The Affair That Rocked Jennifer Flavin And Sylvester Stallone's Relationship

Jennifer Flavin and Sylvester Stallone have had a rollercoaster marriage. They've had more knockouts and comebacks than Rocky Bilbao, including a Fed-Ex break-up letter, an affair that nearly spelled the end of Flavin and Stallone's marriage before it even began, and a divorce filing followed by a retraction. The marriage snafu was preceded by news of a reality show, "The Family Stallone," which debuted on May 18.

Stallone and Flavin have a bigger age gap than most people think. According to ET, he was 42, and she was just 19 years old when they first locked eyes in a restaurant in 1988. The actor was already twice divorced and the dad of two sons, Sage and Seargeoh Stallone, from his first marriage to Sasha Czack. Two years after the rendezvous, they made their first public debut at an LA gala in 1990.

Four years later, Stallone famously split from Flavin via a six-page handwritten letter he had sent her. "It was pretty sloppy," she told People. "I cried a lot. 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. Flavin was left scratching her head, wondering why she'd been suddenly and unceremoniously dumped. She soon found out, though — it was because of an affair that nearly spelled the end of Jennifer Flavin and Sylvester Stallone's marriage before it even began.

"I'm not naïve 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," Flavin said a few years after she began dating Sylvester Stallone (via Hello!) "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."

Flavin was floored, though, when she received a "Dear Jennifer" letter in 1994. People reported that Sly didn't bother to inform Flavin of the actual reason for the split; she had to learn that from her modeling agency. Flavin's rep at Elite told her that Sly had been having an affair with fellow model Janice Dickinson who'd just given birth to a baby, Savannah Rodin, who the actor believed to be his child.

"It hit me like a ton of bricks," Flavin admitted. "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." US Weekly reports that after Dickinson learned the father was actually her ex-boyfriend Michael Birnbaum, Sly crawled back to Flavin with his tail between his legs. The newly reunited couple had their own daughter, Sophia Stallone, in 1996, and one year later, they said: "I do." Two more girls followed, Sistine Stallone in 1998 and Scarlet Stallone in 2002.

By the time they had their third daughter, Scarlett Stallone, in 2002, it seemed like Jennifer Flavin and Sylvester Stallone had put the tough times behind them. Not so fast, though; there was still a rocky road ahead. Flavin allegedly "blindsided" Sly when she filed for divorce in August 2022. "You couldn't think of a nicer couple ... she's been visiting him in Oklahoma City, where he's filming," a source told OK! "It sounded like everything was great."

However, TMZ reported that the writing was all on the wall — well, inked on the arm — after Sly covered a tattoo of Flavin's face with a pic of his new Rottweiler dog. According to the site, the canine had caused the marital spat in the first place, as Flavin hadn't wanted any more hounds in the house. Whatever the reason, the filing was soon retracted, and the couple was back on track.

Sly confirmed his marriage issues would be shown on his reality show, "The Family Stallone," in an interview with The Hollywood Reporter. "Of course, it's part of the show. It's the John Lennon thing: 'Life is what happens when you're making other plans,'" he said. "Hopefully, you're involved with people who understand the foibles of life and the fragility of it and how rare a real good relationship is. Sometimes I put the work ahead of [my family], and that is a tragic mistake which won't happen again."