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Angelina Jolie’s Dating History: From Jonny Lee Miller to The Weeknd

Angelina Jolie’s dating history is a captivating tale of romance, passion, and high-profile relationships with some of Hollywood’s biggest names.

From her whirlwind marriage to actor Billy Bob Thornton to her highly publicized relationship and eventual divorce from Brad Pitt, Jolie’s love life has been as intriguing as her illustrious career.

Jolie remains focused on her six children after her split from Pitt in 2016 after two years of marriage. However, her past romances, including her first marriage to Jonny Lee Miller and recent rumors linking her to The Weeknd, continue to fascinate fans. Known for her fiercely private nature,

Angelina Jolie’s dating history reflects her evolution from a rising star to a global icon, adding layers of intrigue to her already captivating persona.

The Weeknd (2021-Present)

Angelina Jolie and The Weeknd seen out together
Angelina Jolie & Weeknd

In 2021, rumors of a romance between Angelina Jolie and Grammy-winning musician The Weeknd (Abel Tesfaye) emerged after they were spotted together at multiple dinners in Los Angeles.

The pair reportedly bonded over their mutual interest in Ethiopia — Jolie’s daughter Zahara was adopted from the country, and The Weeknd has been involved in humanitarian efforts there.

Although neither party confirmed the relationship, speculation continued after The Weeknd released a song in which he references dating a movie star. Their brief public outings fueled interest, but any potential romantic connection seemed to fizzle out by early 2022.

Jonny Lee Miller (1995-1999)

Angelina Jolie and first husband Jonny Lee Miller
Angelina Jolie & Jonny Lee Miller

Angelina Jolie’s first marriage was to English actor Jonny Lee Miller, whom she met while filming the 1995 movie Hackers. The couple had an unconventional wedding in 1996, with Jolie famously wearing black leather pants and a white T-shirt on which she wrote Miller’s name in her own blood.

Despite their unique bond, their marriage was short-lived. The couple separated in 1997 and finalized their divorce in 1999. Despite their breakup, Jolie has maintained a deep respect for Miller, referring to him as a “solid man and solid friend.”

Jenny Shimizu (1996)

Angelina Jolie pictured with Jenny Shimizu
Angelina Jolie & Jenny Shimizu

During the filming of Foxfire in 1996, Jolie met model and actress Jenny Shimizu, and they shared a brief yet intense romantic relationship. In a later interview, Jolie confessed that she fell for Shimizu almost immediately.

She went as far as saying, “I probably would have married Jenny Shimizu if I hadn’t married my husband.” Although their romance didn’t last long, Jolie has spoken fondly of her connection with Shimizu over the years.

Read More: Gal Gadot and Yaron Varsano’s Relationship Timeline: From Meeting Jaron Varsano to Building a Life Together

Billy Bob Thornton (2000-2003)

Angelina Jolie and Billy Bob Thornton on a red carpet
Angelina Jolie & billy bob

One of the most notable relationships in Angelina Jolie’s Dating History was with actor Billy Bob Thornton. The pair met in 1999 while filming Pushing Tin, and they quickly eloped in 2000. Their relationship was marked by their eccentric displays of affection, including wearing vials of each other’s blood around their necks. The couple adopted Jolie’s first child, Maddox, from Cambodia in 2002. However, their whirlwind marriage ended abruptly in 2003.

After their split, Jolie had her tattoo of Thornton’s name removed and replaced it with the birth coordinates of her children. Despite the breakup, Thornton publicly praises Jolie, calling her a “wonderful person” and one of his closest friends.

Val Kilmer (2004 )

Angelina Jolie and Val Kilmer at a film event
Angelina Jolie & Val Kilmer

While there is no confirmed evidence of a romantic relationship between Angelina Jolie and Val Kilmer, rumors of a brief fling began after the pair worked together on the 2004 movie Alexander.

In his 2020 memoir I’m Your Huckleberry, Kilmer admitted to having a deep admiration for Jolie, even joking that he wanted to buy her a jet and paint their initials on it. Although their relationship remained platonic, Kilmer’s affection for Jolie adds an interesting chapter to her dating history.

