Angelina Jolie is one of Hollywood's highest-paid actresses, but her romantic life has been just as fascinating as her career. We're unpacking her dating history over the years - here's a look…
Born Into Acting
Some people are born into the lives they would choose for themselves, which certainly applies to Angelina. Born to parents Jon Voight and Marcheline Bertrand, perhaps Angelina was destined to act.
Her dad Jon is a well-known name in the film industry, with roles in Midnight Cowboy, Runaway Train, and Heat. Angelina’s mom Marcheline also acted in several films and series throughout the 70s and 80s. However, with the birth of Angelina and her older brother James, Marcheline retired from acting to care for her children.
Daddy Busy at Work
Angelina's mom and dad split up when the actress was very young, and her mom was wholly responsible for raising them. She told Vogue in 2002, "We weren't poor, but because I was the child of an actor, there was an idea that we had a lot of money." Despite their dad's success, Angelina jumped from different rental apartments.
Angelina and her dad’s relationship has always been fraught. She revealed that he left the family before she turned 1 when he cheated on their mother. For years, the father-daughter interactions only played out in front of the press. Angelina later legally dropped her father's surname Voight in favor of her middle name; Jolie.
To Act or Not To Act
Angelina’s dad may have used her to promote himself as a family man. Still, she showed interest in acting from early on. When the family temporarily relocated to NYC, Angelina insisted on attending the Lee Strasberg Institute, where she studied for 2 years before returning to Beverly Hills, which her mother could barely afford.
However, in 2015 Angelina revealed to Interview Mag that she had actually never wanted to be an actor, and it was actually “thrust” upon her by her mother, who dreamed of a successful acting career herself. She said, “I only realized about five years ago… I don’t really like being the center of attention.”
No Sucker 4 Skool
In Beverly Hills, Angelina constantly felt out of sorts in the wealthy neighborhood; and other students made her feel that way too. She was bullied for being skinny, wearing braces, and sporting big glasses. It didn’t help that her mother was encouraging her to take up a career in modeling, to no avail.
Angelina then transferred to a new high school for alternative kids that don’t fit into regular schools. She told Parade, “[The school is] where the bad kids go. I chose it. I was the punk outsider who nobody messed with. I was fearless.” By 14, Angelina had met her first serious boyfriend.
Angelina’s is Angelic No More
At 14, Angelina started dating and embraced her "punk" side by wearing only black, going to mosh pits, and getting tattoos. She told Harper's Bazaar, "I am still, at heart — and always will be — just a punk kid with tattoos." Angelina even lost interest in acting for a while, preferring to become a funeral director.
The actress told ABC News, "Early in my first sexual relationship, I got knives out and had a night where we attacked each other." She elaborated on the experience to OK Magazine, "We had an exchange of something, and we were covered in blood; my heart was racing." Everyone has their kink, right?
The One Who Started It All
Angelina’s mom allowed her then-boyfriend to live with them at their rental. She told Cosmopolitan, “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 admitted her mom “did the right thing; it kept [her] out of trouble.”
Given that she was allowed to live with her boyfriend, Angelina grudgingly attended school daily. Very little is known about the first boyfriend, not even his name, and Angelina has shared few details about him. Even though the relationship ended two years later, her mother’s acceptance meant she finished school at 16.
Mental Health Struggles
Throughout her teens and before her acting career took off, Angelina suffered from severe mental health problems. She revealed to Wuthering Jolie in 2004, "I couldn't feel a bond with another human being." Her self-infliction of pain was an effort to "connect" with other people.
The actress revealed to People she has "grappled with an eating disorder and insomnia" for many years. Angelina has also been very vocal about her substance abuse. In an interview in 1998, she divulged that she had done "just about every drug possible." She reportedly gave up her habit in the early 2000s.
Back to Hollywood
With her passion for life renewed, Angelina now set upon her goal of becoming an actress. She told Rolling Stone that she struggled to be taken seriously, constantly told she was "too dark" for roles. With no opportunities, she appeared in music videos for Lenny Kravitz, Meat Loaf, and The Lemonheads.
