Sylvester Stallone regrets breaking up with wife Jennifer Flavin in 1994 via FedEx letter: 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.”

Sylvester Stallone regrets breaking up with wife Jennifer Flavin via a FedEx letter. Fox Nation
He and Flavin appeared on Sean Hannity’s new show, “Sean,” on Tuesday. Fox Nation

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 admitted sending his wife a breakup letter was cowardly. Fox Nation
“That’s the most insincere breakup you can get,” he said. Getty Images for amfAR

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.

The couple met in 1988. Getty Images
However, Stallone abruptly called things off six years later. WireImage

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.

Flavin told People in 1994 that Stallone had sent her a “sloppy” six-page letter. Ron Galella Collection via Getty Images
However, they reconciled in 1995. Getty Images

“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.”

The couple wed in 1997. Getty Images
They share three daughters. Stefanie Keenan

Related Posts

Kate Middleton’s Shocking Lifelong Transformation Amid Her Cancer Battle

Kate Middleton’s experience with cancer has deeply impacted her outlook on life, changing her perspective on family, resilience, and what truly matters. Royal expert Jennie Bond has revealed that the Princess of Wales has undergone a profound transformation …

Read more

Kate Middleton’s Unexpected Travel Confession Shocks Fans at St. Patrick’s Day Event

Princess Kate Middleton made a rare personal revelation while attending the St. Patrick’s Day Parade at Wellington Barracks, where she shared key details about her travel experiences and her children’s global adventures. As the Colonel of the Irish Guards, …

Read more

40 Minutes Ago, Ryan Reynolds and Family Announced Shocking News About Blake Lively in New Movie

In an emotional statement shared via the official account, Lively’s family wrote: “Blake has devoted her youth to the big and small screens. But now, she feels it is time to listen to her heart – and devote more time to her family, to herself, and to …

Read more

Princess Kate Breaks Down in Tears, Reveals Hidden Royal Tragedy That Has Shocked the Entire UK

Princess Kate has cried! She just made a shocking announcement that shook the entire UK: ‘My family is facing a great tragedy, and the royal family has been hiding from you that…’” 👇👇 Princess Kate’s Heart-Wrenching Announcement: The …

Read more

Prince William not ready to waste second chance with Kate Middleton

06/04/2025 – 07:51 CDT Prince William is said to be putting a lot more effort into his relationship with Princess Kate Middleton these days, according to a royal insider. Kate is now in remission from her cancer treatment and William is trying to make …

Read more

Kate Middleton’s ‘five minute’ morning beauty routine – including a no-phone rule

Despite her reputation for elegance at public events, Princess Kate‘s early-morning routine is surprisingly modest, says an ex-royal staffer. The Princess of Wales, a mother of three celebrated for her flawless…

Read more

Leave a Reply

Your email address will not be published. Required fields are marked *