Angelina Jolie dating history: from Miller to Pitt and beyond. [Image Source: HOLA]
Angelina Jolie dating history includes a series of well-known relationships with actors Jonny Lee Miller, Jenny Shimizu, Billy Bob Thornton, and Brad Pitt, as well as rumored connections like Val Kilmer. Over nearly four decades, Jolie’s romantic life has been highly publicized, especially her decade-long partnership with Brad Pitt, with whom she shares six children.
Early Relationship and Marriage with Jonny Lee Miller
Angelina Jolie met British actor Jonny Lee Miller while filming the 1995 thriller Hackers. The two married in 1996 but separated a year later, with Jolie filing for divorce in 1999. Reflecting on the experience in a 1996 interview with The New York Times, Jolie said,
“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 their split, the two maintained a positive relationship. During a Q&A session at the 2025 Santa Barbara International Film Festival, Jolie shared,
“I do have a wonderful relationship with Jonny. He and I have sons the same age, and I’m so happy.”
Connection with Model Jenny Shimizu Amid Personal Exploration
Jolie encountered model Jenny Shimizu on the set of the 1996 drama Foxfire. Though the exact duration of their relationship remains unclear, Jolie opened up about the depth of her feelings for Shimizu in a 1997 interview with Girlfriends magazine, stating,
“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.”
During this period of self-discovery about her sexuality, Jolie explained her relationship with Miller, saying,
“He was around when I was figuring things out about myself, when I was realizing that I was attracted to women also,”
and added,
“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.”
Marriage to Billy Bob Thornton and Its Aftermath
Angelina Jolie met Billy Bob Thornton on the set of the 1999 film Pushing Tin. Despite Thornton’s reported engagement to Laura Dern at the time, the couple eloped in Las Vegas in 2000. During their marriage, Jolie adopted her first son, Maddox, in 2002. That same year, the couple separated, with the divorce finalized in 2003. Thornton has spoken warmly about their time together; in a 2025 interview with Rolling Stone, he said,
Image of: Angelina Jolie
“We simply split up because our lifestyles were so different.”
He also reflected,
“We had a great time together,”
and described their time as
“one of the greatest times of my life.”
Adding to this, Thornton revealed,
“She and I are still very, very close friends.”
Speculations Around Val Kilmer
Jolie’s role alongside Val Kilmer in the 2004 historical drama Alexander led to speculation about a possible romance, though neither confirmed it publicly. Kilmer later expressed admiration for Jolie in his memoir I’m Your Huckleberry. He wrote about his strong feelings, saying,
“I couldn’t wait to kiss Angie, buy her a Gulfstream jet, and have a V+J painted in rainbow glory on the tail,”
and reflected on her unique qualities:
“When people ask me what Angelina is like, I always say she’s like other women and other superstars but just more,”
explaining,
“More gorgeous. More wise. More tragic. More magic. More grounded.”
Long-term Relationship and Marriage with Brad Pitt
Angelina Jolie met Brad Pitt during the filming of Mr. and Mrs. Smith in 2003. At the time, Pitt was married to Jennifer Aniston, but by January 2005, he and Aniston had separated. By April 2005, Jolie and Pitt were publicly known as a couple after being photographed together on a trip to Kenya with Jolie’s son Maddox. Over the next several years, they built a large family with six children: Maddox and 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 magazine,
“It is a promise for the future, and their kids are very happy.”
Their wedding took place at their Frenchestate, Château Miraval, in 2014. However, Jolie filed for divorce roughly two years later, in 2016. Reflecting on the separation in a 2021 The Guardian interview, 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 a protracted legal process, their divorce was finalized in 2024. Jolie’s attorney told CNN,
“Frankly, Angelina is exhausted, but she is relieved this one part is over.”
Enduring Public Interest in Angelina Jolie’s Personal Life
Angelina Jolie’s personal relationships have long been a subject of public fascination alongside her prolific career as an actress, director, and humanitarian. Her dating history, marked by intense and high-profile romances, reflects both her evolving identity and the challenges of living in the spotlight. Now publicly single and focused on her creative work and family, Jolie’s journey illustrates the complexities of balancing personal life with a demanding public career.
BREAKING: Angelina Jolie and Brad Pitt were married Saturday in France, says a spokesman for the couple.
