Sylvester Stallone recalls 'cowardly' breakup letter to wife Jennifer Flavin

Sylvester Stallone once tried to take the easy way out in a long-term relationship — and he regrets it to this day.

During the premiere episode of Sean on Fox Nation on December 3, the Hollywood star reflected on the infamous breakup letter he sent to his then-girlfriend and now-wife Jennifer Flavin via FedEx in 1994.

“That’s the most insincere breakup you can get,” Stallone, 78, admitted to host Sean Hannity. Calling himself a “coward,” Stallone added, “You put it down in words ’cause you don’t have the guts to do it face to face.”

At the time, Stallone and Flavin had been dating for six years, but the split didn’t stick. Stallone confessed that “a part of [him] didn’t want to” break up, describing his relationship history as “an abomination” before realising, “I mean, I couldn’t live without her… She is my everything. My sun and my moon. Everything.”

Flavin, now 56, previously described the incident in a 1994 interview with People magazine, recalling the Rocky star’s six-page handwritten letter. “It was pretty sloppy,” she said. “You can’t just write somebody off in a letter after six years.”

She later learned the breakup stemmed from Stallone’s affair with supermodel Janice Dickinson.

The couple reconciled the following year and married in 1997, navigating ups and downs over their 27-year union, including a brief divorce filing in 2022.

Today, their bond remains strong. In May 2024, Stallone celebrated their anniversary on Instagram, writing, “27 years with the love of my life,” while Flavin commented, “I love you. Forever us!”