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Sylvester Stallone and Jennifer Flavin’s Relationship Timeline: All of the Highs and Lows

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Sep 6, 2024 9:03 am·

By Mike Hammer

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Sylvester Stallone has been married to Jennifer Flavin since May 17, 1997, but their longtime relationship hasn’t always been easy.

In fact, the model and entrepreneur filed for divorce from the Rocky star in August 2022 after 25 years together. However, she called off the divorce just one month later.

Their relationship history dates back to 1988, when they first met at a restaurant in Beverly Hills, California. Closer takes a look back at the couple’s longtime love.

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1988

Sylvester and Jennifer met in the late 1980s when she was just a 19-year-old Valley Girl visiting Hollywood with one of her friends, according to a 1994 People magazine story about their relationship. The two had a chance encounter at a West Hollywood restaurant. Sly was in his early 40s at the time, and he had already been married twice and had two sons, Sage (who died of coronary artery disease in 2012 at age 36) and Seargeoh, with his first wife, Sasha Czack.

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June 1990

The two made their first public appearance as a couple when they attended a Los Angeles gala in 1990. Sly looked sharp in a tuxedo with Jennifer on his arm in a chic black gown and long, sparkling earrings.

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March 14, 1994

The couple went through their first breakup almost six years after they met. According to the 1994 People story, the actor ended things by sending her a handwritten letter. “He sent me a six-page handwritten letter, in pen,” she explained. “It was pretty sloppy.” Jennifer later learned that he was having an affair with model Janice Dickinson, who gave birth to a baby in February of that year. A paternity test revealed that Sly was not the father of Janice’s daughter, and their affair came to an end.

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Sylvester Stallone with his partner Jennifer Flavin

1995

Sylvester then moved on with model Angie Everhart, whom he was briefly engaged to in 1995, according to a 1995 People magazine story. After Sly broke things off with Angie, he got back together with Jennifer.

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Sylvester Stallone with his wife Jenni fer Flavin and daughter Sophia

August 27, 1996

In 1996, Sylvester and Jennifer expanded their family by welcoming their first child together, daughter Sophia Rose.

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Sylvester Stallone with his wife Jennifer Flavin

May 17, 1997

The following year, the couple finally tied the knot. They wed in a civil ceremony at The Dorchester Hotel in London, followed by a chapel ceremony at Blenheim Palace in Oxfordshire. According to People, Jennifer’s brother Patrick revealed, “[Jennifer] said, ‘I’m on cloud nine. I couldn’t be happier.’ She said, ‘Sylvester is just beaming.'”

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USA - "Rambo" World Premiere in Las Vegas

June 27, 1998

Shortly after celebrating their first wedding anniversary, the couple welcomed their second child together, daughter Sistine Rose. Now an actress, Sistine made her film debut in 2019’s 47 Meters Down: Uncaged, also starring John Corbett.

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Jennifer Flavin (wife of Sylvester Stallone) and her daughter Scarlet

May 25, 2002

In 2002, Sylvester and Jennifer decided to add to their brood once more. They welcomed daughter Scarlet Rose. These days, she is also acting and appeared in five episodes of Tulsa King, which stars her father.

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August 19, 2022

There appeared to be trouble in paradise for Sly and Jennifer when he was seen covering up a tattoo of her face and replacing it with one of his dog Butkus, the pup from the actor’s legendary Rocky movies. At the time, Closer exclusively confirmed that the couple called it quits after 25 years of marriage. Jennifer filed for divorce in Palm Beach County, Florida, saying in court docs that “the marriage between the parties is irretrievably broken.” Sylvester said in a statement via his rep, “I love my family. We are amicably and privately addressing these personal issues.”

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September 23, 2022

One month later, the couple changed course and decided to reconcile. At the time, Sly’s rep told Page Six, “They decided to meet back up at home, where they talked and were able to work out their differences. They are both extremely happy.”

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Sophia Rose Stallone, Jennifer Flavin, Sylvester Stallone, Scarlet Rose Stallone and Sistine Stallone

May 17, 2023

The family’s reality television show, The Family Stallone — starring the three-time Oscar nominee, his wife and their daughters, Sophia, Sistine and Scarlet — officially premiered on May 17, 2023. Their family drama, including why Jennifer filed for divorce, played out for the cameras. “Of course it’s part of the show,” Sly told The Hollywood Reporter. “It’s the John Lennon thing: ‘Life is what happens when you’re making other plans.’ Hopefully, you’re involved with people who understand the foibles of life and the fragility of it and how rare a real good relationship is.”

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May 17, 2024

In honor of their 27th wedding anniversary, Sylvester shared photos on Instagram from the couple’s 1997 wedding in London. “27 years with the love of my life,” he captioned the post. In the comments section, Jennifer wrote, “I love you. Forever us!”

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