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“The most insincere breakup you can get” — Sylvester Stallone

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"The most insincere breakup you can get" — Sylvester Stallone

Sylvester Stallone, the iconic star of Rocky and Rambo, is opening up about one of the most vulnerable moments of his life—a breakup letter he now regrets sending via FedEx.

In a candid interview with Fox News’ Sean Hannity on December 3, Stallone called himself a “coward” for his impersonal split from Jennifer Flavin, his partner of six years at the time.

In 1994, Sylvester Stallone and Jennifer Flavin were at a crossroads in their relationship when the actor sent a six-page letter to end things. Flavin, blindsided, later revealed to People that she learned of the breakup through the mail, alongside rumors of Stallone’s affair with model Janice Dickinson.

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Stallone now admits the decision was a mistake born from his “history with relationships” and a lack of courage. Reflecting on the incident, he told Hannity:

“That’s the most insincere breakup you can get… You put it down in words ‘cause you don’t have the guts to do it face to face.”

Despite the FedEx fallout, the pair reunited a year later and married in 1997. Their journey has been anything but smooth—marked by highs, including the birth of their three daughters, and lows, such as Flavin filing for divorce in 2022. Yet, the couple ultimately reconciled, proving that their bond could withstand even the rockiest of challenges.

This past May, Sylvester Stallone and Jennifer Flavin celebrated 27 years of marriage with their daughters Sophia, Sistine, and Scarlet by their side.

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