Angelina appeared in her brother James' film school shorts before she booked her first feature film role in Cyborg 2 (1993). A critical and commercial flop, the film went direct-to-video. After watching the movie, Angelina said she "threw up while her brother tried to console her" and "didn't audition again for another year."
Hackers
After a year hiatus, Angelina returned with a vengeance. She booked her first leading role in a feature in the 1995 film Hackers. Roger Ebert of the Chicago Sun-Times called Angelina "a revelation." He added, "She's feisty, magnetic, and scene-stealing." The film has been recognized as Angelina's breakthrough role.
While the film didn't break even at the box office and received lacking reviews, many years later, Hackers earned itself a cult status. Most importantly, Hackers was when Angelina met Johnny Lee Miller, the actress' first relationship since breaking things off with her high school boyfriend.
Bound By Blood
Given both the actor's relatively low profile before the release of Hackers, it was only after the two got hitched in 1996 that the press seemed to give the relationship any attention. By the time Angelina and Johnny tied the knot, Angelina was only 20 years old and on the cusp of widespread prominence.
The actress detailed the impromptu wedding to The Sun, "We went for a quick wedding…I went in black leather pants. He stuck a veil on me at the last second and put a garter on the pants." She also reportedly wore a white shirt with Johnny's name written in blood on the back.
Love Is Love Is Love
The actress didn't only have eyes for her husband at the time. Model and actress Jenny Shimizu caught Angelina's eye on the set of Foxfire in 1995. Angelina spoke with Girlfriends in 1997. At the time, Angelina and Johnny had just started dating. She said, "I fell in love with [Jenny] the first second I saw her."
She added, "I probably would have married Jenny if I hadn't married my husband." Angelina revealed that she was open with Johnny about her love for Jenny. In Angelina's mind, he "took it seriously" and "didn't treat it just like some sexy thing." This was the first time Angelina admitted she liked women to press.
Divorce With Johnny
18 months after Johnny and Angelina tied the knot, they announced their intentions to separate, and the divorce was finalized in 2000. Angelina blamed herself for the breakdown of their marriage, telling the Calgary Sun she struggles to be "present enough, physically or emotionally, in relationships to get serious."
The pair remained good friends and insisted that the split was amicable. They were even spotted hanging out with each other years later. Angelina revealed to The Mirror, "Johnny and I never fought, and we never hurt each other. I really wanted to be his wife. I really wanted to commit."
A Name to Remember
While Angelina’s romantic life was in turmoil, her career began to flourish. The actress received a Golden Globe for her performance in George Wallace (1997). Angelina then dipped into TV, with the title character in HBO’s Gia (1998), earning herself an Emmy nomination.
Angelina’s career took off when she starred alongside Denzel Washington in The Bone Collector (1999). The film was the actress’ first real box office success, and critics responded well to her performance. By the time Angelina appeared in Girl, Interrupted (2000), she was as big as her dad had ever been.
Brotherly Love
Angelina won an Oscar for her role in Girl, Interrupted, and when she accepted her award, she said, “I’m so in love with my brother right now. He just held me and said he loved me.” After her win, she kissed her brother on the lips, which was captured in a widely shared photo.
While James insisted “it wasn’t a French kiss,” people were still shocked. The brother and sister were surrounded by accusations of incest. Angelina later clarified the meaning behind the affection to Vogue, “All that matters to me is that guy sitting right there who has stood by me and is so fucking happy for me.”
It's All About Angelina
With an Oscar win, slated performance in the Tomb Raider adaptation, and an onslaught of headlines about her, Angelina was the ‘It Girl’ of the early 2000s. By extension, almost everyone had eyes for the actress, even Mick Jagger. After collaborating on the video for Anybody Seen My Baby, Mick was fascinated with Angelina.
Angelina may have had a shaved head, but that didn’t stop the singer from developing feelings for her. He allegedly said, “She scares me a little - I like that.” Rumour has it the two went on a date that ended abruptly, with Mick leaving Angelina to have a one-night stand with actress Farah Fawcett. He really is the ladies’ man.
