Sylvester Stallone & Jennifer Flavin Relationship Timeline: Photos After News Their Divorce Is Off

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September 6, 2023 12:30PM EDT

Sylvester Stallone and Jennifer Flavin are back together! See photos of the couple and learn more about the relationship right here.

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Slyvester Stallone & Jennifer Flavin: Photos

Slyvester Stallone & Jennifer Flavin: Photos — Sylvester Stallone’s third marriage almost ended, but is back on track. The actor wed model Jennifer Flavin in 1997 and after 25 years of marriage and in Aug. 2022, it looked like things were over after she filed for divorce in Palm Beach, Florida. Sylvester’s rep Michelle Bega gave HollywoodLife this statement from the Oscar nominee at the time, saying, “I love my family. We are amicably and privately addressing these personal issues.”

Things took a happier turn just weeks later. By the end of Sep. 2022, the duo (who did not have a pre-nup) called their divorce off, with an insider telling Page Six, they were “extremely happy.”

Jennifer is the mother of Sly’s three daughters Sistine, Sophia, and Scarlet. He was previously wed to Brigitte Nielsen (m. 1985–1987) and Sasha Czack (m. 1974–1985), the mother is his two older sons.

It seems like Slyvester and Jennifer’s best days aren’t behind them. Here, the former couple appears in a glam moment during the 72nd annual Cannes Film Festival in France on May 24, 2019. They were there for a screening of his film ‘Rambo V: Last Blood’.

Ready for more photos of Sylvester and Jennifer now that their divorce is off? Click through the gallery for more.

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Sylvester Stallone and Jennifer Flavin Bask in Love

Sylvester Stallone and Jennifer Flavin Bask in Love — Love is in the air for the Hollywood star Sylvester Stallone and his wife Jennifer Flavin as they show their affection on their boat after a day of shopping in town during their European trip in Porto Cervo, Italy. He sweetly kissed her on her head.

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Sylvester Stallone and Jennifer Flavin walking in Italy

Sylvester Stallone and Jennifer Flavin walking in Italy — Sylvester Stallone and his wife Jennifer Flavin walk in Italy. They wore stylish outfits.

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Sylvester Stallone & Jennifer Flavin in a pool

Sylvester Stallone & Jennifer Flavin in a pool — Sylvester Stallone and his wife, Jennifer Flavin, packed on the PDA during a trip to Italy in Jul. 2023. The beauty rocked a blue bikini while Sly opted for a black t-shirt and swim shorts.

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Sylvester Stallone & Jennifer Flavin at ‘The Family Stallone’ TV Premiere

Sylvester Stallone & Jennifer Flavin at ‘The Family Stallone’ TV Premiere — Jennifer Flavin jokingly choked her husband Sylvester Stallone at the TV series premiere of ‘The Family Stallone’ in New York City on May 11, 2023.

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Sly Stallone with his family at the premiere of their show

Sly Stallone with his family at the premiere of their show — Sylvester Stallone, his wife Jennifer Flavin, and their three daughters pose at ‘The Family Stallone’ premiere in NYC. Sly wore a black jacket with a matching shirt and jeans.

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Sly Stallone and Jennifer Flavin celebrate ‘The Family Stallone’

Sly Stallone and Jennifer Flavin celebrate ‘The Family Stallone’ — Sylvester Stallone and Jennifer Flavin at ‘The Family Stallone’ premiere in NYC. The couple matched in black outfits.

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Sylvester Stallone & Jennifer Flavin with Sophia & Sistine At The ‘Tulsa King’ Premiere

Sylvester Stallone & Jennifer Flavin with Sophia & Sistine At The ‘Tulsa King’ Premiere — Sistine Stallone, Sylvester Stallone, Jennifer Flavin, and Sophia Stallone pose for photos on the ‘Tulsa King’ premiere red carpet in Nov. 2022. The family outing came just two months after Sylvester and Jennifer reconciled after a brief split

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Sylvester Stallone & Jennifer Flavin at the ‘Tulsa King’ Premiere

Sylvester Stallone & Jennifer Flavin at the ‘Tulsa King’ Premiere — Sylvester Stallone & Jennifer Flavin put on a united front at the premiere of his show ‘Tulsa King’ on Nov. 9, 2022. They posed for photos together and with their daughters.

