Sylvester Stallone split from his wife via FedEx letter and now 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, December 3, Stallone met with Sean Hannity latest series on a Fox show called “Sean” where they talked about every part from the actor’s profession to his love life. During that conversation, Stallone revealed in a handwritten letter delivered by FedEx the shocking reason he once broke up with Flavin.

Hannity initiated the conversation by asking, “Who sends a breakup letter?” Taking full responsibility for his actions, Stallone said, “A coward does that.”

He added: “This is the most dishonest breakup you can get. You can’t even say… put it into words because you don’t have the courage to do it face to face.”

In March 1994, the “Rocky” star sent a six-page breakup letter to Flavin, whom he had been dating for six years. Just a few days later, Flavin learned from her agent that the breakup was often because Stallone was having an affair with model Janice Dickinson while he was dating her.

A month before Flavin and Stallone broke up, Dickinson gave birth to a daughter who was rumored to be Stallone’s daughter. But after taking a paternity test and checking out that Dickinson’s baby was not his, he ended their affair.

The “Creed” actor told Hannity that he thought sending a letter to Flavin to finish their romance could be a greater option because he didn’t think he could do it in person. He even admitted that “part of (him) didn’t want it.”

Stallone claims that his upbringing shaped him in order that as he got older, he didn’t do as well in relationships.

“In my profession — or I should say, in my life — I have this structure… my history with relationships is terrible,” he said, before adding: “I grew up in an incredibly dysfunctional family. No love. No pats. No handshakes…I don’t give a shit (of me).”

Fans reacted to Stallone’s recollections of their breakup within the comments of the Page Six report.

One person said: “This is deplorable and much worse than being a coward!”

“I never liked him. Just get on with it,” wrote one other.

There’s a 3rd person on People magazine’s Facebook page he said“He’s such an asshole.”

Someone else said: “I’m glad he wisened up and stayed.”

As for the prospect of Flavin breaking up, that is her he said People said the letter, titled “Dearest Jennifer,” was “pretty sloppy.”

Not only that, but when she discovered that the actual reason Stallone broke up along with her was due to Dickinson – a model she had previously worked with – and her newborn child, she was devastated.

“It hit me like a ton of bricks,” she said. “I had no idea something like this is able to occur. We talked about having children and once I was going to get pregnant. We were already selecting names, ticking off the names he liked and those I liked.

Over the subsequent three years, the couple achieved major milestones of their relationship. They first got back together in 1995, the primary of their three daughters was born in 1996, and they married in 1997.

This doesn’t suggest they never had any problems of their marriage. There was even some extent in 2022 when Flavin filed for divorce. But only a month later, Flavin decided to call off their split and they reconciled.