Angelina Jolie, the Oscar-winning actress, has had a fascinating love life, with several high-profile relationships throughout her career. From her early romances to her turbulent marriages, Jolie’s love life has captivated the public’s attention. Let’s take a closer look at the relationships that have shaped her journey.

- Angelina Jolie has been in five serious relationships.
- Her first boyfriend, at the age of 14, played a significant role in her life.
- Jolie had a relationship with her Hackers co-star, Jonny Lee Miller.
- She explored new ground with her relationship with Jenny Shimizu.
- Jolie had rollercoaster romances with both Jonny Lee Miller and Billy Bob Thornton.
- Her highly publicized relationship with Brad Pitt, known as Brangelina, gained worldwide attention.
- After her divorce from Brad Pitt, Jolie focused on her children and remained single.
- There were brief rumors linking Jolie to musician The Weeknd in 2021.
Early Relationships and First Boyfriend
Angelina Jolie’s romantic journey began at a young age, with her first serious relationship occurring when she was just 14 years old. This early connection held significant meaning in her life, as her mother permitted her boyfriend to live in their house. Their relationship lasted for two years before Jolie decided to shift her focus towards pursuing her acting career.
After her first relationship ended, Jolie found herself in the midst of her blossoming career and exploring new opportunities. It wasn’t until she worked on the film Hackers that she found love again, this time with her co-star Jonny Lee Miller. Despite becoming romantically involved during the filming, their relationship faced challenges once the movie wrapped, leading to a loss of contact between the two.
Amidst the ups and downs of her love life, Jolie experienced a surprising turn when she began dating her Foxfire co-star Jenny Shimizu. This relationship marked a departure from Jolie’s previous experiences, as she had never considered being with a woman before. The unconventional connection with Shimizu challenged societal norms and expectations, showcasing Jolie’s willingness to explore new ground in her personal life.

However, Jolie’s story didn’t end with Shimizu. She then rekindled her romance with Jonny Lee Miller and the two decided to elope in 1996. This surprising turn of events stunned many, as Jolie and Miller exchanged vows in a small ceremony. Unfortunately, their marriage was short-lived, and they divorced just three years later.
Angelina Jolie’s early relationships set the stage for her captivating love life. From her first boyfriend at 14 to her tempestuous marriages and her high-profile relationship with Brad Pitt, Jolie’s journey has been marked by twists and turns. Stay tuned for the next sections where we will delve into her rollercoaster romance with Jonny Lee Miller and uncover the surprising marriage to Billy Bob Thornton.
Co-Star Romance with Jonny Lee Miller
Angelina Jolie found love on the set of Hackers with co-star Jonny Lee Miller, but their relationship faced hurdles beyond the silver screen. Their on-screen chemistry translated into a real-life romance, and they soon began dating. However, their relationship was not without challenges.
Despite their deep connection, Jolie and Miller found it difficult to maintain their relationship due to their conflicting work schedules. The demands of their respective acting careers often took them to different parts of the world, putting a strain on their bond. Eventually, they decided to part ways, but their love story remains a significant chapter in Jolie’s romantic history.
“The relationship with Jonny Lee Miller was very rooted in the ’90s,” Jolie revealed in an interview. It was a lot of trying to figure out who we were as actors, and husbands and wives, and it was a good thing to realize that we actually weren’t.
Despite the end of their romantic relationship, Jolie and Miller have maintained a friendship over the years. In fact, they reunited and shared a friendly moment at the premiere of Jolie’s film, First They Killed My Father, in 2017, showing that their bond extends beyond their past love affair.

| Relationship | Duration |
|---|---|
| First Boyfriend | 2 years |
| Jonny Lee Miller | On and off |
| Jenny Shimizu | Short-term |
| Billy Bob Thornton | 2 years |
| Brad Pitt | 12 years |
Sources: Vanity Fair, ELLE
Exploring New Ground – Relationship with Jenny Shimizu
Angelina Jolie’s romantic journey took an unexpected turn when she found herself attracted to her co-star, Jenny Shimizu. It was during the filming of their movie “Foxfire” that Jolie, who had never been interested in being with a woman before, started to develop a deep connection with Shimizu. Their on-screen chemistry translated into a real-life romance that surprised many.
This relationship challenged societal norms and expectations at the time, as same-sex relationships were not as widely accepted as they are today. Jolie’s willingness to explore her feelings and pursue a relationship with Shimizu showcased her fearlessness and authenticity. Despite the challenges they faced, Jolie and Shimizu shared a genuine bond that lasted for several years.

