Sylvester Stallone Cheated On Wife Jennifer With A Model When She Was 'Going To Get Pregnant'
Sylvester Stallone and Jennifer Flavin had an on-and-off relationship for 38 years, marked by infidelity, splits, and reconciliations.
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Add BollywoodShaadis on GoogleSylvester Stallone is currently making headlines for opening up about severe, previously undisclosed personal struggles and past trauma. He candidly spoke about his bulimia diagnosis, steroid abuse, and cold and abusive upbringing in an interview with The New York Times. The 80-year-old action icon's revelations came days ahead of the September 29, 2026 release of his new memoir, The Steps.
Sylvester's troubled childhood made him a complex adult who ended up cheating on his wife, Jennifer Flavin while she was planning on getting pregnant and having kids with him. Here's all about his affair with supermodel Janice Dickinson, which led him to break up with Jennifer over a handwritten letter.
Sylvester Stallone left Jennifer Flavin as he thought model Janice Dickinson was pregnant with his child
Sylvester Stallone was in a long-term relationship with his third wife, Jennifer Flavin, that lasted on and off for almost four decades. The couple met and started dating in 1988, and after about five to six years, his heart wavered for another woman. Mesmerized by supermodel Janice Dickinson, the actor started an affair with her. He might have kept his infidelity a secret if Janice hadn't gotten pregnant while they were dating.
Both Janice and Sylvester thought the child was his, which prompted him to come clean about his affair to his then-girlfriend (now wife), Jennifer Flavin, and part ways with her. He broke up with her over a six-page handwritten letter sent via FedEx. Sharing her disappointment over the "sloppy" letter he sent her, Janice told PEOPLE, "It hit me like a ton of bricks."
Jennifer couldn't process the sudden split as, according to her, things were amicable between her and her beau, and she didn't know what went wrong. She further shared that she was planning to get pregnant and expand her family with Sylvester Stallone when she received the sudden blow. Jennifer didn't want to beg him to return to her; however, she felt she deserved a face-to-face explanation for his decision. In her words:
"I was disappointed. You can't just write somebody off in a letter after six years. It's not like I was going to try to beg him to come back to me or anything. I just wanted to talk...I had no idea this was going to happen. We talked about us having children, about when I was going to get pregnant. We were already picking names, marking down names that he liked and I liked."
Sylvester later admitted his mistake and told Fox Nation, "That's the most insincere breakup you can get." He called himself a "coward" for not having "the guts to do it face to face," as "a part of me didn't want to" split up.
Sylvester Stallone reconciled with Jennifer Flavin, got married, and fathered children with her
Sylvester reconciled with Jennifer after ending things with Janice Dickinson. They broke up after a paternity test confirmed that he was not Janice's baby daddy. He knew in his heart that he "couldn't live without" Jennifer and she was his "everything." He won her back, and after a few years of dating, they tied the knot on May 17, 1997, in a civil ceremony at The Dorchester Hotel in London, followed by a ceremony at Blenheim Palace.
A year before their wedding, Sylvester and Jennifer became parents to their first child, a daughter, Sophia Rose. A year after their marriage, the couple welcomed their second daughter, Sistine Rose, followed by the birth of their third daughter, Scarlet Rose in 2002. Two decades later, they filed for divorce in August 2022 and, a month later, withdrew the filing and reconciled. In May 2026, Sylvester and Jennifer celebrated their 29th wedding anniversary.
What are your thoughts on Sylvester Stallone and Jennifer Flavin's long-term on-and-off relationship, marked by infidelity? Let us know.
Photo courtesy: Jennifer Flavin/Instagram
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