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Sylvester Stallone, Jennifer Flavin & Their Daughters At The Ralph Lauren Show

Sylvester Stallone, Jennifer Flavin & Their Daughters At The Ralph Lauren Show — Sylvester Stallone and Jennifer Flavin posed for a beautiful photo with their two older daughters at the October 2022 Ralph Lauren fashion show in Pasadena. Sistine stunned in a gold dress, while her sister Sophia rocked a white gown.

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Sylvester Stallone & Jennifer Flavin At The Ralph Lauren Show

Sylvester Stallone & Jennifer Flavin At The Ralph Lauren Show — Sylvester Stallone wrapped his arm around his wife Jennifer Flavin’s waist as they posed for a photo at the October 2022 Ralph Lauren show. The actor sported a brown blazer, while his wife stunned in a deep red dress.

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Jennifer Flavin almost plants a kiss on Sylvester Stallone in NYC

Jennifer Flavin almost plants a kiss on Sylvester Stallone in NYC — Jennifer Flavin almost plants a kiss on Sylvester Stallone in Midtown Manhattan. The recently reconciled couple happily posed for a photo. At one point Sly does not seem to notice his wife Jennifer going for a kiss while the couple stepped out in New York City.

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The Marriage Is Back On

The Marriage Is Back On — Sylvester Stallone and Jennifer Flavin officially filed to dismiss their divorce on Oct. 7, per a report by ‘Page Six‘. An insider close to the couple confirmed the news and said they “are together and very happy.”

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Sylvester Stallone And His Wife Go To Dinner In NYC

Sylvester Stallone And His Wife Go To Dinner In NYC — Sylvester Stallone and his wife Jennifer Flavin leave The Polo Bar in NYC after a dinner date. The couple recently called off their divorce and decided to reconcile after 25 years of marriage.

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Sylvester Stallone & Family At The Premiere Of ‘Creed II’

Sylvester Stallone & Family At The Premiere Of ‘Creed II’ — Fighting spirit! Sylvester Stallone has wife Jennifer Flavin and daughter Sistine Rose at his side during the New York premiere of ‘Creed II’ on Nov. 14, 2018.

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Slyvester Stallone & His Family At The Premiere Of ‘Rambo V: Last Blood’

Slyvester Stallone & His Family At The Premiere Of ‘Rambo V: Last Blood’ — Sylvester Stallone looks so proud while attending the world premiere of his film ‘Rambo V: Last Blood’ during the 72nd annual Cannes Film Festival on May 24, 2019. His daughter Sistine (left) wore a beautidful bronze gown while his wife Jennifer Flavin (R) went with dark sparkles.

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Sylvester Stallone & Jennifer Flavin In Italy

Sylvester Stallone & Jennifer Flavin In Italy — Sylvester Stallone and Jennifer Flavin enjoy an outing in Rome in Sep. of 2019. They looked so happy together.

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Sistine Stallone With Her Mom & Dad In 2019

Sistine Stallone With Her Mom & Dad In 2019 — Sistine Stallone, on left, is supported by dad Sylvester Stallone and mom Jennifer Flavin during the HBO premiere of ‘Very Ralph’ on Nov. 11, 2019. It was clear Sistine had inherited her parent’s poise.

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Sylvester Stallone & Jennifer Flavin At The 2016 Academy Awards

Sylvester Stallone & Jennifer Flavin At The 2016 Academy Awards — Sylvester Stallone and Jennifer Flavin are pure elegance on the red carpet of the 88th Annual Academy Awards on Feb. 28, 2016. She wore a silky black dress with a sexy slit and he was dapper in dark blue.

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Jennifer Flavin & Sylvester Stallone Toast In 2016

Jennifer Flavin & Sylvester Stallone Toast In 2016 — ‘Creed’ star and Montecito Award recipient Sylvester Stallone toasts to the excellence in cinematic achievement at the Hennessy Paradis Imperial Lounge during the 31st Santa Barbara International Film Festival. Behind him was actor Carl Weathers and wife Jennifer Flavin.

