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Sylvester Stallone Once Broke Up With Jennifer Flavin By FedEx-ing Her a Breakup Letter

Photo Credit: Jim Smeal / Ron Galella Collection / Getty Images
Photo Credit: Jim Smeal / Ron Galella Collection / Getty Images

Sylvester Stallone and Jennifer Flavin have been together for as long as we can remember, but there was once a time when they’d broken things off. Actually, Stallone broke things off in a pretty impersonal way. Sitting with Sean Hannity for the first episode of Fox Nation‘s new long-form interview show, Sean, Stallone and Flavin shared how he broke up with his future wife by mailing her a letter – via FedEx!

Sylvester Stallone called his actions that of a ‘coward’

Sylvester Stallone and Jennifer Flavin standing together on a red carpet
Sylvester Stallone and Jennifer Flavin, 1994. (Photo Credit: Frank Trapper / CORBIS / Getty Images)

In the interview, Sylvester Stallone confirmed that he had, in fact, mailed Jennifer Flavin a breakup letter after six years of dating. “That’s the most insincere breakup you can get,” he admitted to Sean Hannity.

Reflecting on his actions, the actor called himself a “coward” for not speaking with Flavin and expressing his feelings directly, saying, “You put it down in words ’cause you don’t have the guts to do it face to face.”

Stallone explained that part of the reason he was unable to have the difficult conversation with his now-wife was because “a part of me didn’t want to” break things off. When stating why he did it, the actor referred to his “history with relationships,” which he called “an abomination.”

Of course, he came around and realized the mistake he’d made. The two got back together, and Stallone remains totally enamored with Flavin. “I mean I couldn’t live without her,” he gushed. “I mean she is my everything. My sun and my moon. Everything.”

Jennifer Flavin needed to know why

Sylvester Stallone walking through a crowd, with Janice Dickinson following him
Sylvester Stallone and Janice Dickinson, 1983. (Photo Credit: Thomas Iannaccone / Getty Images)

In 1994, shortly after Sylvester Stallone mailed the letter to Jennifer Flavin, she shared the experience in an interview.

“He sent me a six-page handwritten letter, in pen. It was pretty sloppy,” she explained, adding, “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.”

Originally, Flavin couldn’t understand why Stallone break things off after such a long time, but eventually the truth came to light. It turns out he’d been having an affair with supermodel Janice Dickinson.

From a rocky relationship to a strong one filled with love

Sylvester Stallone and Jennifer Flavin standing together on a red carpet
Sylvester Stallone and Jennifer Flavin, 2023. (Photo Credit: Ryan Emberley / Getty Images for Netflix)

Despite all that happened, Sylvester Stallone and Jennifer Flavin got back together the following year. Things must’ve been going well, as they tied the knot just two years later, in 1997. They then had three daughters together: Sophia, Sistine and and Scarlet.

Like every relationship, things weren’t always perfect. The couple struggled with a rocky period that resulted in Flavin filing for divorce in 2022. However, just a month later, she reversed the filing, as they worked on their problems and rekindled their love for one another.

More from us: Denzel Washington Reveals He ‘Gave Up’ on Oscars After Losing to Kevin Spacey: ‘I Got Bitter’

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Today, Sylvester Stallone and Jennifer Flavin are as strong as ever.

Samantha Franco

Samantha Franco is a Freelance Content Writer who received her Bachelor of Arts degree in history from the University of Guelph, and her Master of Arts degree in history from the University of Western Ontario. Her research focused on Victorian, medical, and epidemiological history with a focus on childhood diseases. Stepping away from her academic career, Samantha previously worked as a Heritage Researcher and now writes content for multiple sites covering an array of historical topics.

In her spare time, Samantha enjoys reading, knitting, and hanging out with her dog, Chowder!

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