Their relationship withstood the test of time and served as a reminder that love knows no boundaries. Jolie’s openness about her feelings for Shimizu demonstrated her commitment to breaking down barriers and living life on her own terms.
Table: Angelina Jolie’s Relationship Timeline
| Year | Partner | Status |
|---|---|---|
| 1996 | Jonny Lee Miller | Married |
| 1999 | Billy Bob Thornton | Married |
| 2000 | Jonny Lee Miller | Divorced |
| 2001 | Billy Bob Thornton | Divorced |
| 2005 | Brad Pitt | Divorced |
Angelina Jolie’s relationship with Jenny Shimizu was a pivotal moment in her love life. It allowed her to explore her own desires and challenge societal expectations. Jolie’s willingness to embrace her feelings for Shimizu exemplifies her courage and authenticity in the face of adversity.
Rollercoaster Romance – Marriage to Jonny Lee Miller and Divorce
Angelina Jolie’s love story with Jonny Lee Miller took a dramatic turn when they eloped and then faced a heartbreaking split. The couple first met while filming the movie Hackers in 1995 and quickly fell in love. In a whirlwind romance, they decided to elope and got married in March 1996. Jolie made a statement with her unconventional wedding attire, wearing black rubber pants and a white shirt with Jonny’s name written in her own blood.
The union between Jolie and Miller seemed like a match made in Hollywood heaven, but unfortunately, their marriage faced its fair share of challenges. With both actors focused on their careers and spending long periods apart, maintaining a strong connection became increasingly difficult. As a result, Jolie filed for divorce in February 1999, just three years after their wedding.
Despite the end of their marriage, Jolie and Miller remained on amicable terms. In fact, they rekindled their friendship and have been seen supporting each other at various events and premieres over the years. Their rollercoaster romance may not have lasted, but the bond they formed during their time together remains a testament to the depth of their connection.

| Relationship | Duration | Status |
|---|---|---|
| Marriage to Jonny Lee Miller | March 1996 – February 1999 | Divorced |
| Relationship with Jonny Lee Miller | 1995 – 1996 | Dating |
| Relationship with Billy Bob Thornton | 2000 – 2002 | Divorced |
| Relationship with Brad Pitt | 2004 – 2019 | Divorced |
Surprising Marriage to Billy Bob Thornton
Angelina Jolie shocked the world when she tied the knot with Billy Bob Thornton, but their marriage was not destined to last. The couple met on the set of their movie Pushing Tin in 1999 and quickly became known for their eccentric and passionate relationship. They surprised everyone with their unique wedding ceremony, which included wearing vials of each other’s blood around their necks.
Despite the initial excitement and public displays of affection, Jolie and Thornton faced numerous challenges in their marriage. Their intense and unpredictable lifestyle, coupled with busy work schedules, put a strain on their relationship. In 2002, just two years after saying “I do,” the couple announced their separation and filed for divorce.
“Our relationship became a beautiful friendship,” Jolie reflected on her marriage to Thornton. “It was something that we both appreciated. I don’t regret any of it.”
The union with Billy Bob Thornton may have ended, but it was one of the many chapters in Jolie’s love life that added to her enigmatic persona. The actress has always been open about her unconventional choices, and her brief but intense marriage to Thornton is a testament to that.

