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Sylvester Stallone’s Dating History: Was There a Pamela Anderson Fling Before Jennifer Flavin?

Published 01/26/2023, 8:45 PM EST

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Due to its lasting influence since its premiere 46 years ago, “Rocky” is widely regarded as the best film ever made about sports by many fans of the genre. The film won the Best Picture Award at the 49th Academy Awards. In addition, it spawned four sequels every three years until 1985, followed by a fifth iteration five years later and a sixth edition 16 years later in 2006. Sylvester Stallone was a crucial part of the franchise in several capacities, including as an actor, director, and screenplay.

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As far as his personal life is concerned, Stallone has gone through three marriages. From his first marriage, he had two sons, and from his third, he gained three daughters.

However, Stallone’s relationships and dating life might generate a lot of interest among his ardent fans


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Did Sylvester Stallone and Pamela Anderson ever date?

Pamela Anderson‘s Netflix documentary, “Pamela, a love story,” premieres on January 31st; where she claims that to win her affection, Sylvester Stallone offered her luxury items such as cars and real estate but with the condition that she would be his “No. 1 girl.”

She said that Sly “offered me a condo and a Porsche to be his ‘No. 1 girl,’ “And I was like, ‘Does that mean there’s No. 2? Uh-uh,'” “


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He went on, ‘That’s the best offer you’re gonna get, honey. You’re in Hollywood now.’ … [But] I wanted to be in love. I didn’t want anything less than that.”

A representative from Stallone’s office responded, “The statement from Pamela Anderson attributed to my client is false and fabricated. Mr. Stallone confirms that he never made any portion of that statement.”

Women whom Sylvester Stallone was in a relationship with or was rumored to be in one

In December of 1974, at the age of 28, he tied the knot with Sasha Czack, a photographer. They had two kids between 1974 and 1979. Stallone left Sasha following the 1978 release of his film “Paradise Alley.” In an interview with Rolling Stone, he explained how he had fallen into a period of isolation, family resentment, and competitive envy.

Sylvester Stallone had a public romance with model-actress Susan Anton while still married to Sasha, but the two eventually broke up. He ultimately admitted to Sasha that he missed his family, and they reunited, although their marriage ended in divorce that same year, 1985.

Their firstborn, Sage Moonblood Stallone, died at age thirty-six from heart illness; Seargeoh, their younger son, was identified with autism at a young age.

After that, Stallone wed model and actress Brigitte Nielsen. Reportedly Nielsen made first contact by sending a suggestive photo of herself to Stallone’s hotel room. Still married to their respective spouses at the time, Sly and Nielsen’s marriage came about only after the divorces were finalized. The couple’s marriage survived for around 19 months.

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In 2019 Brigitte told “The Guardian,” “Everybody looks at you as a villain. After I left Sylvester, I kind of felt like I was blacklisted for a long time. I’am also positive that had I not been in the public eye with this famous man, that would never have happened. But they always thought, after Stallone, who is going to be next?”

Sylvester Stallone’s relationship with wife Jennifer Flavin

Sylvester Stallone reportedly met his third wife, model Jennifer Flavin, in 1988, when Jennifer was 19 and Stallone was 42. However, only by 1990 that the couple’s relationship details reach the public at a Los Angeles function.

In a “People” magazine interview in 1994, Flavin said that Sly had sent her a breakup letter via FedEx. But, she said, “He sent me a six-page handwritten letter in pen; it was pretty sloppy.”


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Flavin eventually learned the cause behind Sly leaving her. His new relationship with supermodel Janice Dickinson. They got back together in 1995, and in 1996 had their first child, Sophia Rose Stallone. They married a year later. The couple welcomed two daughters: Sistine Rose in 1998 and Scarlett Rose in 2002.

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Jennifer Flavin filed for divorce from Stallone after 25 years of marriage in August last year. But by October, they had mutually decided to end their separation.


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Watch Out for More: Sylvester Stallone’s Earnings From ‘Rocky’ & ‘Creed’ Movies

Which is your favorite Sylvester Stallone movie? Do share with us in the comments below.

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Written by:

Jaideep R Unnithan


One take at a time

After completing 18 years in the corporate sector, Jaideep decided to make a move out of the comfort zone and follow his heart's calling to becoming a writer. His understanding of Boxing began with Iron Mike's debut as an 18 year old in 1985. Like anyone and everyone else, he holds Muhammad Ali as the greatest, though his personal favorite remains the 'PacMan' Manny Pacquiao for his speed and sheer toughness.
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Edited by:

Arijit Saha