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The loves that didn't last

As Angelina Jolie gets set for shock divorce we take a look at her tangled love life from Billy Bob Thornton’s vial of blood to that lesbian fling

AS news of Angelina Jolie and Brad Pitt splitting up hits the headlines, we take a look back at the tangled love life of the actress.

From wearing a vial of her ex’s blood to dating women as well as men and being accused of breaking up marriages, Angie is no stranger to scandal when it comes to relationships.

 Ange and Brad have announced their split
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Ange and Brad have announced their splitCredit: Getty Images

Angelina had her first serious boyfriend when she was just 14.

Her mother even allowed them to live together in her home, with Ange revealing: "I was either going to be reckless on the streets with my boyfriend or he was going to be with me in my bedroom with my mom in the next room.

“She made the choice, and because of it, I continued to go to school every morning and explored my first relationship in a safe way."

She later compared this teen relationship to a marriage because it was so intense – and claimed the breakup compelled her to start acting when she was 16.

Jonny Lee Miller (1995 - 1999)

 Ange and Jonny were married in 1995
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Ange and Jonny were married in 1995Credit: Sky Premier

Ange and Jonny became romantically involved during the filming of Hackers in 1995.

Jonny is reported to have been Angelina’s first lover since her teenage relationship.

After production on the film ended, the pair didn’t stay in touch for many months after, but eventually reconnected and married on March 28, 1996.

 Ange and Jonny divorced in 1999
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Ange and Jonny divorced in 1999Credit: Ramey

Controversial as ever, Ange married Jonny while wearing black rubber trousers and a white T-shirt - which had the groom's name written in her blood across it - apparently she believed doing this would seal their marriage and mean that he would never leave her.

The pair separated in September 1997 and divorced on February 3, 1999.

Jenny Shimizu (1996)

 Angelina is said to have enjoyed a lesbian affair with Jenny
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Angelina is said to have enjoyed a lesbian affair with JennyCredit: Splash News

Angelina began a relationship with model-actress Jenny Shimizu on the set of 1996 film Foxfire.

Ange said of the relationship: "I would probably have married Jenny if I hadn't married my husband.

“I fell in love with her the first second I saw her."

Billy Bob Thornton (1999 – 2003)

 Angelina and Billy Bob were known for their public declarations of love
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Angelina and Billy Bob were known for their public declarations of loveCredit: Rex Features

Angelina married actor Billy Bob Thornton on May 5, 2000, in Las Vegas, following a two-month romance.

The couple met on the set of 1999 film Pushing Tin but didn’t pursue a relationship as Thornton was engaged to actress Laura Dern, while Jolie was reportedly dating actor Timothy Hutton.

The pair made an array of weird and wonderful public declarations of passion, most famously wearing one another's blood in vials around their necks.

The pair announced their separation in 2002 – just three months after announcing that they would be adopting a child from Cambodia together.

Brad Pitt (2004 – 2016)

 Angelina and Brad started in a controversial way
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Angelina and Brad started in a controversial wayCredit: Getty Images - FilmMagic

Ange’s most controversial and longest lasting relationship.

Brad and Ange allegedly started their romance on the set of 2005 film Mr. & Mrs. Smith – but both deny this was the case.

The relationship became a Hollywood scandal and was cited as the main reason for Brad's divorce from Friends star Jennifer Aniston.

While Angelina did deny the pair had an affair on set, she is also quoted as saying that they "fell in love" while making the film.

She added: "To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive.

“I could not look at myself in the morning if I did that. I wouldn't be attracted to a man who would cheat on his wife."

In January 2006, Angelina confirmed that she was pregnant by Brad and the couple went on to announce their engagement in April 2012.

The pair married on August 23, 2014, at their French estate.

However, the Hollywood actress has now filed for divorce citing irreconcilable differences and wants overall physical custody of their six children – not joint custody with Brad.

The couple have six kids together – Maddox, 15, Zahara, 11, Shiloh, 10, Pax, 12 and eight-year-old twins, Knox and Vivienne.

Other rumoured relationships:

Elizabeth Mitchell

 Not just on screen? Angelina and Elizabeth - who starred together in Gia - are rumoured to have dated in real life
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Not just on screen? Angelina and Elizabeth - who starred together in Gia - are rumoured to have dated in real lifeCredit: TNI Press

Timothy Hutton

 It is rumoured that Ange and Timothy hooked up on set of 1997 film Playing God. Apparently, he broke her heart
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It is rumoured that Ange and Timothy hooked up on set of 1997 film Playing God. Apparently, he broke her heartCredit: Ron Galella Collection

Colin Farrell

 Angelina is also rumoured to have dated Colin Farrell
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Angelina is also rumoured to have dated Colin FarrellCredit: Rex Features

Val Kilmer

 Angelina and Val are also rumoured to have had a fling
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Angelina and Val are also rumoured to have had a flingCredit: PA:Press Association


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