Sylvester Stallone Put Himself On Blast For The Cold Way He Once Broke Up With Jennifer Flavin

Plenty of people have horror stories about being broken up with over the phone, text message, or even email. However, model Jennifer Flavin may be one of the only people who can say she's been broken up with via a FedEx letter. And even the man who sent that letter, "Rocky" star Sylvester Stallone, admits it probably wasn't the best move.

Stallone and Flavin have a massive age gap between them. They first met in 1988, when Stallone was 42 and Flavin was 19. The pair began dating shortly after, and went public with their relationship in 1990. Stallone broke things off in 1994 after he cheated on Flavin with model Janice Dickinson, and believed he had gotten Dickinson pregnant. He confessed to his infidelity in a six-page, hand-written letter, which he FedExed to Flavin. During a 2024 interview with Fox News' Sean Hannity, Stallone called himself a "coward" for how he handled things. "That's the most insincere breakup you can get," the actor said (via Daily Mail). "You put it down in words 'cause you don't have the guts to do it face to face."

Flavin herself discussed the incident in a 1994 interview with People. "It hit me like a ton of bricks. ... You can't just write somebody off in a letter after six years," she said. Flavin also described Stallone's letter itself as being "pretty sloppy." However, Stallone and Flavin got back together the following year, after a DNA test proved that Dickinson's baby wasn't actually Stallone's. Stallone and Flavin eventually wed in 1997.

Twenty-five years after the pair tied the knot, Jennifer Flavin filed for divorce from Sylvester Stallone in August 2022. "While we will no longer be married, I will always cherish the more than 30-year relationship that we shared, and I know we are both committed to our beautiful daughters," Flavin told People at the time. "I ask for privacy for our family as we amicably move forward." For his part, Stallone echoed this sentiment, telling the outlet, "I love my family. We are amicably and privately addressing these personal issues." One month later, Page Six broke the news that Stallone and Flavin had chosen to call off the divorce and give their relationship another try. "They decided to meet back up at home, where they talked and were able to work out their differences," a spokesperson for the couple said at the time.

In October 2022, Stallone opened up about his near-split from Flavin in an interview with The Times. "Let's just say that it was a very tumultuous time," he said. "There was a reawakening of what was more valuable than anything, which is my love for my family. It takes precedence over my work and that was a hard lesson to learn." Stallone cites being too focused on maintaining his career as the main reason why his family life started to fall apart around him. Speaking to Entertainment Tonight in 2023, Flavin commented, "Sometimes you do have to hit bottom before getting back up again."