Sylvester Stallone was turned into a family man by wife Jennifer Flavin, with whom he's been with for over 30 years, out of which they've been married for 22. But the relationship wasn't always smooth sailing.
Editor's note: This article was originally published on June 18, 2021. It has since been updated.
Very few of the longest-lasting couples in Hollywood have had smooth sailing throughout their relationship. Sylvester Stallone is one man who the entire world knows about. His fame made him attractive to many women over the years but the woman who finally captured his heart transformed him into a family man. When they met, he was a famous and established actor but she was only starting out as a model.
He was known for his roving eye and two divorces at the age of 42, while she was a 19-year-old model starting out. The couple has been through many challenges in their three-decades-long history, of which they have been married for more than 23 years. They have three daughters together, who are models, and Jennifer is an entrepreneur. In 2016, Sylvester earned his third Oscar nomination for Supporting Actor in the film Creed continuing the character of Rocky Balboa, and Jennifer stood by his side.
Just like Rocky was a comeback story, so was his story with Jennifer. When they met in 1988 in a random encounter in a West Hollywood restaurant, he had had very publicly failed relationships. The two divorces had left him “battered,” “scarred,” trashed,” and “humiliated”, according to People Archives. The couple that is now going strong did not have a solid foundation to start with. They dated for nine years on and off before finally sealing the deal.
She had been there for him through the ups and downs in his career since they met and he would be there cheering for her at her shows. The relationship was not a conventional one but they had someone they could come home to.
“When we come together, it is wonderful,” Stallone said in 1991. “When we are separate, there are no strings attached. That’s the way it is. No strings.” A year later, Jennifer said, "I’m not naive about what may go on when I’m not around—he’s a 45-year-old man—I can’t change the way he is. Still. He’s not a cheating dog every day of the week. We spend five out of seven nights together, so I don’t know where he’d find the time.”
But he found the time. In 1994, he dumped her by sending a six-page letter via FedEx. “He sent me a six-page handwritten letter, in pen,” she says. “It was pretty sloppy.” He had gotten close to model Janice Dickinson, so he parted ways with Jennifer. This despite saying that “I’m loving life again" three years after he started dating Jennifer. He told the Toronto Star, according to People Archives, “Jennifer has made all the difference.” The year they spent apart was full of strings of failed relationships again.
But, just like all bad things pass, this too did pass. The couple was together by 1995 and married in 1997.
Recently, the Stallone patriarch talked about living in a house with four women. “I basically just keep my mouth shut and don’t cause waves,” he said on the Ellen Degeneres Show in 2016, according to People. “Again, she’s fantastic, but it’s all women. Women rule. Even the dogs, they’re female and the one male’s been neutered.”
He swears by his wife now. In a 2010 interview with the Daily Telegraph (via Sun UK), Sylvester said, "But I’ve never had more fun. I learned that from my wife… It took me 19 years to realize she’s always right. I realized that women have a knack, at least Jennifer, for making incredibly erudite, wise, smart decisions. I always leap without looking."
In the 1990s, when they were only dating, they spent most of their time home cooking, watching a movie, playing with the dog, walking on the beach or he would spend time at her family home in the San Fernando Valley. Her mom and sister would be there to have family time with the couple. More than 30 years later, the routine is still similar when they are not working.
In 2018, when Flavin turned 50, the entire family including daughters Sophia, Sistine, and Scarlet had stepped out to celebrate her birthday in August, according to People. They continue to share milestones even after so many years of a marriage that saw a rocky start. She was the rock that Rocky needed in his life to settle down and enjoy the smaller and precious moments of life.