The Unconventional Love Life of Angelina Jolie: A Fascinating History

Angelina Jolie, the renowned actress, filmmaker, and humanitarian, is not only celebrated for her remarkable career but also for her unconventional and often captivating love life. With a history as intriguing as her roles on screen, let’s delve into the fascinating romantic journey of this iconic figure.

Racy past: Angelina Jolie had a romance with Jenny Shimizu and the pair starred together in 1996's Foxfire. 'I probably would have married Jenny if I hadn't married my husband,' Jolie revealed in an interview years later. 'I fell in love with her the first second I saw her'

Angelina’s first high-profile romance was with British actor Jonny Lee Miller. They met while filming “Hackers” and tied the knot in a unique ceremony where Angelina wore a white shirt with Jonny’s name written in her blood. This bold start set the tone for her love life, proving she was not one to conform to traditional norms.

The end: Angelina Jolie's shock split from Brad Pitt on Tuesday was just the latest chapter in a very colourful love life story

Perhaps the most publicized of her relationships was her marriage to actor and musician Billy Bob Thornton. Their whirlwind romance captured the media’s attention, and their shared eccentricities, including vials of each other’s blood worn as necklaces, solidified their status as one of Hollywood’s most unconventional couples.

Number one: She met first husband-to-be Jonny Lee Miller on the set of 1995's Hackers

Angelina’s relationship with Brad Pitt, often referred to as “Brangelina,” was one of the most talkedaout in Hollywood history. They met on the set of “Mr. Mrs. Smith” while Brad was still married to Jennifer Aniston, sparking widespread controversy. Despite this, their partnership endured for over a decade, with a marriage that included six children and a commitment to humanitarian efforts.

Switching sides: She split from the Brit when the film wrapped, which led her to her first same-sex relationship with model-actress Jenny Shimizu (bottom right), whom she met on the set of 1996's Foxfire

Following her high-profile divorce from Brad Pitt in 2016, Angelina has been focused on her children and her work. She’s dedicated herself to humanitarian causes, including her role as a UNHCR Special Envoy, and has continued to direct and produce films.

Back on: It was while filming Foxfire Jolie reconnected with Miller, eventually marrying in March 1996

One consistent theme throughout Angelina’s romantic history is her unwavering commitment to her family. As a mother to six children, three of whom are adopted, she has always prioritized their well-being.

Gross: She caused a stir when she was pictured kissing her brother Haven full on the lips backstage at the 2000 Golden Globes, doing the same three months later on the Academy Awards red carpet

In recent years, Angelina’s love life has been the subject of speculation, with rumors connecting her to various individuals. Regardless of her relationship status, she remains an influential figure in both the entertainment industry and the world of humanitarian work.

Close family: After picking up her first Oscar - Best Supporting Actress for Girl, Interrupted - she opened her acceptance speech by telling the crowd 'I'm so in love with my brother right now'

Angelina Jolie’s romantic history is a testament to her bold and unconventional approach to life and love. Her ability to capture attention both on and off the screen has solidified her status as a captivating and enigmatic figure in Hollywood, with a love life as captivating as her filmography.

Number two: That month she began dating Billy Bob Thornton, and two months later they married in Las Vegas

Love is: Jolie and Thornton - who is 20 years her senior - frequently made headlines with their frequent and outlandish declarations of love, famously wearing vials of each other's blood around their necks

On set again: The pair had met the previous year on their film Pushing Tin, in which she plays his young wife who cheats on him with rival John Cusack

Taken: Angelina and Billy Bob reportedly did not pursue a relationship during filming, as he was engaged to actress Laura Dern at the time

And another! Meanwhile she was rumoured to be dating yet another co-star: Timothy Hutton, with whom she appeared in 1997's Playing God

Drama: In 2005 she was accused of being the reason behind Brad Pitt's split from wife Jennifer Aniston

Pattern: The two reportedly hooked up while filming Mr And Mrs Smith

Small number: Despite rumours she had linked up with other co-stars throughout the years - including both Colin Farrell and Jared Leto during the filming of Alexander - Jolie has claimed she only slept with four men in her life; three of whom she married

Scroll to Top