Sylvester Stallone admits he was a ‘coward’ for sending breakup letter to Jennifer Flavin via FedEx

LOS ANGELES, CALIFORNIA: We've all watched our share of Hollywood love stories, but Sylvester Stallone and Jennifer Flavin’s romance could give any movie plot a run for its money.

The 'Rocky' star recently opened up about one of the most “cowardly” moves of his life—breaking up with Flavin via FedEx. Stallone sat down with Sean Hannity on the premiere episode of 'Sean' on December 3, Tuesday, and spilled all the tea about that infamous 1994 letter, his regrets, and how their love ultimately triumphed.

Sylvester Stallone's FedEx fumble

Picture this: It’s 1994, and Sylvester Stallone — then six years into his relationship with Jennifer Flavin — decides to break things off.

But instead of having the hard conversation face-to-face, he opts for a six-page handwritten letter delivered via FedEx. Yes, the man behind 'Rambo' and 'Rocky' couldn’t muster up the courage to break up in person.

“That’s the most insincere breakup you can get,” Stallone admitted during the interview, calling himself a “coward.” He didn’t hold back on criticizing himself, adding, “You put it down in words ’cause you don’t have the guts to do it face to face.”

Why didn’t he just have the talk in person? Stallone admitted there was a part of him that didn’t actually want the breakup, per People.

“A part of me didn’t want to,” he confessed, blaming his “abomination” of a relationship history for his poor judgment.

Flavin, now 56, wasn’t exactly impressed by the FedEx stunt. Back in 1994, she opened up to People about the breakup. "He sent me a six-page handwritten letter, in pen. It was pretty sloppy," she said at the time.

"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."

The plot thickened when Flavin learned the reason behind the breakup: Stallone had been having an affair with supermodel Janice Dickinson.

Despite the messy split, fate (and perhaps some heartfelt apologies) brought the two back together. By 1995, Stallone and Flavin had reconciled, and in 1997 they tied the knot in a stunning London wedding.

Over the years, they built a life together — raising three daughters Sophia, Scarlet and Sistine Stallone. Stallone even gushed to Hannity about how much Flavin means to him, “I mean I couldn’t live without her. I mean she is my everything. My sun and my moon. Everything.”

The 2022 divorce drama

But like any great love story, theirs wasn’t without its challenges. After 25 years of marriage, Jennifer Flavin filed for divorce in August 2022. A source told People at the time that they had "been unhappy for quite some time," and that the couple "had lots of issues for years and she just had enough".

For Stallone, the thought of losing Flavin for good was a wake-up call. A source revealed he “never wanted a divorce” and had been “working hard to win her back” after the filing.

And it worked! Just one month later, the couple reconciled, with a rep for Stallone confirming that they had “talked and were able to work out their differences".

“They love each other,” a source close to Flavin added. “They want to keep their family together.”

Two years after the near-divorce, Stallone and Flavin are proving that true love can weather any storm. In May this year, Stallone marked their 27th wedding anniversary with a romantic Instagram post featuring throwback photos from their 1997 wedding.

“27 years with the love of my life,” he captioned the post. Flavin sweetly replied in the comments, “I love you. Forever us!”