Sylvester Stallone dumped his partner of 6-years Jennifer Flavin by sending a "sloppy" 6-page letter via FedEx

Sylvester Stallone dumped his partner of 6-years Jennifer Flavin by sending a "sloppy" 6-page letter via FedEx

He later asked her for a second chance and the two got back together.

"Dearest Jennifer," was how the letter began, the one written by Sylvester Stallone to his longtime girlfriend, Jennifer Flavin. After having been together for nearly six years, Flavin was caught completely off-guard when she received the unexpected letter through Federal Express. Not only had he decided to break things off with her without a conversation, but he also did through a postal letter. 

"He sent me a six-page handwritten letter, in pen," Flavin told People about the incident that took place in 1994. "It was pretty sloppy." A few days after she received the letter in her post, Flavin discovered the real reason why Stallone broke up with her and the heartbreaking secret that the Rocky star chose to skip in his note. Her agent at the Elite modeling agency told her that Stallone had been having an affair with Janice Dickinson, a model and photographer. It was even reported that Dickinson gave birth to a baby girl that Stallone was believed to have fathered.

"It hit me like a ton of bricks," said Flavin. "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."

Sylvester Stallone and Jennifer Flavin. (Photo by Diane Freed. Undated.)

After nurturing dreams of becoming together, when Flavin found out about his affair and that too in a rather humiliating way, she felt "like every woman’s worst nightmare" had come true in her life.

"I cried a lot. I called all my friends. And I cleaned my apartment about five times. I had so many pictures and things to get rid of," said Flavin, who was beyond hurt by the way her partner of several years chose to end things. "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."

On the other hand, Stallone was concerned about Dickinson, whom he planned to get married to after she told him he was the father of her baby. However, a DNA test later proved that the baby belonged to Dickinson's ex-boyfriend, according to Newser.

Following this revelation, Stallone went on to briefly date another model, Andrea Wieser leading to more rumors, as reported by The Sun. However, it took him a lot of mistakes and self-introspection to realize he was being immature and selfish. Once he saw what he was doing to himself and others, he realized that Flavin was the one and asked her for a second chance. 

Sylvester Stallone and Jennifer Flavin pose for photos at the unveiling of Mike Medavoy's star on the Hollywood Walk of Fame in Hollywood, California on September 19, 2005. (Source: Getty Images | Photo by Matthew Simmons)

Flavin chose to give Stallone another chance, which she didn't regret as he lived up to her expectations. "When they got back together it seemed they knew what they wanted," said Mitch, Jennifer’s brother, according to People. "She knows that Sly is pretty much settled down. He’s getting older, too, you know." In1995, the couple got back together and they even welcomed their first daughter in 1996.

By 1997, the two of them exchanged wedding vows. "She said, ‘I’m on cloud nine. I couldn’t be happier,'" said Patrick, Flavin's older brother. "She said, 'Sylvester is just beaming.'"

In a statement, Stallone also said, "I have had two great things happen to me in the past year: the birth of our beautiful daughter Sophia Rose and now my marriage to Jennifer, who is a great mother and I know will be a wonderful wife."

Stallone and Flavin have been together for over two decades now and have raised a family together. The couple welcomed their first daughter Sophia in 1996, Sistine in 1998, and Scarlet in 2002. Stallone also had two sons from his previous relationship, Seargeoh who was born in 1979 and Sage who passed away in 2012.

Sylvester Stallone and Jennifer Flavin (C), with their daughters (L-R) Sistine Stallon, Scarlet Stallone, and Sophia Stallone at the 74th Annual Golden Globe Awards at The Beverly Hilton Hotel in Beverly Hills, California on January 8, 2017. (Photo by Frazer Harrison/Getty Images)

After many years of family life, Flavin, now 51, and Stallone, now 73, continue to feel happy and content to spend their lives by each other's side.

"I've never had more fun. I learnt that from my wife… It took me 19 years to realise she’s always right," Stallone said in a 2010 interview with the Daily Telegraph, as quoted by The Sun. "I realised that women have a knack, at least Jennifer, for making incredibly erudite, wise, smart decisions. I always leap without looking."

On their 21st wedding anniversary, Flavin also wrote on Instagram, "21 years of marriage and still going strong with the love of my life."

This May 17, 2020, the couple celebrated their 23rd anniversary with another post that shows how much they are in love.


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