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The Stallones At The 2016 Golden Globes

The Stallones At The 2016 Golden Globes — Sylvester Stallone, second from right, poses in the press room with the award for best performance by an actor in a supporting role in any motion picture for Creed at the 2016 Golden Globes. He was with (right to left) daughter Sophia Stallone, daughter Scarlet Stallone, wife Jennifer Flavin, and daughter Sistine Stallone.

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Jennifer Flavin & Sylvester Stallone In 2015

Jennifer Flavin & Sylvester Stallone In 2015 — Jennifer Flavin and Sylvester Stallone attend the premiere of the film ‘The 33’ during 2015’s AFI Fes in Los Angeles. He was casual in jeans and a jacket while she went with a blue dress.

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Sylvester Stallone & Wife In France

Sylvester Stallone & Wife In France — Sylvester Stallone and wife Jennifer Flavin Stallone enjoy some yacht time in the South of France on Jul. 26, 2014. Talk about fun in the sun!

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Sylvester Stallone & Jennifer Flavin At The Premiere Of ‘Grudge Match’

Sylvester Stallone & Jennifer Flavin At The Premiere Of ‘Grudge Match’ — Sylvester Stallone and Jennifer Flavin get cute during the premiere of ‘Grudge Match’ on Dec. 16, 2013. She looked great, donning a forest green dress while wrapping her arms around her love.

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The Stallones At The London Premiere Of ‘The Expendables 2’

The Stallones At The London Premiere Of ‘The Expendables 2’ — They’re back! Sylvester Stallone takes his wife Jennifer Flavin and their three daughters Sophia, Sistine, and Scarlet to the London premiere of ‘The Expendables 2’ on Aug. 13, 2012.

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Sylvester Stallone & Jennifer Flavin At The AFI Film Festival 2010

Sylvester Stallone & Jennifer Flavin At The AFI Film Festival 2010 — Sylvester Stallone and Jennifer Flavin attend the closing night of AFI Film Festival 2010 on Nov. 11. The gala included the world premiere of ‘Black Swan’.

Sly shared a gushing tribute to his wife while marking their 25th wedding anniversary just months before the split. Taking to Instagram, he shared, ‘There is not enough words to describe what this incredibly selfless dedicated, patient, woman has meant to our lives and I only wish they could be another 25! Thank you sweetheart!’

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The Stallone Family At The Premiere Of ‘The Expendables’

The Stallone Family At The Premiere Of ‘The Expendables’ — Family outing! Sylvester Stallone and Jennifer Flavin take their girls Sophia Rose, Scarlet Rose and Sistine Rose at the premiere of his film ‘The Expendables’. They were all dressed to the nines.

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Sylvester Stallone & Jennifer Flavin In 2010

Sylvester Stallone & Jennifer Flavin In 2010 — Sylvester Stallone and Jennifer Flavin look glam during the premiere of ‘Iron Man 2’ in LA on Apr. 26, 2010. He wore tinted shades and she was elegant in all black.

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Sylvester Stallone & Jennifer Flavin In 1999

Sylvester Stallone & Jennifer Flavin In 1999 — Sylvester Stallone and Jennifer Flavin attend the world premiere of ‘Empire of the Sun’ on July 26, 1999. They were thrilled for date night at the movies.

The couple made their first red carpet appearance together in 1990 but Sly brutally broke up with the model via a FedEx letter in 1994. They reunited not long after, and welcomed daughter Sophia in 1996.

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Sylvester Stallone & Jennifer Flavin In 1997

Sylvester Stallone & Jennifer Flavin In 1997 — Sylvester Stallone & Jennifer Flavin appear at the 1997 premiere of ‘Contact’. He gave the cameras a little look.

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Sylvester Stallone & Jennifer Flavin In 1991

Sylvester Stallone & Jennifer Flavin In 1991 — Sylvester Stallone and Jennifer Flavin appear at the L.A. Free Clinic Gala on December 11, 1991. They looked so cozy.

The duo first met in 1988 and dated on and off during the 90s. They made things official in 1997 when they were hitched at The Dorchester Hotel in London.

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