Sylvester Stallone Once Broke Up with His Now-Wife Via a FedEx Letter, Now He Regrets His ‘Cowardly’ Decision
Sylvester Stallone, 78, has been married to his 56-year-old wife, Jennifer Flavin, for nearly 30 years. But they almost didn’t make it down the aisle.
On Tuesday, Dec. 3, Stallone sat down with Sean Hannity for a new series on Fox called “Sean,” where they talked about everything from the actor’s career to his love life. During this conversation, Stallone confessed the shocking reason why he once broke up with Flavin via a handwritten letter delivered by FedEx.
Hannity sparked the conversation asking, “Who FedExs a breakup letter?” Taking full accountability for his actions, Stallone said, “A coward does.”
He added, “That’s the most insincere breakup you can get. You can’t even say … you put it down in words ’cause you don’t have the guts to do it face to face.”
In March of 1994, the “Rocky” star sent a six-page breakup letter to Flavin, whom at that point he had been dating for six years. Flavin found out a few days later from her agent that the breakup was really because Stallone had been having an affair with model Janice Dickinson while dating her.
A month prior to Flavin and Stallone’s breakup, Dickinson gave birth to her daughter, which was rumored to be Stallone’s. But after doing a paternity test and finding out Dickinson’s child was not his, he ended their affair.
The “Creed” actor told Hannity he thought sending a letter to Flavin to end their romance was a better option because he didn’t think he could do it in person. He even admitted that “a part of [him] didn’t want to.”
Stallone says his upbringing shaped him to not be so great at relationships as he got older.
“In my profession — or my life, I should say — the way I’ve been structured is … my history with relationships is an abomination,” he said before later adding, “I was raised in an incredibly dysfunctional family. No love. No pat. No handshake… I got the s—t beat [out of me].”
Fans reacted to Stallone’s recollection of their breakup in the comments of Page Six’s report.
One person said, “That’s deplorable & way way worse than just being a coward!”
“Never have liked him. Just get the ick factor,” wrote another.
On People magazine’s Facebook page, a third person said, “He’s such a douche.”
Someone else said, “Glad he wised up and stayed.”
As for Flavin’s perspective of the breakup, she told People that the letter titled “Dearest Jennifer” was “pretty sloppy.”
Not only that, but when she found out that the true reason Stallone had broken up with her was because of Dickinson — a model she had worked with before — and her newborn baby, she was distraught.
“It hit me like a ton of bricks,” she said, “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.”
Over the next three years, the couple hit major milestones in their relationship. First they got back together in 1995, had their first of three daughters in 1996, and wed in 1997.
It’s not to say they never had any issues in their marriage. There was even a moment in 2022 when Flavin filed for divorce. But it was just a month later that Flavin decided to call off their split, and the two reconciled.
