Sex & relationships

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.

August 24, 2022, 11:37AM 2 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

FREZZA LA FATA – COBRA TEAM / BA

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.

July 15, 2023, 12:36PM 3 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

FREZZA LA FATA – COBRA TEAM / BA

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

July 15, 2023, 12:36PM 4 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.

July 14, 2023, 7:28PM 5 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Erik Pendzich/Shutterstock

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.

September 6, 2023, 11:50AM

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Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Stephen Lovekin/Shutterstock

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.

May 12, 2023, 8:47AM 7 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Erik Pendzich/Shutterstock

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

May 12, 2023, 8:47AM 8 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Stephen Lovekin/Shutterstock

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

November 10, 2022, 7:47AM 9 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Charles Sykes/Invision/AP/Shutte

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.

November 10, 2022, 7:47AM 10 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Chris Pizzello/Invision/AP/Shutt

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.

October 14, 2022, 8:33AM 11 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Chris Pizzello/Invision/AP/Shutt

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.

October 14, 2022, 8:33AM 12 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

BrosNYC / BACKGRID

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.

October 8, 2022, 11:38AM 13 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.”

October 7, 2022, 5:07PM 14 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.

October 7, 2022, 7:52AM 15 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Andy Kropa/Invision/AP/Shutterst

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.

August 24, 2022, 11:37AM 16 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

IAN LANGSDON/EPA-EFE/Shutterstoc

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.

August 24, 2022, 11:37AM 17 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Vincenzo Landi/IPA/Shutterstock

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

August 24, 2022, 11:37AM 18 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Mark Von Holden/Invision/AP/Shut

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.

August 24, 2022, 11:37AM 19 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.

August 24, 2022, 11:37AM 20 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Richard Shotwell/Invision/AP/Shu

‘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.

August 24, 2022, 11:37AM 21 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Jordan Strauss/Invision/AP/Shutt

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.

August 24, 2022, 11:37AM 22 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Jim Smeal/Shutterstock

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.

August 24, 2022, 11:37AM 23 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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!

August 24, 2022, 11:37AM 24 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.

August 24, 2022, 11:37AM 25 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.

August 24, 2022, 11:37AM 26 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Matt Baron/BEI/Shutterstock

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!’

August 24, 2022, 11:37AM 27 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Chris Pizzello/AP/Shutterstock

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.

August 24, 2022, 11:37AM 28 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

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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.

August 24, 2022, 11:37AM 29 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Bei/Shutterstock

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.

August 24, 2022, 11:37AM 30 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Joyce Silverstein/Shutterstock

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

August 24, 2022, 11:37AM 31 of 31

Sylvester Stallone & Jennifer Flavin Romance Timeline: Photos

Bei/Shutterstock

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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