Brad Pitt (2005-2016)

Angelina Jolie and Brad Pitt during their years together
Angelina Jolie & Brad Pitt

Perhaps Angelina Jolie’s most famous relationship was with actor Brad Pitt. The two met on the set of Mr. & Mrs. Smith in 2005, sparking rumors of an affair, as Pitt was still married to actress Jennifer Aniston at the time.

Shortly after, Pitt and Aniston divorced, and Pitt and Jolie became an official couple. Dubbed “Brangelina” by the media, their relationship dominated headlines for over a decade.

The couple adopted three children — Maddox, Zahara, and Pax — and welcomed three biological children: Shiloh, and twins Knox and Vivienne. After years of speculation, they got engaged in 2012 and tied the knot in a private ceremony in 2014.

However, in 2016, Jolie filed for divorce from Pitt, citing irreconcilable differences and requesting full custody of their children. The split led to a highly publicized custody battle, which continues to make headlines. Despite the emotional turmoil, Jolie has stated that her children remain her top priority.

Focus on Family (Post-2016)

Angelina Jolie spending time with her children
Angelina Jolie’s Focus on Family

Since her divorce from Brad Pitt, Jolie has largely remained focused on her family and humanitarian work. In interviews, she has emphasized that her six children are her main priority and that she is not actively seeking a new relationship.

In 2018, a source told PEOPLE magazine that Jolie wasn’t interested in dating and was fully devoted to raising her kids during their formative years. Though fans have speculated about potential romances, Jolie continues to keep her private life largely out of the public eye.

Conclusion

Angelina Jolie’s dating history reveals a complex, passionate, and sometimes tumultuous love life. From her early days with Jonny Lee Miller to her marriage and highly publicized split from Brad Pitt, Jolie’s relationships have evolved alongside her career.

Today, she remains an iconic figure, balancing motherhood, philanthropy, and her continued success in the film industry. While her romantic life may no longer dominate headlines, her journey through love, family, and personal growth continues to captivate fans worldwide.

For more information, be sure to check out our Celebrity Relations section.

FAQ (Frequently Asked Questions)

Q1: Who was Angelina Jolie’s first husband?

Angelina Jolie’s first husband was English actor Jonny Lee Miller, whom she married in 1996 after meeting on the set of Hackers.

Q2: Why did Angelina Jolie and Billy Bob Thornton divorce?

Angelina Jolie and Billy Bob Thornton divorced in 2003 due to their differing lifestyles. Thornton once explained that Jolie’s “global lifestyle” didn’t align with his more reclusive tendencies.

Q3: When did Angelina Jolie marry Brad Pitt?

Angelina Jolie and Brad Pitt got married on August 23, 2014, after being together for nearly a decade.

Q4: What are the names of the children that Angelina Jolie and Brad Pitt have together?

Angelina Jolie and Brad Pitt have six children: Maddox Chivan, Zahara Marley, Pax Thien, Shiloh Nouvel, and twins Knox Léon and Vivienne Marcheline.

Q5: Is Angelina Jolie currently dating anyone?

As of recent reports, Angelina Jolie is focused on her children and has not been linked to any serious romantic relationships since her split from Brad Pitt. Rumors about her and The Weeknd surfaced in 2021, but neither party confirmed a relationship.

Q6: What is Angelina Jolie and Brad Pitt’s combined net worth?

As of recent estimates, Angelina Jolie and Brad Pitt have a combined net worth of over $400 million, with Jolie’s net worth around $120 million and Pitt’s estimated at $300 million.

What is Angelina Jolie’s net worth?

As of 2024, Angelina Jolie’s estimated net worth is around $120 million. Her acting career, directing, producing, and endorsements accumulate this wealth.

Alexander Ross
Alexander Ross
Alexander Ross is GlamXGossip.com’s expert on celebrity relationships. His articles dive into the dynamics of high-profile romances, offering exclusive details and updates about the personal lives of stars. Alexander’s insights provide readers with an inside look at the relationships that make headlines.

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