Angelina Jolie had previously disclosed that she had been romantically involved with only four men, three of whom were her spouses. Nevertheless, her sexual history is anything but ordinary and surpasses even the wildest tales from Hollywood. The 41-year-old actress stunned the world when she filed for divorce from Brad Pitt, her husband of two years, citing “irreconcilable differences.”
Angelina Jolie has had a colorful romantic past, which includes a relationship with her co-star from the 1996 film Foxfire, Jenny Shimizu. In fact, Jolie once revealed that she would have probably tied the knot with Shimizu if she hadn’t married her husband. However, Jolie’s romantic history predates this period, going all the way back to her preschool days. It was during this time that she and her friends called themselves the “Kissy Girls” and displayed an overtly sexual nature. Jolie even devised a game where she kissed boys and gave them “cooties,” which often led to more intimate activities. Unfortunately, Jolie’s behavior got her into trouble.
Angelina Jolie and Brad Pitt’s recent separation has added another layer of drama to their already eventful love story. According to an interview with Cosmopolitan in 2003, Jolie had her first sexual experience with her boyfriend at the age of 14, which was permitted by her mother, who believed it was safer for them to be at home rather than on the streets. However, Jolie’s teenage years were challenging, marked by instances of self-harm and a fascination with knives.
In 1995, Angelina Jolie met her future spouse Jonny Lee Miller while filming “Hackers”. During an interview with OK magazine, Jolie opened up about feeling unfulfilled with the mere physical and emotional aspects of her then-relationship. She craved something more. One day, in an attempt to feel closer to him, she grabbed a knife and cut him. Surprisingly, he cut her back and the exchance brought them closer. The experience made her heart race, and from then on, whenever she felt trapped, she would cut herself. This was a time when she felt adventurous and impulsive, usually after drinking a few beers. As a result, Jolie has several scars from those experiences.
After wrapping up the film, the actress parted ways with her British partner and began a same-sex romance with model-actress Jenny Shimizu, whom she met on the set of Foxfire in 1996. Despite being only 20 years old at the time, she had already dabbled in various drugs, including cocaine, ecstasy, LSD, and her personal favorite, heroin. She credits her former husband Jonny Lee Miller for helping her overcome her troubled past. The two met while filming Hackers in 1995, and she has openly shared that their relationship was the first sexual experience since her initial boyfriend.
While working on the movie Foxfire, Angelina Jolie reconnected with her co-star Miller and eventually got married in March 1996. This was just the beginning of a pattern that saw Jolie romantically linked to many of her co-stars, both in rumors and real-life relationships. After finishing filming, Jolie started a same-sex relationship with Jenny Shimizu, a model-actress who she met on the set of the same movie. Jolie even admitted in an interview later on that if she hadn’t married Miller, she would have most likely married Shimizu as she was smitten with her from the moment they met.
Back in 2000, there was a lot of controversy surrounding a photograph of a passionate kiss between Angelina Jolie and her brother Haven on the lips backstage at the Golden Globes. To make matters worse, she repeated the same action three months later on the red carpet at the Academy Awards. Quite frankly, it’s quite disgusting! On her wedding day, Jolie wore black rubber pants and a white tee with her groom’s name written in her own blood. Despite this unconventional attire, it didn’t stop Jolie from pursuing a relationship with model Jenny Shimizu. Apparently, their romance continued for several years, even while Jolie was seeing other people. Shimizu had nothing but kind words to say about Jolie, calling her an amazing and open-hearted person. Eventually, in February 1999, Jolie ended her marriage to Jonny Lee Miller and went on to pursue other relationships.
During her first Academy Award win for Best Supporting Actress in the film Girl, Interrupted, this actress shocked everyone by expressing her love for her brother at the beginning of her acceptance speech. The following year, she created controversy when photographs surfaced of her kissing her brother Haven on the lips backstage at the Golden Globes and later on the red carpet at the Oscars. Not long after receiving her Oscar, she began a romantic relationship with Billy Bob Thornton, and they tied the knot only two months later in Las Vegas. The two met while filming Pushing Tin, where she portrayed his character’s young wife, who has an affair with their rival, John Cusack.
During a particular month, Angelina began a romantic relationship with Billy Bob Thornton, and surprisingly, only two months later, the couple married in Las Vegas. Contrary to popular belief, their relationship did not begin during filming as Billy was engaged to actress Laura Dern at the time, while Angelina was rumored to be dating another co-star, Timothy Hutton from the movie Playing God, released in 1997. Their public displays of affection were headline-worthy, including Angelina’s tattoo of Billy’s name on her shoulder and the couple wearing vials of each other’s blood around their necks, which was quite unusual. In 2002, they announced their plan to adopt a child from Cambodia but unfortunately, their marriage ended just three months later.
Love can be shown in various forms, like the unconventional love story of Jolie and Thornton, who had a 20-year age gap but expressed their affection in peculiar ways. They made headlines for donning vials containing each other’s blood around their necks, which was an eccentric yet fascinating declaration of their love and reinforced the intensity of their bond.
The two actors, who had previously acted together in Pushing Tin, were reunited on set. Interestingly, in their previous collaboration, Jolie played the character of his cheating wife, who had an illicit affair with their rival played by John Cusack. In a recent interview, Jolie expressed her surprise at the sudden shift in their relationship, as they seemed to have nothing in common after their previous film. Additionally, Jolie stated that she had no intention of pursuing a romantic relationship for seven to eight years. However, fate had other plans, and rumors surfaced in 2005 that Jolie and Brad Pitt had become romantically involved during the filming of Mr. and Mrs. Smith. These rumors allegedly led to Pitt’s separation from his then-wife Jennifer Aniston. Although Jolie initially denied the rumors, she later confessed that she had fallen in love with Pitt while working together.
Reportedly, there were speculations that Angelina Jolie and Billy Bob Thornton did not engage in any romantic relationship during their time working on a movie. It is believed that this could be attributed to the fact that Thornton was already committed to actress Laura Dern at the time.
Speculations were going around that she was romantically linked with Timothy Hutton, her co-star in the film Playing God in 1997. However, during an interview with Today in the same year, she firmly stated that she could not pardon being intimate with a married man because of her father’s infidelity towards her mother. She emphasized that she would not find someone attractive if he cheated on his spouse as it went against her beliefs. Despite this, they acknowledged their romantic involvement in 2006 when she announced her pregnancy. After seven years and having six children together, they eventually got engaged in April 2012 and walked down the aisle on August 23, 2014.
In 2005, Angelina Jolie faced allegations that she was responsible for the split between Brad Pitt and Jennifer Aniston. Despite rumors that linked her to other co-stars, such as Colin Farrell and Jared Leto during the filming of Alexander, Jolie has claimed to have only been romantically involved with four men in her life, three of whom she married. However, in a 2004 interview with the New York Post, she appeared to contradict herself by admitting to having “friends with benefits”. Jolie explained that after being single for two years, she chose to pursue relationships with male friends, which she believed was a more mature way of engaging in romantic connections.
