Billy Bob Thornton is kind of a walking contradiction. He’s the guy who won an Oscar for writing Sling Blade, the raunchy anti-hero of Bad Santa, and currently, the gritty face of Taylor Sheridan’s Landman. But honestly, for a huge chunk of the public, he’s still just the guy who wore a vial of blood around his neck.
People love to talk about billy bob thornton dating habits because they used to be so chaotic. There was a time in the late '90s and early 2000s when you couldn't open a tabloid without seeing him. He was the poster child for whirlwind romances and "did they really just do that?" headlines. But here’s the thing: most of that is ancient history.
The Reality of Billy Bob Thornton’s Long-Term Love
If you’re looking for a fresh scandal, you’re going to be disappointed. Billy Bob has been with the same woman for over twenty years. Her name is Connie Angland. They met back in 2003 on the set of Bad Santa, where she was working behind the scenes in special effects.
They didn't rush to the altar. In fact, after five divorces, Thornton was pretty vocal about never wanting to get married again. He basically didn't want to curse the relationship or subject Connie to the "Wife Number Six" labels from the press. They had a daughter, Bella, in 2004 and just lived their lives.
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They finally tied the knot in 2014. It was a private, quiet ceremony at their home in Los Angeles. No vials of blood. No red carpet circus. Just a couple who had already been together for a decade deciding to make it official for their daughter.
Why Connie Angland Stuck
Why did this one work when the others didn't? Thornton has been pretty candid about this. He’s mentioned in interviews—most recently on The Drew Barrymore Show—that Connie "drug him out of the gutter."
- She isn't a "star." Connie worked in the industry as a makeup and special effects artist (Men in Black, Planet of the Apes), but she doesn't crave the spotlight.
- They’re homebodies. Billy Bob has admitted he feels uncomfortable around "rich and important people." Connie seems to share that low-key vibe.
- The Studio Factor. They even moved to a house in Pacoima because it had a recording studio, which Connie encouraged so he could work on his music without leaving home.
It's a far cry from the Hollywood lifestyle most people associate with him.
The Ghosting of Laura Dern and the Jolie Haze
You can’t talk about billy bob thornton dating without addressing the elephant in the room. Or rather, the two elephants. Before Connie, there was the infamous overlap between Laura Dern and Angelina Jolie.
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In 1999, Laura Dern was engaged to Billy Bob. She went away to film a movie, and while she was gone, her fiancé married Angelina Jolie. She famously said it was like she left the house and by the time she got back, he was married and she never heard from him again. It’s one of those legendary Hollywood "ghosting" stories that still makes people cringe.
Then came the Jolie years. It was three years of pure intensity. They were 20 years apart in age. They did the blood necklaces (which Billy Bob later clarified were just lockets with a single drop of blood, not like a beverage). They were obsessed with each other until, suddenly, they weren't.
Thornton later explained that they just had different lifestyles. She wanted to travel the world and save it; he wanted to stay home and watch baseball or play music. They’re still "very, very close friends" today, but they were never meant to last.
Every Marriage Before the Fame
Most people forget that Billy Bob was married four times before he ever met Angelina.
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- Melissa Lee Gatlin (1978–1980): His first wife back in Arkansas. They have a daughter, Amanda.
- Toni Lawrence (1986–1988): An actress he married after moving to LA to chase the dream.
- Cynda Williams (1990–1992): She starred in his breakout writing project, One False Move.
- Pietra Dawn Cherniak (1993–1997): A former Playboy model with whom he shares two sons, William and Harry.
That's a lot of life lived before he became a household name. He’s joked that some of those early marriages were just the result of "having a little too much to drink" and someone suggesting it.
Is There Trouble in Paradise in 2026?
Recently, some tabloids have tried to stir the pot. There have been claims that his ongoing friendship with Angelina Jolie is causing "friction" with Connie. An insider allegedly told Radar Online that Connie was "reeling with anger" because Billy Bob talks to Angie "all the time."
Take that with a massive grain of salt. These rumors pop up every time Thornton mentions Jolie in an interview. The fact is, he and Connie have outlasted every single one of his previous relationships combined. They were seen together at the Landman premiere late in 2024 and looked as solid as ever.
Actionable Insights for Fans
If you’re following the billy bob thornton dating saga, there are a few things to keep in mind to separate fact from tabloid fiction:
- Look at the Timeline: He hasn't been "dating" in the traditional sense since 2003. He’s been in a committed relationship/marriage for 23 years.
- Ignore the "Blood" Tropes: Most of the "weird" stories you hear are from a three-year window over two decades ago.
- Watch the Red Carpets: Connie rarely does them. If she shows up, it's a big deal and usually a sign they are doing just fine.
The real story of Billy Bob Thornton isn't about a serial groom. It's about a guy who spent the first half of his life looking for a specific kind of peace and finally found it with a special effects artist who preferred staying home over hitting the parties.
For the most accurate updates on his current life, stick to his direct interviews on shows like Jimmy Kimmel Live! or The Drew Barrymore Show, where he’s been surprisingly open about his past mistakes and his current stability.