Sylvester Stallone says he was a ‘coward’ for FedExing breakup letter to Jennifer Flavin

Sylvester Stallone says he was a “coward” for sending a breakup letter via FedEx to his now-wife Jennifer Flavin 30 years ago.

The “Rambo” actor, 78, opened up about the awkward decision during an interview with Sean Hannity on Fox Nation Tuesday, expressing regret over how he decided to end the pair’s 6-year relationship in 1994.

“That’s the most insincere breakup you can get,” he said, adding that he was a “coward” for doing that. “You put it down in words ‘cause you don’t have the guts to do it face to face.”

Sylvester Stallone and Jennifer Flavin in tuxedos circa 1995
30 years ago, Stallone sent Flavin a six-page handwritten letter to end their romance. Getty Images

The “Rocky” actor said his “history with relationships” got the better of him and avoided ending things with Flavin in person because “a part of me didn’t want to” break up.

Luckily, the pair had managed to find their way back to one another.

In 1994, Flavin told People that Stallone sent her a six-page handwritten letter to end their romance.

Sylvester Stallone and Sean Hannity sitting at a table with microphones during an interview, discussing Stallone's past relationship with Jennifer Flavin.
The “Rambo” actor, 78, expressed regret over how he decided to end the pair’s 6-year relationship in 1994. Fox Nation

“It was pretty sloppy,” Flavin said. “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.”

While she didn’t know the reason behind the breakup at the time, Flavin soon found out it was because Stallone was embroiled in an affair with supermodel Janice Dickinson.

The duo ultimately reconciled and tied the knot in 1997.

Sylvester Stallone and Jennifer Flavin standing at a podium speaking during an amfAR event in Las Vegas, Nevada
The duo ultimately reconciled and tied the knot in 1997. Getty Images for amfAR

“I mean I couldn’t live without her. I mean she is my everything. My sun and my moon. Everything,” Stallone said of his third wife, and the mother of his three daughters; Sistine, Sophia, and Scarlet.

However, in 2022, the couple suffered another bump in the road when Flavin filed for divorce from Stallone after 25 years of marriage.

After one month of divorce proceedings, the pair scrapped plans to go their separate ways — and instead reconciled.

Two years later, the couple celebrated their 27th wedding anniversary.

Sylvester Stallone, Jennifer Flavin, and their daughters Sophia, Scarlet, and Sistine posing together at A Sense Of Home's First Annual Gala in Beverly Hills, California.
The couple share three daughters together; Sistine, Sophia, and Scarlet. Getty Images for A Sense of Home

Taking to Instagram in May, Stallone posted several images from the pair’s 1997 London wedding.

“27 years with the love of my life,” he captioned the post, to which Flavin replied, “I love you️Forever us!️️️.”

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