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Angelina Jolie’s rollercoaster love life as she jokes about being single at 45

Nearly five years after splitting from Brad Pitt, Angelina Jolie thinks she knows why she’s still “alone”.

The actress has been married three times; firstly to Jonny Lee Miller, then to Billy Bob Thornton before she tied the knot with Brad in 2014 after nearly a decade together.

The marriage crumbled in 2016 and she’s been single ever since.

Angelina recently opened up about her love life in a candid interview and admitted she’s worked out why she’s still on her own.

When asked recently if she has any dating no-nos before she decides to start up a romance, she told E! News’ Daily Pop: “I probably have a very long list. I’ve been alone for a long time now.”

However, she hasn’t always been single as we take a look back through her high profile romances.

Angelina Jolie has opened up about being single at 45

Jonny Lee Miller

Angelina married Trainspotting actor Jonny Lee Miller in 1996 when she was just 20 years old after meeting him on the set of their 1995 film Hackers.

Soon, their friendship turned to something more and they decided to get married in a civil ceremony in the Spring of the following year.

Speaking about the romance, she said at the time: “We both proposed to each other and both had questions to ask. I wondered if we should stay engaged for a while since he was going to be in Britain and I would stay in LA. But we went for a quick wedding.”

However, the wedding was far from the traditional white dress affair, as Angelina opted for a rather unusual choice of attire.

Wearing faux black leather trousers, Angelina borrowed her husband-to-be’s white shirt and had his name scrawled over the back of the shirt in his own blood.

Jonny Lee Miller and Angelina Jolie worked together on 1995 film Hackers
Jonny Lee Miller and Angelina Jolie worked together on 1995 film Hackers

After just one year of marriage, and a move from London to Los Angeles for Jonny, the couple decided to go their separate ways. The actress admitted at the time she “lost” herself being somebody else’s wife.

She shared: “You’re suddenly somebody’s wife. And you’re like, ‘Oh, I’m half of a couple now. I’ve lost me,'” she was quoted as saying. We went on some morning show, and they threw rice on us and they gave us toasters. I was thinking, ‘I need to get myself back.'”

Blaming herself for the split, Angelina admitted she wasn’t “present enough, physically or emotionally, in relationships to get serious”.

Billy Bob Thornton

Angelina Jolie and Billy Bob Thornton married in 2000
Angelina Jolie and Billy Bob Thornton married in 2000

As with Jonny, Angelina met her second husband on the set of another movie. This time it was whilst they played husband wife in the 1999 film Pushing Tin.

Their connection was instant and they married in 2000 in Vegas after a whirlwind romance – much to the shock of Laura Dern, who was engaged to Billy at the time.

Fans quickly branded their romance weird for their more unusual dedications to one another, such as planning his and her graves when they died and wearing a vial of blood from one another around their necks.

Defending the couple, she said: “People think they know a lot about our relationship. They know very little. What little they know, they’ve got pretty strong opinions about. Can’t help that.

“But I don’t think there’s anything weird about us … I’m just a very normal woman who is crazy about her man.”

Amid claims Billy was unfaithful whilst out on tour, Angelina started the process of adopting her first child – her son, Maddox – and she confessed it was “kind of tragic” that he wasn’t ready for that yet.

She explained: “He wasn’t ready, but he sent me his love. It’s kind of tragic.”

Eventually, they decided to go their separate ways for good – with Angelina deciding she wanted to focus on her humanitarian work and activism and Billy looking more towards his music.

She said: “In a year I became who I am today, very much, and he became who he is today. It was just totally different paths in life, and then we just looked at each other one day and we had nothing to say to each other.”

Brad Pitt

Angelina Jolie's most famous husband was Brad Pitt
Angelina’s most famous husband was Brad Pitt

The most famous of her romances – Angelina met Brad Pitt while he was still married to Jennifer Aniston and they became involved a short time later.

Whilst they quickly denied a relationship, having met on the set of ‘Mr. and Mrs. Smith’, they soon confessed they had “fallen in love” whilst working together.

It wasn’t until several months later when Brad and Jennifer announced they were divorcing, before Brangelina appeared in a number of photos for a magazine under an article titled “Domestic Bliss”.

When Angelina headed to Ethiopia in the summer of 2005 to adopt daughter Zahara, she was joined by Brad.

Brad went on to adopt Maddox and Zahara and the children’s surnames were changed to Jolie-Pitt to reference the new set up and the couple soon confirmed they were expecting their first child together.

Angelina Jolie and Brad Pitt
Angelina and Brad’s fairytale romance came to an end in 2016

Whilst things moved quickly with their growing family, it took a lot longer for them to get married as the couple wanted to wait until everyone was able to get married before they did.

Brad said: “We’d actually like to, and it seems to mean more and more to our kids. We made this declaration some time ago that we weren’t going to do it till everyone can. But I don’t think we’ll be able to hold out.”

Following the arrival of Shiloh, the couple decided to adopt again, this time flying out to Vietnam to bring Pax home.

And it was less than a year before they announced they were to become parents again – this time expecting twins, who they called Knox and Vivienne.

Angelina Jolie's rollercoaster love life as she jokes about being single at 45

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By 2014, the couple got married at a gorgeous Chateau in France with their six children a key part of the day, whilst at the end of the year, they started working on a movie together ‘By The Sea’.

However, things soon took a turn, despite Brad’s support as Angelina grappled with her health and had a preventive double mastectomy, and in August 2016, Angelina filed for divorce from Brad citing “irreconcilable differences” whilst also requesting full custody of their six kids.

Speaking about their split in 2020, Angelina said: “It was the right decision. I continue to focus on their healing. Some have taken advantage of my silence.”


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