Sylvester Stallone Admits Regret Over Breaking Up with Jennifer Flavin via FedEx in 1994: ‘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.”

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 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.

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.

“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.”

Stallone later revealed that prioritizing his career nearly cost him his marriage to Flavin.

“Sometimes I put the work ahead of [my family], and that is a tragic mistake which won’t happen again,” he told The Hollywood Reporter.

He sang a similar tune while speaking to the Sunday Times, telling the outlet that he learned a “hard lesson” about work-life balance.

“There was a reawakening of what was more valuable than anything, which is my love for my family,” he said. “It takes precedence over my work.”