Angelina Jolie Dating History: From Brad Pitt To The Weeknd

Let's take a look at Angelina Jolie's dating history: From her marriage to Brad Pitt to her relationship with The Weeknd.

Updated on Feb 27, 2024  |  02:14 PM IST |  168.7K
Angelina Jolie (Image via imdb)
Angelina Jolie (Image via imdb)

Angelina Jolie, the captivating actress and humanitarian, has captivated audiences on screen and off. While many are familiar with her dedicated role as a mother of six, her journey through love has often sparked public curiosity. Today, we delve deeper than headlines, exploring the significant figures who have shaped her personal life.

Jonny Lee Miller (1996-1999)

Angelina Jolie and Jonny Lee Miller (Getty Images)

Jolie met English actor Jonny Lee Miller on the set of the 1995 film Hackers. Their connection was immediate, leading to a spontaneous wedding in 1996. However, their busy schedules and the demands of their careers challenged their relationship. Despite the unconventional elements surrounding their marriage, like Jolie wearing a white shirt with "Jonny" written in blood on the back, they ultimately separated in 1997. Though their marriage was short-lived, they finalized their divorce amicably in 1999 and have remained friends ever since.

Jenny Shimizu (1996)

Angelina Jolie reportedly developed a close bond with her "Foxfire" co-star, Jenny Shimizu, around the same time as her marriage to Jonny Lee Miller. The two met during the filming of the 1996 movie and, despite Jolie being involved with Miller, she expressed falling in love with Shimizu the moment she saw her. In a 1997 interview, Jolie openly discussed her evolving understanding of love and sexuality, stating that she "could have married Jenny Shimizu" if not for her marriage to Miller.


The relationship with Shimizu marked an important period of self-discovery for Jolie, who realized she was attracted to women as well. Despite the instant attraction, Jolie was also figuring things out about herself in relation to her sexuality. She mentioned that Miller took her feelings for Shimizu seriously and, in retrospect, she admitted she "probably would have married" Shimizu if not for her commitment to Miller.

The relationship with Shimizu was characterized by support, and Jolie later described herself as a very sexual person who loves whoever she loves, regardless of gender. While the details of the breakup are unclear, Jolie went on to have several serious relationships, including marriages to Billy Bob Thornton and Brad Pitt. Shimizu married brand consultant Michelle Harper in 2014.

Billy Bob Thornton (2000-2003)

Angelina Jolie and Billy Bob Thornton (Getty Images)

In 2000, while filming Pushing Tin, Jolie unexpectedly married actor Billy Bob Thornton. Their whirlwind romance and unconventional expressions of affection, including wearing vials of each other's blood, captivated the public. In 2002, they announced the adoption of their son Maddox from Cambodia, solidifying their commitment to building a family. However, challenges arose, and their marriage ended in 2003. Despite the separation, both Jolie and Thornton have maintained positive remarks about each other, highlighting the mutual respect that remains between them.

Val Kilmer

Angelina Jolie and Val Kilmer (Getty Images)

Their paths first crossed in 2004 while filming the historical epic "Alexander." Kilmer portrayed King Philip II of Macedon, father of Alexander the Great, while Jolie played Queen Olympias, Alexander's mother. The film, directed by Oliver Stone, saw them working together but didn't spark any immediate romantic connection.

Years later, according to Kilmer's recent memoir, "I'm Your Huckleberry," the actors reconnected and developed a deeper bond. He expressed his admiration for Jolie's strength and resilience, particularly during a challenging time when she was losing her mother, Marcheline Bertrand, to cancer. Kilmer mentioned being present for her during that period, offering support and finding comfort in her company.

In his memoir released in 2020, Kilmer opened up about his feelings for Jolie, describing her as "perhaps the most soulful and serious" of all his past loves. He also revealed his initial attempts to push for more romantic involvement in the film, proposing flashbacks showcasing their characters falling in love, which director Stone politely declined. While acknowledging his attraction, he clarifies that the relationship never truly blossomed beyond a brief connection and mutual respect.


Brad Pitt (2005-2019)

Angelina Jolie and Brad Pitt (Getty Images)

Undoubtedly the most high-profile chapter in Jolie's relationship history began in 2005. While filming "Mr. & Mrs. Smith," she met Brad Pitt. Their undeniable chemistry on-screen sparked rumors that soon turned into a confirmed relationship. The news sent shockwaves through Hollywood, as Pitt was married to actress Jennifer Aniston at the time.

Jolie and Pitt, dubbed "Brangelina" by the media, quickly became a powerful Hollywood couple. Their love story unfolded in the public eye, with their growing family taking center stage. They adopted two more children, Zahara and Pax, before welcoming their first biological child, Shiloh, in 2006. In 2007, they adopted Pax legally, and their family expanded further with twins Knox and Vivienne in 2008.

In 2012, Brangelina announced their engagement, and two years later, they tied the knot in a private ceremony at their French estate. However, their picture-perfect image began to fade in 2016 when Jolie filed for divorce, citing irreconcilable differences. The news sent shockwaves through the entertainment world, and a lengthy custody battle ensued.

However, the fairy tale took a dark turn in August 2016 when an alleged heated argument during a private flight with their children led to accusations of physical abuse. The FBI investigated the incident, clearing Brad of child abuse allegations.

The custody battle ensued after their separation, with Angelina initially having primary physical custody. In 2018, a judge ruled for Brad to have more time with the children, emphasizing the importance of both parents in their lives. However, the legal battle continued, with Angelina accusing the judge of not considering the children's input.

In addition to the custody battle, Brad and Angelina found themselves in a legal dispute over their French vineyard, Chateau Miraval. Brad sued Angelina for allegedly selling her shares without his knowledge, while Angelina's investment company filed a $350 million lawsuit against Brad for misusing company assets.

Despite years of legal battles, there is now a glimmer of hope as Brad and Angelina have agreed to mediation in their vineyard dispute. This decision offers a potential turning point in one of Hollywood's most bitter divorces. The couple's tumultuous journey highlights the complexities of high-profile celebrity divorces and custody disputes.

The Weeknd (2021)

In 2021, rumors swirled around a potential romance between Jolie and singer The Weeknd after they were spotted having dinner together. However, neither confirmed nor denied the speculation, leaving the relationship status unconfirmed. This potential association, while fleeting, further fueled public curiosity about Jolie's personal life.


Today, Jolie prioritizes her children and dedicates herself to humanitarian efforts. While her journey through love has been complex. Beyond her high-profile relationships, Jolie's unwavering commitment to humanitarian work and advocacy for refugees showcases her compassion and strength as an individual. As she continues her life's journey, she remains a captivating figure, inspiring millions with her talent, resilience, and dedication to making a positive impact on the world.


ALSO READ: 'I almost cut a piece of myself for your life': Did The Weeknd almost give Selena Gomez his kidney for her transplant back in 2017?


Who is Angelina Jolie in a relationship with now?
Angelina Jolie is not currently dating anyone.

Does Angelina Jolie have biological children?
She gave birth to her first biological child, Shiloh, in 2006. Then Jolie adopted Pax (who is actually her second-oldest child), and she gave birth to twins Knox and Vivienne in 2008.

How many kids did Angelina Jolie give birth to?
She gave birth to her first biological child, Shiloh, in 2006. Then Jolie adopted Pax (who is actually her second-oldest child), and she gave birth to twins Knox and Vivienne in 2008. The 47-year-old has six children, all of whom she shares with her ex-husband, Brad Pitt.

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