Obvious Signs Billy Bob Thornton And His Sixth Wife Connie Won't Last

Billy Bob Thornton has lived a very interesting life, and his relationships over the years definitely add to that. Thornton dated and got engaged to six women from the late '70s to the early 2000s, marrying five of them. His engagement with fellow actor Laura Dern in the late '90s was a very high-profile match, but he abruptly left her and married the much-younger Angelina Jolie. However, in addition to the huge age gap between Thornton and Jolie, Jolie said in a post-divorce Vanity Fair interview that they were too different, resulting in an amicable divorce in 2003.

After decades of sudden breakups and divorces, Thornton started dating his current wife Connie Angland in 2003. They had their daughter Bella a year later but didn't marry until 2014 due to some reservations on Thornton's end. He told Maxim in 2008, "I told Connie I didn't want to put her through that. We do fine. ... If we get married, then the press will start calling her 'Number Six.'" His marriage to Angland is the longest one he's had, but the relationship may have some issues that could affect whether or not it's really till death do they part.

Billy Bob Thornton considered some of his past marriages and relationships a spur of the moment decision in a 2025 interview with Rolling Stone. He said, "The other times I got married were just like, you had a little too much to drink one night and somebody said, 'We should get married.' You go, 'Yeah, OK.'" However, some dissolved due to a mix of an impulsive "I do" and infidelity.

According to People, his first wife Melissa Lee Gatlin divorced him, in part accusing him of cheating. Their daughter Amanda was only a toddler when they split. Laura Dern also implied that he cheated on her when she recalled the truth about her and Thornton's relationship with Talk magazine. "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," Dern said (via ABC News).

Studies on whether cheaters always cheat have varying results. While the likelihood of repeated infidelity depends on the couple, Thornton cheating more than once soured his reputation, and his past could reasonably create tension in his marriage to Connie Angland.

An age gap relationship isn't always a red flag, and plenty of Hollywood couples have one. Still, it might raise some eyebrows here and there, especially when a man repeatedly dates much younger women. Leonardo DiCaprio is known for his scandalous age gaps, with his girlfriend Vittoria Ceretti and ex-girlfriend Camila Morrone being more than 20 years younger than him. Some of DiCaprio's relationships from the early 2000s to the 2010s also had age gaps between 10 and 20 years.

Billy Bob Thornton and DiCaprio have seemingly had a similar path with their relationships, though Thornton has now settled down with a family. He and Connie Angland, who is reportedly nine years his junior, wed a decade after dating and raising their daughter. Thornton also has a history of dating much younger women prior to meeting Angland. His third wife Cynda Williams is 11 years younger, and Laura Dern is 12 years younger. Thornton's fourth wife Pietra Dawn Cherniak is 15 years his junior. Additionally, Angelina Jolie married Thornton at 25 when he was 45, making this age gap the largest at 20 years.

Given that Thornton's no stranger to a May-December romance, it no surprise that he settled down with Angland. But the two might face some challenges as Thornton moves through his twilight years.

After his relationship with Angelina Jolie, Billy Bob Thornton made sure to keep his love life to himself as much as possible. On "Oprah's Master Class" podcast, Thornton said he struggled with the lack of privacy during his marriage to Jolie. However, has he gone too far in the opposite direction?

Thornton and Connie Angland are not often seen in public together and only occasionally go out for Hollywood events, such as premieres for Thornton's projects or awards shows, like the 2025 Golden Globes. Devoting time to your partner as a celebrity while keeping a level of privacy isn't limited to showing up to red carpets, and doing so without any other public dates might not be the best look for the couple and could hint at trouble in paradise.

However, other celebrities have been strategic about maintaining an active but private dating life. For example, a source for Jennifer Anniston told InTouch that the actor has dates at home to avoid the paparazzi. It's possible Thornton and Angland are doing the same to keep their spark alive; the "Goliath" actor told Rolling Stone in 2025 about spending some quality time with Angland and his children for his 70th birthday, instead of frequenting Hollywood's party scene. While Thornton and Angland seem to enjoy keeping their marriage out of the limelight, it wouldn't hurt for them to hit the town together every now and then.