s manager telling People, “It is a promise for the future, and their kids are very happy.”They married at their French estate, Château Miraval, in 2014. Roughly two years later, Jolie filed for divorce in 2016. In a 2021 interview with The Guardian, she said, “It took a lot for me to be in a position where I felt I had to separate from the father of my children.”After an extended process, they finalized their divorce in 2024. In a statement to CNN, Jolie’s attorney said, “Frankly, Angelina is exhausted, but she is relieved this one part is over.”