Reflecting on 29 years of marriage, 80-year-old actor Sylvester Stallone revealed during a live stage appearance in New York that his regret is not marrying his wife, Jennifer Flavin, eight years earlier. Stallone credited Flavin with teaching him how to love after years of struggling with relationships.
Sylvester Stallone opened up about his personal life during a live audience conversation with Tracy Smith at CBS Sunday Morning at 92NY on Monday, Sept. 28, 2026. Asked about the “do-over” he would choose if he could change any situation in his life, the actor reflected candidly on his relationship with his 58-year-old wife, Jennifer Flavin.
A Chance Encounter in 1988 and Decades Together
Stallone and Flavin first met by chance at a restaurant in 1988. After years together, the couple tied the knot in 1997 and celebrated their 29th wedding anniversary in May. Reflecting on the delay in walking down the aisle, Stallone admitted to the audience that he spent years procrastinating.
I was like such an idiot, procrastinating. Uh, so I regret that. And I’m sorry, baby.
Learning to Love and Childhood Reflections
The Tulsa King
star, who has been married three times, shared that being with Flavin ultimately taught him what love feels like. He noted that learning to love became a really wonderful habit
that finally came to fruition after about 60 years.
When Smith asked whether a lack of affection from his parents during childhood might have influenced his past relationship struggles, Stallone agreed that it played a part. He compared an infant to a pile of wet clay,
explaining that early drops leave permanent dents that do not go away through life.
Family Life and Past Turbulence
Stallone shares daughters Sophia, Sistine, and Scarlet with Flavin. He also shares sons Seargeoh and Sage—who died in July 2012—with his first wife, Sasha Czack.
The couple’s decades-long marriage has faced public challenges, including an August 2022 filing where Flavin nearly divorced the actor and alleged he engaged in the intentional waste of shared assets. Following a reconciliation a month later, Stallone acknowledged to The Hollywood Reporter that he had previously put work ahead of his family, calling it a tragic mistake.
