Stallone and Flavin met in 1988. The Rocky star was previously married twice — to Sasha Czack from 1974 to 1985 and Brigitte Nielsen from 1985 to 1987 — before he started dating the model. (He shares sons Sage and Seargeoh with his first wife.) The twosome hit their first bump in the road in 1994 when Stallone had an affair with Janice Dickinson more than five years into their romance.
“He sent me a six-page handwritten letter, in pen. It was pretty sloppy,” Flavin told People at the time about their breakup. “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.”
She continued: “It hit me like a ton of bricks. 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.”
Dickinson addressed the affair in her 2002 book, No Lifeguard On Duty. She was dating Michael Birnbaum at the time.
“Things hadn’t been going well with Michael for some time, and we split up later that week when I came clean about Stallone,” she wrote. “Sly didn’t call, as I had expected him to, and a week later I discovered I was pregnant. … I called Sly and went over to see him. We had supper and made love — he’d improved considerably since our brief debut. Then I told him I was pregnant.”
While the supermodel “felt the child was Sly’s,” she learned after Savannah was born that the actor wasn’t the father. He subsequently got back together with Flavin.
Stallone and Flavin went on to welcome daughter Sophia in 1996. They walked down the aisle one year later.
“I have had two great things happen to me in the past year: the birth of our beautiful daughter Sophia Rose and now my marriage to Jennifer, who is a great mother and I know will be a wonderful wife,” he said at the time.
The pair went on to welcome two more daughters, Sistine in 1998 and Scarlet in 2002. While they celebrated the milestone of 24 years of marriage in May 2022, the spouses hinted at trouble in paradise that summer.
“These girls are my priority ❤️ nothing else matters,” Flavin captioned a cryptic Instagram in August 2022. “The 4 of us forever🤍🙏🏻 #truth #family #forever.”
In the comments section, Sophia wrote, “You are our rock, cheerleader, and most incredible mom. We are so lucky to have you❤️ love you so much.” While Scarlet left a heart emoji, Sistine referred to their mother as the “strongest woman I know❤️.”
Days later, Stallone made waves when he covered up his tattoo of his wife with a giant image of Rocky’s dog.
“Mr. Stallone intended to refresh the tattoo image of his wife, Jennifer, however the results were unsatisfactory and, unfortunately, unfixable,” his rep said at the time. “As a result, he had to cover the original image with a tattoo of his dog from Rocky, Butkus.”
That same month, Us Weekly confirmed Flavin filed for divorce. “I love my family. We are amicably and privately addressing these personal issues,” he said in a statement at the time.
Scroll through for Stallone and Flavin’s timeline: