Sylvester Stallone regrets breaking up with wife Jennifer Flavin in 1994 via FedEx letter: I’m a ‘coward’

Sylvester Stallone admitted it was cowardly to send now-wife Jennifer Flavin a breakup letter via FedEx back in 1994.

Stallone, 78, and Flavin, 56, sat down with Sean Hannity for the first episode of his new Fox Nation series, “Sean,” discussing everything from the actor’s most iconic roles to their love story and brief split.

“Who FedExs a breakup letter?” Hannity asked, to which the “Rocky” star replied, “A coward does.”

“That’s the most insincere breakup you can get,” Stallone continued. “You can’t even say… you put it down in words ‘cause you don’t have the guts to do it face to face.”

Sylvester Stallone regrets breaking up with wife Jennifer Flavin via a FedEx letter. Fox Nation
He and Flavin appeared on Sean Hannity’s new show, “Sean,” on Tuesday. Fox Nation

Stallone said he took the easier approach because he knew deep down that he “didn’t want” to break up and would have crumbled in person.

The “Rambo” actor explained that he had never experienced healthy relationships — familial or romantic — at the time, and didn’t know how to effectively communicate.

“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.

“I was raised in an incredibly dysfunctional family. No love. No pat. No handshake… I got the s—t beat [out of me].”

Stallone admitted sending his wife a breakup letter was cowardly. Fox Nation
“That’s the most insincere breakup you can get,” he said. Getty Images for amfAR

Stallone explained that his rocky upbringing helped him professionally because he understands “hardship,” “rejection” and “fear” — but it did the opposite for his love life.

Despite the odds, he was able to work things out with Flavin.

“I couldn’t live without her,” Stallone gushed. “I mean, she is my everything. My sun and my moon. Everything.”

Stallone met the then-19-year-old model in 1988 but they didn’t go public with their romance until two years later.

The couple met in 1988. Getty Images
However, Stallone abruptly called things off six years later. WireImage

However, in 1994, their relationship came to a crashing halt after Flavin received a “sloppy” “six-page handwritten letter” in the mail.

“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 told People at the time.

Although it wasn’t mentioned in the message, Flavin later discovered that Stallone had been having an affair with supermodel Janice Dickinson.

“It hit me like a ton of bricks,” she said of Stallone’s infidelity.

Flavin told People in 1994 that Stallone had sent her a “sloppy” six-page letter. Ron Galella Collection via Getty Images
However, they reconciled in 1995. Getty Images

“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.”

She ultimately gave the actor a second chance and they welcomed their first child in 1996. They tied the knot the following year.

However, after 25 years of marriage and three children together, the pair hit another hiccup.

In August 2022, Flavin filed for divorce from the “Expendables” star — only to take him back one month later.

“They decided to meet back up at home, where they talked and were able to work out their differences,” a rep for the actor told us at the time. “They are both extremely happy.”

The couple wed in 1997. Getty Images
They share three daughters. Stefanie Keenan

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