3 weddings and a ... blood vial? Angelina Jolie's eventful romantic history

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Blood vials! Cheating scandals! Angelina Jolie’s relationships have never been dull. With Entertainment Tonight reporting that the mom of six is dating again — amid her lengthy divorce from Brad Pitt — we look back at her romantic history, which has included married men, at least one (single) woman, and often a whole lotta drama.

<p>Angelina Jolie <a href="https://www.yahoo.com/entertainment/inside-angelina-jolie-apos-post-195220501.html" data-ylk="slk:reportedly has a new man in her life;outcm:mb_qualified_link;_E:mb_qualified_link" class="link rapid-noclick-resp newsroom-embed-article">reportedly has a new man in her life</a> — a year and a half after parting ways with third husband Brad Pitt. While the romance is “not serious,” the actress and director is seeing an “older-looking man who is a real estate agent,” according to <em>Entertainment Tonight</em>. “He isn’t a celebrity or high profile in any way.” The mom of six has been “secretive of her love life” — not that we blame her — and finds having another adult to spend time with to be “helpful.” Helpful is an odd word — will he be babysitting? — but we’ll go with it.<br>(Photo: Getty Images) </p>
Angelina Jolie is dating a real estate agent

Angelina Jolie reportedly has a new man in her life — a year and a half after parting ways with third husband Brad Pitt. While the romance is “not serious,” the actress and director is seeing an “older-looking man who is a real estate agent,” according to Entertainment Tonight. “He isn’t a celebrity or high profile in any way.” The mom of six has been “secretive of her love life” — not that we blame her — and finds having another adult to spend time with to be “helpful.” Helpful is an odd word — will he be babysitting? — but we’ll go with it.
(Photo: Getty Images)

<p>Her relationship with Brad Pitt was her most famous — Brangelina! — but mostly because they fell in love in 2004 on the set of <em>Mr. & Mrs. Smith</em> when he was still married to Jennifer Aniston. The tabloid darlings had a huge family (he adopted her two and they added four more) and waited years before getting married at their French estate in 2014. But all the Miraval rosé in the world couldn’t save their relationship, which ended with an explosive fight aboard a private plane that their eldest son, Maddox, had to bust up. Their parting of ways was messy — a battle over their kids — and they’ve yet to agree to a divorce settlement.<br><br>(Photo: Tony Barson/WireImage) </p>
Angelina Jolie and Brad Pitt

Her relationship with Brad Pitt was her most famous — Brangelina! — but mostly because they fell in love in 2004 on the set of Mr. & Mrs. Smith when he was still married to Jennifer Aniston. The tabloid darlings had a huge family (he adopted her two and they added four more) and waited years before getting married at their French estate in 2014. But all the Miraval rosé in the world couldn’t save their relationship, which ended with an explosive fight aboard a private plane that their eldest son, Maddox, had to bust up. Their parting of ways was messy — a battle over their kids — and they’ve yet to agree to a divorce settlement.

(Photo: Tony Barson/WireImage)

<p>In 2007, early on in Angelina’s relationship with Brad, she said that — despite her reputation as a maneater — she had only “slept with four men in my life — and I married two of them!” Her first husband was Jonny Lee Miller, the British actor whom she considers a “great friend.” They co-starred in 1995’s <em>Hackers</em> and eloped the next year. Her wedding ensemble was legendary because it was leather pants and a white shirt with Miller’s name across it — in her blood. “It’s your husband. You’re about to marry him,” she later told <a href="https://www.nytimes.com/1996/08/25/movies/following-ambivalently-in-mom-or-dad-s-footsteps.html" rel="nofollow noopener" target="_blank" data-ylk="slk:the New York Times" class="link rapid-noclick-resp">the<i> New York Times</i></a>. “You can sacrifice a little to make it really special.” They divorced in 1999.<br><br>(Photo: Jim Smeal/WireImage) </p>
Angelina Jolie and Jonny Lee Miller

In 2007, early on in Angelina’s relationship with Brad, she said that — despite her reputation as a maneater — she had only “slept with four men in my life — and I married two of them!” Her first husband was Jonny Lee Miller, the British actor whom she considers a “great friend.” They co-starred in 1995’s Hackers and eloped the next year. Her wedding ensemble was legendary because it was leather pants and a white shirt with Miller’s name across it — in her blood. “It’s your husband. You’re about to marry him,” she later told the New York Times. “You can sacrifice a little to make it really special.” They divorced in 1999.

