Sylvester Stallone Admits He Was a ‘Coward’ for Breaking Up With Jennifer Flavin in a 6-Page FedEx Letter

In the landscape of Hollywood romances, few stories are as dramatic — or as redemptive — as that of Sylvester Stallone and Jennifer Flavin. The couple, now more than three decades into their relationship, survived a breakup so abrupt and impersonal that Stallone himself has since branded it “cowardly.”

The split happened in 1994, six years into their courtship. Stallone, then in his late 40s, ended things with the 26-year-old model via a six-page handwritten letter, delivered by FedEx. Reflecting on the moment during the December 3, 2024, debut episode of Sean on Fox Nation, the now 78-year-old actor didn’t mince words: “You put it down in words ’cause you don’t have the guts to do it face to face. That’s the most insincere breakup you can get.”

Flavin, in a 1994 interview with People, had recalled the shock and hurt of receiving the letter. “It was pretty sloppy,” she said at the time. “You can’t just write somebody off in a letter after six years.” For her, the real sting wasn’t just the breakup — it was the lack of a conversation.

The split was triggered by Stallone’s relationship with supermodel Janice Dickinson, who had told him she was pregnant with his child. Believing the claim, Stallone ended things with Flavin. DNA tests later proved he was not the father — a revelation that set the stage for reconciliation.

By 1995, the pair were back together. In 1996, they welcomed their first daughter, Sophia, and the following year, they married. Daughters Sistine (1998) and Scarlet (2002) followed.

The road hasn’t been without fresh obstacles. In August 2022, after 25 years of marriage, Flavin filed for divorce citing irreconcilable differences. The filing was later withdrawn, and the two remain together.

Stallone’s recent candor reflects a broader cultural shift in celebrity relationships, where stars are increasingly willing to own past mistakes. He spoke openly about his “abomination” of a relationship history and admitted that part of him didn’t even want the breakup to happen in 1994.

For Flavin, the lesson was clear: direct communication matters. For Stallone, the takeaway is accountability. “Facing it head-on would have been the right thing to do,” he admitted.

Key Timeline of Their Relationship

• Late 1980s: Couple begins dating

• 1994: Stallone ends relationship via FedEx letter after affair

• 1995: Reconcile after DNA tests disprove paternity claim

• 1996: Birth of Sophia

• 1997: Marriage

• 1998: Birth of Sistine

• 2002: Birth of Scarlet

• 2022: Flavin files for divorce; later reconciles with Stallone

In revisiting the FedEx breakup nearly three decades later, Stallone offers a reminder that even the most public figures are not immune to private missteps — and that reconciliation, while rare, is possible when humility and growth enter the equation.

Do you want me to also prepare a tabloid-style rewrite with a punchier headline and more emotional pull for mass readership? That would lean into the drama of the FedEx letter and the affair twist.