Angelina Jolie is one of the most famous and influential actresses in Hollywood, known for her roles in films such as Lara Croft: Tomb Raider, Mr. & Mrs. Smith, Maleficent, and Eternals. She is also a humanitarian, a mother of six, and a former special envoy for the United Nations High Commissioner for Refugees.

But aside from her professional and personal achievements, Jolie has also attracted a lot of attention for her dating history, which spans over three decades and includes several high-profile relationships and marriages. Here is a chronological overview of Jolie’s love life, from her first husband Jonny Lee Miller to her rumored romance with The Weeknd.

Angelina Jolie and Jonny Lee Miller (1995-1999)

Jolie met her first husband, British actor Jonny Lee Miller, on the set of the 1995 film Hackers, where they played a pair of computer hackers who fall in love. The two got married in March 1996 in a small ceremony in New York, where Jolie wore black rubber pants and a white shirt with Miller’s name written in her blood.

However, the marriage did not last long, as they separated in September 1997 and divorced in February 1999. Jolie later said that they were too young and inexperienced to make the marriage work, but they remained good friends. In fact, Jolie was spotted having dinner with Miller in London in 2005, and she even visited him on the set of his TV show Elementary in 2014.

Angelina Jolie and Jenny Shimizu (1996-2000)

Around the same time she met Miller, Jolie also developed a close bond with her Foxfire co-star Jenny Shimizu, a Japanese-American model and actress. Jolie revealed in a 1997 interview with Girlfriends magazine that she was bisexual and that she had fallen in love with Shimizu at first sight. She also said that she would have married Shimizu if she had not married Miller. Shimizu later claimed that she and Jolie had an on-and-off affair for several years, even when Jolie was married to other men. However, Jolie never confirmed this, and their relationship seemed to fade away by the early 2000s.

Angelina Jolie and Billy Bob Thornton (1999-2003)

Jolie’s second husband was actor and filmmaker Billy Bob Thornton, whom she met on the set of the 1999 comedy-drama Pushing Tin. The two had a whirlwind romance and eloped in May 2000 in Las Vegas, just weeks after Thornton broke off his engagement to actress Laura Dern. Jolie and Thornton became one of the most eccentric and controversial couples in Hollywood, known for their public displays of affection, matching tattoos, and vials of each other’s blood that they wore around their necks.

They also adopted a son from Cambodia, Maddox, in 2002. However, their marriage soon fell apart, as they had different lifestyles and priorities. Jolie filed for divorce in July 2003, citing irreconcilable differences. The divorce was finalized in May 2004. Jolie later said that she and Thornton were still friends, but that they had nothing in common.

Angelina Jolie and Brad Pitt (2004-2016)

Jolie’s most famous and longest-lasting relationship was with actor and producer Brad Pitt, whom she met on the set of the 2005 action film Mr. & Mrs. Smith, where they played a married couple who were secretly assassins. At the time, Pitt was still married to actress Jennifer Aniston, but he and Jolie denied having an affair. However, Pitt and Aniston announced their separation in January 2005, and their divorce was finalized in October 2005.

Jolie and Pitt went public with their relationship in April 2005, when they were photographed together in Kenya with Maddox. They soon became known as “Brangelina”, one of the most powerful and glamorous couples in Hollywood. They also expanded their family, adopting a daughter from Ethiopia, Zahara, in 2005, and a son from Vietnam, Pax, in 2007. They also had three biological children, daughter Shiloh in 2006, and twins Knox and Vivienne in 2008.

Jolie and Pitt also collaborated on several films, such as A Mighty Heart, The Assassination of Jesse James by the Coward Robert Ford, and By the Sea. They also supported each other through various challenges, such as Jolie’s preventive double mastectomy in 2013, and Pitt’s alcohol addiction and anger issues. After being together for almost a decade, Jolie and Pitt finally tied the knot in August 2014 in a private ceremony at their estate in France, with their six children as their witnesses.

However, their marriage did not last long, as Jolie filed for divorce in September 2016, citing irreconcilable differences. She also requested sole physical custody of their children, sparking a bitter and lengthy custody battle that lasted until 2021, when they were finally declared legally single. Jolie later said that she divorced Pitt for the sake of their children’s well-being, and that they were still a family, but not a couple.

Angelina Jolie and The Weeknd (2021-)

Jolie’s most recent rumored romance is with Canadian singer and songwriter The Weeknd, whose real name is Abel Tesfaye. The two were first spotted having dinner together at Giorgio Baldi, a celebrity hotspot in Los Angeles, in June 2021. They were seen again at the same restaurant in July 2021, and then at a private concert by Mustafa the Poet in September 2021.

The nature of their relationship is unclear, as some sources claim that they are just friends who share a common interest in humanitarian work, while others suggest that they are casually dating and having fun. Neither Jolie nor The Weeknd have confirmed or denied their romance, but they have sparked a lot of curiosity and speculation among their fans and the media.