Silly Billy Bob
It wasn't long before Angelina had her sights set elsewhere. She met Billy Bob Thornton in 1999 on the set of Pushing Tin. At the time, Billy was living with and engaged to Laura Dern. However, that didn't stop Billy, 20 years her senior, and Angelina from courting and getting married after just two months of dating.
The couple wedded in a Las Vegas chapel in an utterly impromptu ceremony. While Angelina and Billy were loved up, Laura was left entirely in the dark and still engaged to a married Billy. Laura told Talk, "I left our home to work on a movie, and while I was away, my boyfriend got married, and I've never heard from him again."
Love in Overshare
To put it mildly, Angelina and Billy’s relationship was certainly interesting. For a self-entitled “agoraphobe,” Billy was out and about with Angelina, sharing intimate details of their private lives. Billy admitted to wearing Angelina’s underwear “occasionally” and discussed installing a padded room in their house.
In one instance, on the way to the MTV Awards, Billy told an interviewer he and Angelina had fooled around “in the car on the way.” Famously, the over-affection couple wore vials of each other’s blood in necklace vials. While the amount of blood stored in the vials was exaggerated by the press, people were already confused.
Jenny, Always
Even while Angelina and Billy were obsessed with one another, Angelina allegedly continued to see Jenny Shimizu from 1996 to 2000. Jenny wrote in her biography about Angelina, "She loves women too much. It's like a drug, and she was hooked. I was her first… I doubt I'll be the last."
Years later, Jenny invited Angelina to her wedding in 2014 because she "figured it couldn't hurt to invite her." However, either due to a busy schedule or perhaps she was too sad to see the woman she had loved marry someone else. Jenny added, "It would have been a really cool thing if she'd come." At the next wedding, Jenny!
A New Chapter
By 2002, despite thinking it was impossible she "could be anyone's mom," Angelina decided she was ready to be a mother. While playing with school children on location for Lara Croft: Tomb Raider in Cambodia, Angela told AP, "It was suddenly very clear to me that my son was in the country, somewhere."
Not only did the actress become tethered to Cambodia from understanding the deeply complex history of the country, but a year later, she returned to an orphanage in Battambang and adopted a child. Born as Rath Vibol, Maddox was 7 months old when Angelina took him to the States.
All Good Things End
Billy may have accompanied Angelina in 2001 to apply to adopt Maddox. However, the actress was signed as the sole parent to Maddox in 2002. There were rumors Billy had cheated on Angelina with his therapist, but it remains unconfirmed. The couple quietly divorced in the summer of 2002.
Billy told HFPA, "We just had different lifestyles. Hers is a global lifestyle, and mine is an agoraphobic lifestyle." Despite the abrupt end, the two stay in touch, and Angelina even wrote the foreword for Billy's memoir. She said, "The world would certainly be a hell of a lot more dull if that man weren't in it."
V+J in Rainbow Paint
In 2020, Val Kilmer released the biography I'm Your Huckleberry, where he detailed his former relationships and crushes, one of which he admits was Angelina. Val wrote, "I couldn't wait to kiss Angie." He even admitted to asking the director of Alexander (2004) to orchestrate a way for the two to lock lips.
Angelina later said on press for the film, "Val and I are close, professional friends...with the emphasis on professionalism." With no evidence the two dated, this alleged romance will stay in the rumor mill. Either way, even if Angelina and Val did exchange more than kisses, the actress had sights set elsewhere.
When Brad Met Angelina
Mr. and Mrs. Smith was expected to be the film of 2005, with two of the biggest stars in the world slated to play a couple. With credits like Fight Club, Seven, and Troy, Brad Pitt was one of the most bankable actors on the planet. Angelina replaced Nicole Kidman, who had dropped out of the project due to scheduling conflicts.
Angelina told People, "It took until, really, the end of the shoot for us, I think, to realize that it might mean something more than we'd earlier allowed ourselves to believe." While the two denied rumors for years that they had connected on set, Angelina later admitted to the NY Times that they "fell in love" on set.
