Sylvester Stallone Says He Was a ‘Coward’ for FedExing Breakup Letter to Jennifer Flavin While They Were Dating

“That’s the most insincere breakup you can get,” Stallone admitted of the 1994 letter he sent to his future wife, saying that he eventually realized he “couldn’t live without her”

Sylvester Stallone is addressing his questionable attempt at breaking up with future wife Jennifer Flavin in a 1994 letter that he sent via FedEx.

Stallone, 78, and Flavin, 56, sat down with Sean Hannity for the inaugural Dec. 3 episode of Fox Nation’s new long-form interview show, Sean, during which the Rocky star confirmed that he did indeed send Flavin a breakup letter after they had dated for six years.

“That’s the most insincere breakup you can get,” he admitted, calling himself a “coward” for not speaking his feelings out loud. “You put it down in words ‘cause you don’t have the guts to do it face to face.”

Stallone went on to say that he thinks he avoided having the hard conversation in person at the time because “a part of me didn’t want to” split up. He further attributed the lapse in judgment to his “history with relationships,” which he described as “an abomination.”

Despite the rocky period, Stallone told Hannity, 62, that he eventually saw the light: “I mean I couldn’t live without her. I mean she is my everything. My sun and my moon. Everything.”

Actor Sylvester Stallone and wife Jennifer Flavin attend the 2016 LACMA Art + Film gala at LACMA on October 29, 2016 in Los Angeles, California
Actor Sylvester Stallone and wife Jennifer Flavin attend the 2016 LACMA Art + Film gala at LACMA on October 29, 2016 in Los Angeles, California.Jason LaVeris/FilmMagic

Flavin previously revealed how the breakup happened in a 1994 interview with PEOPLE.

“He sent me a six-page handwritten letter, in pen. It was pretty sloppy,” she said at the time. “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.”

Flavin did not know the reason for the breakup when she first received the letter, but eventually learned that it was because he had been having an affair with supermodel Janice Dickinson.

However, the pair got back together the following year and they eventually wed in 1997.

After 25 years of marriage, Flavin filed for divorce in August 2022 in a Florida court. An insider told PEOPLE at the time that the couple had “been unhappy for quite some time,” and that the couple “had lots of issues for years and she just had enough.”

The couple reconciled just one month after she filed for divorce, with a source telling PEOPLE that “they just decided to reverse course and try again.”

A rep for Stallone also told Page Six that the pair “decided to meet back up at home, where they talked and were able to work out their differences. They are both extremely happy.”

A source close to the former model also shared that Stallone “never wanted a divorce” and had “been working hard to win her back” in the months following the filing. “They love each other,” the source added. “They want to keep their family together.”

Two years after their brief divorce talk, the pair are still going strong. In May 2024, the Rambo actor paid tribute to their 27th wedding anniversary on Instagram with photos from their 1997 wedding in London.

“27 years with the love of my life,” he captioned the post. In the comments, Flavin wrote: “I love you. Forever us!”

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