| Partner | Relationship Period |
|---|---|
| First Boyfriend | 1989-1991 |
| Jonny Lee Miller | 1995-1997 (initially) and 1999-2000 (rekindled) |
| Jenny Shimizu | 1996 (fling while dating Jonny Lee Miller) |
| Billy Bob Thornton | 2000-2002 |
| Brad Pitt | 2005-2016 (relationship), 2014-2019 (marriage) |
The Brangelina Era – Relationship with Brad Pitt
The world watched in awe as Angelina Jolie and Brad Pitt became one of Hollywood’s most iconic couples, but their love story had its own share of challenges. Their relationship began on the set of the action-comedy film “Mr. & Mrs. Smith” in 2004. While Pitt was still married to Jennifer Aniston at the time, rumors of a connection between Jolie and Pitt soon began to circulate.
Jolie and Pitt, dubbed “Brangelina” by the media, quickly captured the public’s imagination with their undeniable chemistry and their shared humanitarian work. The couple adopted three children from different parts of the world and had three biological children together. Their family life appeared idyllic, creating the image of a picture-perfect Hollywood power couple.
However, behind closed doors, Jolie and Pitt faced their fair share of struggles. In 2016, Jolie shocked the world when she filed for divorce, citing irreconcilable differences. The custody battle over their children became highly publicized and contentious. Fans and the media were left stunned as the once inseparable couple navigated their way through a public divorce.
Despite the challenges they faced, Jolie and Pitt have remained committed to co-parenting their children and maintain a certain level of respect for one another. Their love story may have ended, but the impact they made on Hollywood and the world will not be forgotten.

| Angelina Jolie’s Relationships | Years |
|---|---|
| First Boyfriend | 14-16 |
| Jonny Lee Miller | 1996-1999 |
| Jenny Shimizu | 1994 (brief relationship) |
| Billy Bob Thornton | 2000-2003 |
| Brad Pitt | 2004-2019 |
Post-Divorce Life and Current Status
Following her high-profile divorce, Angelina Jolie shifted her focus to her children, embracing the role of a devoted single mother. With six children to care for, Jolie has made it her priority to create a stable and nurturing environment for her family. Despite the challenges of co-parenting with her ex-husband Brad Pitt, Jolie has remained committed to providing her children with love, support, and guidance.
Jolie’s dedication to her children can be seen through her involvement in various charitable and humanitarian efforts. She has continued her work as a UN Goodwill Ambassador and has used her platform to advocate for the rights of refugees and children affected by conflict. Jolie’s passion for making a difference in the world has undoubtedly had a profound impact on her children, instilling in them a sense of empathy and compassion.
While Jolie has maintained a low profile in the dating scene since her divorce, she has been linked to various rumors and speculations. Most notably, in 2021, there were rumors of a potential romance between Jolie and musician The Weeknd. However, neither party confirmed the relationship, and it remains unclear if there was any truth to the rumors.
As of now, Jolie’s current partner status remains undisclosed. However, it is evident that her focus lies in creating a stable and nurturing environment for her children, ensuring their well-being and happiness. Jolie’s unwavering dedication to her family and her commitment to making a positive impact on the world serve as an inspiration to many.
Angelina Jolie’s Post-Divorce Life and Current Status at a Glance
| Post-Divorce Life | Current Status |
|---|---|
| Shifted focus to her children | Undisclosed current partner |
| Continued involvement in charitable efforts | Rumored romance with The Weeknd in 2021 |
| Advocacy for refugee and children’s rights | Committed to creating a stable and nurturing environment for her children |
As Angelina Jolie continues to navigate her post-divorce life, one thing remains certain – her unwavering dedication to her children and her commitment to making a positive impact on the world. The talented actress and humanitarian undoubtedly has many more chapters to write in her life, and while her current partner status may remain undisclosed, her love for her family shines through in everything she does.

In 2021, Angelina Jolie briefly made headlines for her rumored connection to musician The Weeknd. The speculation began after the pair were spotted attending the same concert in Los Angeles. While there were no public displays of affection or official confirmations, their presence together sparked a flurry of rumors and grabbed the attention of fans and the media alike.
Angelina Jolie, known for her enigmatic persona, kept her personal life private during this period, leaving fans to speculate about the nature of her relationship with The Weeknd. The two talented artists have both captivated audiences with their work, and the possibility of a romantic connection between them only added to the intrigue.