(Photo: Jim Smeal/WireImage)

<p>Of course, there was also a blood sacrifice for husband No. 2, Billy Bob Thornton. Jolie got together with her <em>Pushing Tin</em> co-star — while he was still living with Laura Dern — and they eloped in 2000. In addition to her inking his name prominently on her arm, they wore vials of each other’s blood in matching necklaces. “We were apart a lot because she’s off making <i>Tomb Raider </i>and I’m making <i>Monster’s Ball</i>,” Thornton later said. “She thought it would be interesting and romantic if we took a little razor blade and sliced our fingers, smeared a little blood on these lockets and you wear it around your neck just like you wear your son or daughter’s baby hair in one.” OK then. Angelina’s time making <em>Tomb Raider</em> in Cambodia led to her adopting her first son, Maddox. And that spelled the end of limo sex with Thornton. Her hubby didn’t seem down with the decision, because soon after, in 2003, they split and Angelina finished the adoption process solo.<br><br>(Photo: Steve Granitz/WireImage) </p>
Angelina Jolie and Billy Bob Thornton

Of course, there was also a blood sacrifice for husband No. 2, Billy Bob Thornton. Jolie got together with her Pushing Tin co-star — while he was still living with Laura Dern — and they eloped in 2000. In addition to her inking his name prominently on her arm, they wore vials of each other’s blood in matching necklaces. “We were apart a lot because she’s off making Tomb Raider and I’m making Monster’s Ball,” Thornton later said. “She thought it would be interesting and romantic if we took a little razor blade and sliced our fingers, smeared a little blood on these lockets and you wear it around your neck just like you wear your son or daughter’s baby hair in one.” OK then. Angelina’s time making Tomb Raider in Cambodia led to her adopting her first son, Maddox. And that spelled the end of limo sex with Thornton. Her hubby didn’t seem down with the decision, because soon after, in 2003, they split and Angelina finished the adoption process solo.

(Photo: Steve Granitz/WireImage)

<p>Angelina also had a romance with actress and model Jenny Shimizu, with whom she appeared in the 1996 film <em>Foxfire</em>. In a 2003 interview with <em>20/20</em>, Jolie said she had been “surprised when I suddenly found myself having these feelings I always had for men, but for a woman, and wanting to kiss her and wanting to touch her.” She previously told <em>Girlfriends</em> magazine in 1997, “I would probably have married Jenny if I hadn’t married my [first] husband. I fell in love with her the first second I saw her.”<br><br>(Photo: Ryan McCune/Patrick McMullan via Getty Images) </p>
Jenny Shimizu

Angelina also had a romance with actress and model Jenny Shimizu, with whom she appeared in the 1996 film Foxfire. In a 2003 interview with 20/20, Jolie said she had been “surprised when I suddenly found myself having these feelings I always had for men, but for a woman, and wanting to kiss her and wanting to touch her.” She previously told Girlfriends magazine in 1997, “I would probably have married Jenny if I hadn’t married my [first] husband. I fell in love with her the first second I saw her.”

(Photo: Ryan McCune/Patrick McMullan via Getty Images)

<p>While Angelina has been linked to many other men (Colin Farrell, Jared Leto, Val Kilmer) — rumors helped along by her own bragging about various <a href="https://www.today.com/popculture/angelina-jolie-says-she-s-slept-four-men-wbna20893929" rel="nofollow noopener" target="_blank" data-ylk="slk:“lovers”" class="link rapid-noclick-resp">“lovers”</a> — her other serious romance was with Timothy Hutton, who we’ll assume is the last one on her list of four men. The timetable there, according to <a href="http://people.com/archive/early-to-wed-vol-53-no-20/" rel="nofollow noopener" target="_blank" data-ylk="slk:People" class="link rapid-noclick-resp"><em>People</em></a> magazine, was when she was separated from Miller around 1997, at the time this photo was taken. They appeared in 1997’s <em>Playing God</em> and later in 2006’s<em> The Good Shepherd</em>. They dated for a few years, long enough for her to get an “H” tattoo, for “Hutton,” before parting ways.<br><br>(Photo: Ron Galella, Ltd./WireImage) </p>
Angelina Jolie and Timothy Hutton

While Angelina has been linked to many other men (Colin Farrell, Jared Leto, Val Kilmer) — rumors helped along by her own bragging about various “lovers” — her other serious romance was with Timothy Hutton, who we’ll assume is the last one on her list of four men. The timetable there, according to People magazine, was when she was separated from Miller around 1997, at the time this photo was taken. They appeared in 1997’s Playing God and later in 2006’s The Good Shepherd. They dated for a few years, long enough for her to get an “H” tattoo, for “Hutton,” before parting ways.

(Photo: Ron Galella, Ltd./WireImage)

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