“The Unconventional Love Life of Angelina Jolie: A Journey through her Peculiar Romances”

Angelina Jolie had previously revealed that she had been sexually involved with only four men, three of whom were her husbands. Nevertheless, her sexual history is anything but ordinary and outshines even the most fantastical Hollywood stories. The actress, who is now 41 years old, has shocked the world by filing for divorce from Brad Pitt, citing “irreconcilable differences,” after just two years of marriage.

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 Jolie has had a colorful romantic history, including a relationship with Jenny Shimizu, who she co-starred with in Foxfire back in 1996. According to Jolie herself, she’s said that if she didn’t marry her husband, she might have ended up marrying Shimizu. However, her love life goes way back even before then; in fact, back to her preschool years. During this time, Jolie referred to herself and her friends as the “Kissy Girls”, showing her sexual tendencies even at a young age. She even created a game where she would give boys cooties and then proceed to kiss them until they were taking their clothes off. All of this behavior eventually got her into some trouble.

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

Angelina Jolie and Brad Pitt’s separation has brought another layer of complexity to their already tumultuous romance. Back when Jolie was just a teenager, she had her first sexual encounter with her boyfriend at the age of 14. Interestingly, Jolie’s mother permitted this to happen as she deemed it safer for them to engage in such activities within the confines of their home rather than risk being out on the streets. Jolie revealed this tidbit during an interview with Cosmopolitan in 2003. However, Jolie’s adolescence wasn’t all rosy as she grappled with self-harm and even developed a fascination with knives.

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

Angelina Jolie and Jonny Lee Miller first met on the set of “Hackers” in 1995. During an interview with OK magazine, Jolie shared that she was no longer satisfied with mere physical and emotional intimacy with her then-boyfriend and wanted something more. One day, in an attempt to connect with him, she took a knife and cut him. He responded by cutting her in return, and they exchanged something in the process. Both were drenched in blood, and it made Jolie’s heart race. After that, whenever she felt trapped, she would resort to self-harm. This was a phase when she felt daring and spontaneous, particularly after drinking a few beers. As a result, she has numerous scars from those incidents.

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

Once the movie was finished, the actress parted ways with her British partner and began a same-sex romance with model-actress Jenny Shimizu, whom she met while filming the movie Foxfire in 1996. At just 20 years old, she had already dabbled in a variety of drugs including cocaine, ecstasy, LSD, and her favorite, heroin. She credited her former husband Jonny Lee Miller for helping her overcome her tumultuous past. The two met during the making of the movie Hackers in 1995, and she revealed that their relationship was her first sexual experience since her first boyfriend.

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

While working on the movie Foxfire, Angelina Jolie and her co-star Jonny Lee Miller rekindled their past connection and eventually got married in March 1996. Miller was just one of many co-stars whom Jolie had been romantically linked with, whether it was just rumors or actual relationships. After finishing the film, Jolie began a same-sex relationship with model-actress Jenny Shimizu, whom she met during the same movie shoot. In an interview later on, Jolie admitted that if she hadn’t married Miller, she might have tied the knot with Shimizu instead because she fell in love with her right after meeting her.

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

Back in 2000, there was a lot of controversy surrounding a passionate kiss that was captured between actress, Angelina Jolie and her brother Haven. The image was taken backstage at the Golden Globes and then repeated again on the red carpet at the Academy Awards three months later. Many found the display quite distasteful. On her wedding day, Jolie wore an unconventional outfit consisting of black rubber pants and a white t-shirt with her groom’s name written in her own blood. However, this didn’t deter model, Jenny Shimizu from pursuing a relationship with her. According to Shimizu, their romance continued for several years, even while Jolie was dating other people. Shimizu described Jolie as an amazing, open-hearted person. Eventually, Jolie ended her marriage with Miller in February 1999 to pursue other relationships.

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'

During her first Academy Award win for Best Supporting Actress in the movie Girl, Interrupted, she took everyone by surprise by expressing her love for her brother at the beginning of her acceptance speech. The following year, she caused a stir when pictures surfaced of her kissing her brother Haven on the lips backstage at the Golden Globes and later on the red carpet at the Oscars. Soon after winning the Oscar, she began dating Billy Bob Thornton, and they tied the knot just two months later in Las Vegas. The pair met while working on Pushing Tin, where she portrayed his character’s young wife who has an affair with rival John Cusack.

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

During a certain month, Angelina began a romantic relationship with Billy Bob Thornton, and surprisingly they got married in Las Vegas just two months later. Contrary to popular belief, they did not start seeing each other while filming, as Billy was already engaged to actress Laura Dern, whereas Angelina was rumored to be dating her co-star Timothy Hutton from the movie Playing God released in 1997. The couple’s public display of affection, including Angelina’s tattoo of Billy’s name on her shoulder and their wearing of vials of each other’s blood around their necks, gained significant attention. They even announced their intention to adopt a child from Cambodia in 2002, but unfortunately, they separated only three months later.

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

Love has different ways of being shown, and Jolie and Thornton’s relationship is a perfect example. Despite the 20-year gap in age, they were famous for their unusual declarations of love, like carrying vials filled with each other’s blood as necklaces. This exceptional way of expressing affection grabbed the media’s attention and highlighted how strong their bond was.

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

Once again working together on set, these two actors had previously collaborated on the film Pushing Tin. It’s worth noting that in that flick, Jolie portrayed the unfaithful spouse of her co-star’s character, who had an affair with their rival played by John Cusack. In an interview, Jolie revealed that the sudden shift in their relationship caught her off guard, as they seemed to have nothing in common overnight. She also stated that she had no plans of getting romantically involved with anyone for at least seven to eight years. However, destiny had other plans. In 2005, there were rumors that Jolie and Brad Pitt were having a love affair while shooting Mr. and Mrs. Smith, which supposedly led to Pitt’s separation from his then-wife Jennifer Aniston. Although Jolie initially denied the rumors, she later admitted that she had fallen in love with Pitt while working together.

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

There has been speculation that Angelina Jolie and Billy Bob Thornton did not engage in a romantic relationship while working together on a movie. The reason being that Thornton was reportedly committed 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

In the past, rumors circulated that the actress was involved in a romantic relationship with her co-star Timothy Hutton. However, during an interview with Today in 1997, she expressed that she could never forgive being intimate with a married man due to her father’s infidelity towards her mother. She made it clear that cheating goes against her principles and that she would not be attracted to someone who is unfaithful. Despite this, the couple made their relationship official in 2006 when they announced they were expecting a child together. They have since welcomed six children and got engaged in 2012 before tying the knot on August 23, 2014.

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

In 2005, there were rumors that Angelina Jolie was the reason behind the separation of Brad Pitt and Jennifer Aniston. Despite rumors about her romantic involvement with co-stars like Colin Farrell and Jared Leto during the filming of Alexander, Jolie claims to have only been 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 confessing to having “friends with benefits.” She explained that after being single for two years, she decided to explore relationships with close male friends, which she considered to be a more mature way of engaging in romantic connections.

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

As per the reports, it is said that the two individuals supposedly started a relationship while working on the film Mr. and Mrs. Smith. While it may not be the usual way to meet someone, I personally prefer to have short romantic encounters with men in hotels and then head back home to attend to my son. This arrangement works best for me because it allows me to feel intimate and feminine without disrupting my family life. It’s important to note that these aren’t casual flings with strangers but rather with people I am familiar with. I have never engaged in one-night stands.

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

Despite rumors of romantic connections with her co-stars, such as Colin Farrell and Jared Leto while filming Alexander, Angelina Jolie clarified that she has only had a few partners – precisely four, with three of them being her husbands.

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