While the rumors surrounding Angelina Jolie and The Weeknd fizzled out relatively quickly, their brief connection caused quite a stir in the entertainment world. As Jolie continues to focus on her children and her career, her love life remains a subject of immense curiosity and speculation for fans.
Recent Quotes:
“Love is such a precious and delicate thing. When rumors swirl, it’s important to remember that they often reveal more about our fascination with celebrity relationships than the truth itself.” – Tabloid Insider
“Angelina Jolie and The Weeknd attending the same concert ignited a wave of excitement among fans. While we may never know the true nature of their connection, it certainly got people talking and wondering. Such is the power of celebrity intrigue.” – Entertainment Magazine
Key Takeaways:
- In 2021, Angelina Jolie was rumored to have a romantic connection with musician The Weeknd.
- The rumors emerged after Jolie and The Weeknd were seen together at a concert in Los Angeles.
- Jolie, known for her privacy, kept details about her personal life under wraps, leaving fans to speculate.
- While the rumors faded, the brief connection between Jolie and The Weeknd caused a sensation in the entertainment world.
| Year | Relationship |
|---|---|
| 1996-1999 | Married to Jonny Lee Miller |
| 2000-2002 | Married to Billy Bob Thornton |
| 2005-2019 | Relationship and marriage to Brad Pitt |
Conclusion: A Complex Love Life Explored
Angelina Jolie’s love life has been a rollercoaster ride, filled with highs and lows, scandals and heartbreaks, leaving behind a legacy that is as captivating as her on-screen performances. From her early relationships and first boyfriend at the age of 14, to her co-star romances with Jonny Lee Miller and Jenny Shimizu, Jolie has never been one to follow societal norms.
Her rollercoaster romance with Miller included a whirlwind marriage and subsequent divorce, while her unexpected marriage to Billy Bob Thornton shocked the world. But it was her relationship with Brad Pitt, her Mr. & Mrs. Smith co-star, that truly captured the public’s attention. The formation of the Brangelina power couple and their combined family became the epitome of Hollywood glamour.
However, even the strongest connections can falter, as Jolie and Pitt’s relationship eventually faced challenges that led to their highly publicized divorce. Since then, Jolie has focused on her children and has not been interested in dating. Despite this, rumors briefly linked her to musician The Weeknd in 2021.
In conclusion, Angelina Jolie’s love life has been a journey filled with unexpected twists and turns. From her early relationships to her high-profile marriages and divorces, Jolie has defied expectations and embraced her own path. Whether it was her rumored feud with Jennifer Aniston, connections to Colin Farrell and Antonio Banderas, or her brave choice to explore relationships beyond societal norms, Jolie’s love life is as complex and intriguing as the characters she portrays on screen.
FAQ
Q: How many serious relationships has Angelina Jolie been in?
A: Angelina Jolie has been in five serious relationships throughout her career.
Q: Who was Angelina Jolie’s first boyfriend?
A: Angelina Jolie’s first boyfriend was when she was 14 years old.
Q: Did Angelina Jolie ever date a co-star?
A: Yes, Angelina Jolie has dated co-stars in the past.
Q: How many times has Angelina Jolie been married?
A: Angelina Jolie has been married three times.
Q: Who did Angelina Jolie marry in 2014?
A: Angelina Jolie married Brad Pitt in 2014.
Q: When did Angelina Jolie file for divorce from Brad Pitt?
A: Angelina Jolie filed for divorce from Brad Pitt in 2018.
Q: Is Angelina Jolie currently dating anyone?
A: No, Angelina Jolie is currently focusing on her children and has not been interested in dating.
Q: Was Angelina Jolie linked to The Weeknd?
A: Angelina Jolie was briefly linked to The Weeknd in 2021.
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