Sylvester Stallone Confesses One of His ‘Regrets’ About His Marriage to Jennifer Flavin

Sylvester Stallone expressed his regrets about his 29-year marriage to former model Jennifer Flavin in a new interview with CBS Sunday Morning on 92NY.

According to many media outlets, in an interview on September 27, 80-year-old Stallone admitted, “I wish I had married my wife about eight years ago.” “I was so stupid, I was procrastinating. Because, you know, I’m actually still learning all that bad stuff about relationships.”

The “Rocky” star made the comment about Flavin, 58, after host Tracy Smith asked him if he wanted to make a “change” in his life.

“So I’m sorry. And I’m sorry, baby,” Stallone added.

Stallone said he “will never be as good as Flavin” and continued: “He’s amazing, he kept me alive.”

“And it took me so long to turn my head and say: ‘Oh, you’ve got the greatest talent in the world and you’re looking over there, you idiot!'” he continued.

Flavin and Stallone’s romance first began in 1988 when they met by chance at a restaurant in West Hollywood, California. At the time, Stallone was 42 years old and Flavin was 19 years old. The couple, who share daughters Sophia, Sistine and Scarlet, later married in 1997.

Stallone and Flavin’s marriage hit a short-term strain after Stallone filed for divorce in August 2022. They reconciled a month later.

Jennifer Flavin and Sylvester Stallone are seen in Midtown on September 13, 2026 in New York City.

TheStewartofNY via Getty Images

Before marrying Flavin, Stallone was married to Brigitte Nielsen from 1985 to 1987 and to Sasha Czack from 1974 to 1985.

Stallone credited Flavin for teaching him to love.

“It’s a habit, you know, learning to love, it’s a really great habit,” he said. “Together with my wife, Jennifer, this goal has finally come to fruition. It took nearly 60 years, but we got there.”

In a May 2023 episode of the reality TV show “The Family Stallone,” Stallone recalled what it felt like to encounter Flavin decades ago.

“I remember very clearly the first time I met Jennifer,” Stallone said. “I was in this dark restaurant with a few people. He walked in and, wow! Something happened. I felt a jolt like, ‘Oh, did we just have a little earthquake or something?'”

Flavin likewise shared, “We got along so well, it was crazy. We were inseparable all night.”

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