Honestly, trying to track who dated Angelina Jolie is like trying to map out a high-stakes Hollywood chess game. It’s never just a simple "dinner and a movie" situation with her. It’s vials of blood. It’s matching tattoos. It's secret weddings in rubber pants.
You’ve seen the tabloids. You’ve heard the rumors. But if you actually look at the timeline, the reality of her dating life is far more focused—and frankly, more intense—than the "serial dater" image people sometimes try to pin on her. Most of her big romances didn't start at a bar. They started on a film set, under hot lights, usually while she was playing someone else.
The Early Marriages: Blood, Leather, and Hackers
Before she was a global humanitarian icon, she was just a "wild child" with a penchant for the dramatic. Her first major relationship to hit the public radar was with Jonny Lee Miller.
They met on the set of Hackers in 1995. It was fast. It was 90s cool. They got married in 1996, and she famously wore a white shirt with his name written in her own blood on the back. She was 20. He was 23. They split after about a year of marriage, though the divorce wasn't official until 2000.
"I probably would have married Jenny Shimizu if I hadn't married my husband," she once told Girlfriends magazine.
That’s a detail people often skip. Around the same time as the Jonny Lee Miller era, Jolie fell for her Foxfire co-star Jenny Shimizu. It wasn't just a fling; she’s been open about the fact that she fell in love with Jenny the second she saw her. While they didn't head to the altar, it marked a significant moment in how she viewed love—it was about the person, not the gender.
The Billy Bob Era
Then came Billy Bob Thornton. This is the one everyone remembers because it was weird.
They met on Pushing Tin (1999) while he was actually engaged to Laura Dern. Talk about a mess. They eloped in Vegas in 2000 and spent the next few years being the most "extra" couple in Hollywood. The vials of blood around their necks? That was real. The massive "Billy Bob" tattoo on her arm? Also real.
But by 2002, the fire burned out. She adopted her first son, Maddox, and the relationship shifted. They divorced in 2003, with Billy Bob later saying they just had "different lifestyles"—he wanted to stay home, she wanted to see the world.
The Brangelina Decade
We have to talk about who dated Angelina Jolie without ignoring the absolute gravitational pull of Brad Pitt.
It’s 2004. Mr. & Mrs. Smith. The chemistry was so loud it basically broke the internet before the internet was even a thing. The problem? Brad was married to Jennifer Aniston.
The fallout was nuclear. For years, you were either "Team Jen" or "Team Angie." Despite the initial scandal, they stayed together for twelve years. They became a unit. A brand. They had three biological children and adopted three more. They didn't even get married until 2014—mostly because their kids kept asking them to.
The Breaking Point
The end of "Brangelina" in 2016 was a shock to the system. It wasn't a clean break. It was a multi-year legal war involving a French winery (Château Miraval) and complicated custody battles.
As of early 2026, the dust is finally settling. The divorce was finalized in late 2024, but the legal echoes regarding their assets have dragged on. Most of the kids are now adults, and the focus has shifted from "who's dating who" to "who's moving where."
Rumors vs. Reality: Who is She Dating Now?
Since the split from Pitt, the media has been desperate to pair her with someone. Anyone.
- The Weeknd: They were spotted grabbing dinner in LA a couple of years back. Fans went wild. Was it a date? A business meeting? Neither ever confirmed anything romantic.
- Paul Mescal: A coffee date in London sparked a million tweets, but it turned out to be just a friendly meet-up after his play.
- Akala: This is the most recent "big" rumor. She's been seen with the British rapper and activist multiple times in 2024 and 2025. Sources say they share a deep passion for social justice, but the "dating" label is still something she hasn't slapped on it publicly.
The Truth?
By all reputable accounts in 2026, Angelina is largely single. She’s focused on her kids and her move away from Los Angeles. She recently listed her $25 million Los Feliz mansion. She’s looking for a fresh start in Cambodia and Europe, far away from the "toxic" atmosphere of the LA paparazzi scene.
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What You Should Know About Her Dating History
If you're looking for patterns, they are easy to find. She falls for creative partners. She likes people who are as intense as she is.
- Set-Life Romance: Almost every major partner she's had was a co-star.
- Intellectual Connection: Lately, she seems more interested in activists and thinkers than Hollywood leading men.
- Independence: Since 2016, she has prioritised her role as a mother over being one half of a "power couple."
If you’re trying to keep up with her status, stop looking at the red carpets. Look at her humanitarian work. That’s where she’s spending her time. The days of wearing blood vials are over; the era of global impact and family privacy is what she’s actually dating these days.
To stay truly updated on her trajectory, keep an eye on her film projects like Maria and her fashion venture, Atelier Jolie. Her romantic life may be quiet, but her career is anything but. Moving forward, the best way to understand her is to watch her actions as she transitions out of Hollywood and into her next international chapter.