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Sylvester Stallone Revealed the ‘Insincere’ Way He Broke up With Jennifer Flavin in Their Dating Era

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Sylvester Stallone has one of the wildest dating tales that’s a part of Hollywood gossip history. He isn’t exactly proud of how he handled the awkward moment, but he’s owning up to his mistakes decades later. 

We have to go back to the ’90s when the Rocky star was dating model Jennifer Flavin. They had been together for six years when he suddenly broke up with her via a six-page FedEx letter. Yes, you read that correctly. It was just as bad as a Sex and The City Post-it note. There’s more to the story than cold feet, though.

Janice Dickinson attends the 2018 Carousel of Hope Ball at The Beverly Hilton Hotel on October 6, 2018 in Beverly Hills, California.

Stallone had an affair with supermodel Janice Dickinson, and she got pregnant with daughter Savannah in 1994. They both believed that the actor was the father until he took a DNA test — it was a very Maury Povich moment. It turns out Dickinson’s then-boyfriend Michael Birnbaum was the dad. Oh, what a tangled web for everyone involved. 

The Tulsa Kings star admitted on Fox News on Dec. 3 that it was “the most insincere breakup you can get.” He described himself as a “coward” for not breaking up with Flavin “face-to-face” because he didn’t want to leave the relationship. “I mean, I couldn’t live without her,” Stallone added. “She is my everything. My sun and my moon. Everything.”

The unexpected DNA results allowed Stallone to reconcile with Flavin. The couple married in 1997 and share three daughters, Sophia, 28, Sistine, 26, and Scarlett, 22. Still, Flavin had some harsh words for Stallone in 1994 when the mess began. 

“It hit me like a ton of bricks,” she told People while calling his letter “pretty sloppy.” “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 added, “I was disappointed. 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 finally got that chance once paternity was established and Stallone cut ties with Dickinson, but it’s probably a journey she would have rather not have been taken on in the first place. Still, it is a part of golden Hollywood gossip.

Before you go, click here to see all the celebrity couples who have stayed together after cheating scandals.