A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (2025)

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A Stylish Duo Young Love Bring the Color Fancy Date Night Off to the Races Casual Day Out For a Cause Party Animals Vacay Ready Showing Support

The couple, who first met in 1988, got married on May 17, 1992

ByStephanie Sengwe

Published on May 17, 2025 08:30AM EDT

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A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (1)

Sylvester Stallone and Jennifer Flavin's love story goes way back.

The pair first met by chance while dining at a West Hollywood restaurant in 1988 and sparks immediately flew.

“I remember vividly the first time I met Jennifer,” Stallone said during an episode of their reality TV show,The Family Stallone. “I was in this dark restaurant, a few people. She came in and,whoa!Something happened. I just felt, like, this jolt, like — 'Oh, did we just have a minor earthquake or something?'"

The feeling was mutual, as Flavin confessed, "We just hit it off, it was crazy. We were inseparable all night.”

However, their 37-year relationship hasn't been without its ups and downs. The couple went their separate ways in 1994, before reconciling and getting married in 1997. Twenty-five years into their union, Flavinfiled a petition "for dissolution of marriage and other relief"from Stallone on Aug. 19, 2022. However, a month later, they called off their divorce and had their family back together.

"Let's just say that it was a very tumultuous time," Stallone told the Sunday Times. "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."

As the couple celebrates 28 years of marriage, here's a look back at Sylvester Stallone and Jennifer Flavin's early years.

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A Stylish Duo

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (2)

Stallone and Flavin complement each other in more ways than one. Above, the stylish duo is photographed in coordinated looks as they step out of the Regency Hotel in New Yorkin 1989.

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Young Love

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (3)

Months after their meeting, the two looked to be in high spirits as they were pictured at Spago in West Hollywood in 1988.

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Bring the Color

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (4)

The cheerful couple brought some color to the streets in this photo from 1989.

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Fancy Date Night

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (5)

Clearly, Spago was a favorite. Stallone and Flavin wore their date-night best as they were pictured leaving the restaurant.

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Off to the Races

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (6)

Sporting darker hair, Jennifer Flavin looked ultra-stylish next to her beau as they hit up the Santa Barbara Polo Club.

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Casual Day Out

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (7)

Even while just out and about casually, this duo were showstoppers. The couple rocked matching denim while out in Sunset Plaza in 1991.

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For a Cause

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (8)

Jennifer and Sylvester wore shades of blue at Donna Karan's Fall Collection Fashion Show to Benefit AIDS Project Los Angeles in Sept. 1992.

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Party Animals

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (9)

The two are seen having a good time at the grand opening bash for Planet Hollywood in New York City.

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Vacay Ready

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (10)

The couple took a casual stroll on the beach while vacationing in St. Tropez.

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Showing Support

A Look at Sylvester Stallone and Jennifer Flavin's Early Years as the Long-Term Couple Marks Their 28th Wedding Anniversary (11)

In 1999, the lovebirds looked chic as ever as they attended the premiere of Deep Blue Sea.