Brennifer to Brangelina
There was one major issue: Brad was already married to Jennifer Aniston. Once considered the 'super couple' of Hollywood, the duo's courting, marriage, and appearances together were cherished, and the couple was labeled the first successful Hollywood couple. However, the fairytale ended after only 7 years of Brennifer.
6 months after Mr. and Mrs. Smith wrapped up shooting, rumors were ablaze of an affair between Angelina and Brad. What began as gossip was confirmed when Jen filed for divorce in 2005. Their joint statement said the separation was "not the result of any of the speculation reported by the tabloid media," but no one was buying it.
The Couple That Aren’t a Couple
Only months after announcing his split from Jen, Brad and Angelina were spotted on holiday with the actress' son. Jen spoke to Vanity Fair about her reaction to their relationship. She said, "The world was shocked, and I was shocked." Even with much to suggest Brad cheated on her, Jen revealed, "I choose to believe my husband."
Before Angelina and Brad publicly announced their relationship, they collaborated with W Magazine on a spread titled Domestic Bliss. It contained iconic photos of the duo playing house and caring for children. Just one year into their burgeoning romance, the couple journeyed to Ethiopia to adopt a child.
The Perfect Family
Angelina and Brad adopted Zahara from an orphanage in Addis Ababa in 2005; her birth mother later said she is “very fortunate.” Not long after returning to the States with Zahara, Brad announced his intention to adopt the rest of Angelina’s children, too. Maddox and Zahara’s surnames are changed from Jolie to Jolie-Pitt.
A year later, Angelina gave birth for the first time, and the couple welcomed Shiloh in 2006 in Namibia. Angelina and Brad adopted 3-year-old Pax from Ho Chi Minh, Vietnam, the following year. With four kids already to account for, the couple makes it six with the birth of twins Vivienne and Knox in 2008 in Nice, France.
Unsurprising Announcements
Only three years and three new children later, Brangelina finally announced they were a couple. Angelina and Brad revealed to Vogue in 2007 that the moment they decided to be a family was when Maddox called Brad "dad." Angelina said, "[Maddox] decided we would all be a family."
However, the couple had no intention of marrying anytime soon. Brad told Esquire, "Angie and I will consider tying the knot when everyone else in the country who wants to be married is legally able." On the other hand, their kids were insistent that Brad pop the question, encouraging him to "get mommy a ring!"
Nuptials and Support
While there was "no date set" at the time, Brad and Angelina were finally engaged after 6 years of dating. Angelina's ring was reportedly valued at $1 million and weighed 10 carats. The couple tied the knot in 2014 after same-sex marriage was legalized in 2013. For the first time, Angelina changed her surname to Jolie-Pitt.
Angelina revealed she had taken the necessary precautions to prevent herself from getting the same cancer that sadly took her mother's life in 2007. She wrote a piece for the NYT explaining her difficult decision. She also said, "I am fortunate to have a partner, Brad Pitt, who is so loving and supportive."
The End of Brangelina
Only two years later, Angelina shocks the world when she files for divorce from Brad. On top of that, she requested full custody of the children, with Brad only allowed visitation. From a source at People, the decision was made “for the health of the family.” Angelina was declared single in 2019 after a 13-year relationship.
While Brad was initially awarded more visitation with the children, the decision was overturned in 2021 after it was revealed Brad had relations with the judge. Angelina publicly addresses the split to the Guardian, stating, “It took a lot for me to be in a position where I felt I had to separate from the father of my children.”
Self-Focus or New Man?
Fans expected Angelina to be back on the dating market quickly with reports that she could be dating Irish actor Paul Mescal, 21 years her junior after they were spotted having coffee with daughter Shiloh in NYC. Rumors grew even more when Angelina and The Weeknd were spotted having dinner together, not once, but twice.
The Weeknd's new song Here We Go... Again, it featured the line "My new girl, she a movie star," leading fans to believe that Angelina and the singer had romanced. It's hard to say what is true and what is no more than gossip, but we can expect Ange to find the love we know she deserves!