How many times has Sylvester Stallone been married?

We often think getting anything is an easy feat for celebrities. But when it comes to love, finding “the one” remains an elusive task even for the A-listers. Don’t believe me? Go ask Sylvester Stallone.

The Rocky star has always ridden high on the never-ending dedication and love of his fan-following which has only grown in numbers. But his love life went through many ups and downs, before finding a somewhat glitchy forever in entrepreneur and former model Jennifer Flavin. But the road to this recently bumpy ever-after took many years and three marriages including multiple affairs and two very brief engagements.

Sylvester Stallone married Sasha Czack in 1974

At the age of 28, The Expendables star married photographer Sasha Czack, having two sons — Sage Stallone (who passed away at the age of 36) and Seargeoh Stallone (as for where is now, he is living in their La Quinta estate with his family) — with her. But their rocky marriage, which hit its biggest wall when Stallone kindled an affair with Susan Anton and didn’t recover even when Sasha took him back, ended after a decade in 1985.

Sylvester Stallone next married Brigette Nielson for 19 short months

Just a few months after divorcing Sasha Czack, Stallone tied the knot with model and actress Brigette Nielson, who was formerly married to Danish musician Kasper Winding. But their marriage, described by Nielson as “horrible” in a chat with The Guardian, was even more short-lived as it reached its culmination after 19 months.

“Everybody looks at you as a villain. After I left Sylvester, I kind of felt like I was blacklisted for a long time. I am almost positive that had I not been in the public eye with this famous man, that would never have happened. But they always thought: after Stallone, who is going to be next?”

Sylvester Stallone found forever with Jennifer Flavin, but after ditching her for brief affairs

Stallone met Flavin in 1988, when she was a young Valley Girl and he was already divorced twice and the father of two sons. The attraction and initial zing were instantaneous and mutual, but after six years of solid relationship, he momentarily ditched it all in favor of having a short-lived affair with supermodel Janice Dickinson. In fact, he broke up with Flavin via a FedEx-ed letter!

“He sent me a six-page handwritten letter, in pen,” Flavin shared with People in 1994. “It was pretty sloppy.”

But after Janice gave birth to a baby girl and a DNA test debunked the rumors that Stallone was the father, he broke up with her. He was then briefly engaged to Sports Illustrated swimsuit model Angie Everhart, but even that went down in flames, leaving the actor to realize that he found his “the one” in Jennifer Flavin and voluntarily lost her.

His next decision was to fix his errors by convincing Flavin that he had learned from his mistakes. And though it took some time, she eventually forgave him despite being aware of his history of cheating in his relationships, and the two reconciled in 1995, welcoming their first daughter, Sophia Rose Stallone, in 1996, and getting married in 1997. The birth of Sistine Rose in 1998 and Scarlet Rose in 2002, followed and their marriage remained strong for 25 years… until 2022, when Flavin filed for divorce in August.

But, despite the rumors and speculations regarding the divorce, Stallone once again managed to woo her back as they reconciled by September 2022, with their divorce petition officially dismissed soon after. Judging by their latest appearances, the couple is once again going strong and still very much in love.