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Inside Sylvester Stallone's Rocky Yet Enduring Love Story With Wife Jennifer Flavin

The couple has been together over 25 years.

Sylvester Stallone may be famous for knocking out opponents in the boxing ring or fighting corrupt police officers on screen, but when the cameras are off, he's actually a huge family man. 

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In fact, the Rocky and Rambo franchise star is actually a full-on girl dad and has been married to his wife, Jennifer Flavin, for more than 25 years. And once you get past all those muscles and his intimidating stature, Stallone can be a little mushy about it all. 

The entire family of five recently debuted their personal lives and Stallone's more sensitive side on a new reality television series, The Family Stallone. During its eight-episode season, viewers were introduced to the four women behind the Academy Award-nominated actor as they work to achieve their dreams, battle through family drama and support each other. 

The Family Stallone not only was a debut for Stallone's three daughters, but it was also a sort of public debut for his wife. While she was a swimsuit model when she was younger, Flavin has largely stayed out of the spotlight during the couple's quarter of a century together. 

The duo often presents a united front on screen, but much of the public knows their journey to 25 years of love hasn't always been smooth or easy. You could say it's been a little...rocky. 

Here's everything we know about Stallone and Flavin's relationship:

An On-and-Off Love

HOLLYWOOD, CA - FEBRUARY 28: Actor Sylvester Stallone (L) and model Jennifer Flavin attend the 88th Annual Academy Awards at Hollywood & Highland Center on February 28, 2016 in Hollywood, California.

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Stallone had already been married and divorced twice when he met Flavin. 

His first marriage was with actress, photographer and writer Sasha Czack, who supported the Tulsa King star before he made it big in Hollywood. The pair were married for 11 years and had two sons together, Seargeoh and Sage. Their eldest, Sage, unfortunately died in 2012 from a heart condition. 

But the stresses of the budding star's schedule weighed heavily on the couple, and they divorced in 1985. Only months later, Stallone married his Rocky IV co-star, Brigitte Nielsen. But their romance was short-lived as they called it quits only 19 months later in 1987.

By then, Stallone was one of Hollywood's highest-paid actors and already had two Oscar nominations under his belt. It was during his peak stardom that he met Flavin. The pair first locked eyes at a restaurant in West Hollywood in 1988. At 19-years-old, she had made the trek from her home in the Valley to get dinner with a friend. 

The pair hit it off quickly, despite their 22-year age difference. They quickly clung to each other and started lighting up red carpets and other Hollywood events as a couple. 

But, at least according to Flavin, Stallone loved that they could also date like a regular couple. 

"I'd come over, and we'd watch a movie, cook dinner, goof around with the dog or walk on the beach," Flavin told People in 1994. She said other times Stallone would stop by her home in the Valley that she shared with her mother and sister.  

But it wasn't all rainbows and butterflies. Stallone had earned a reputation for allegedly cheating on his two former wives, and apparently, he and Flavin had a "no strings attached" agreement when they weren't together.

"I'm not naive about what may go on when I'm not around - he's a 45-year-old man - I can't change the way he is," she said to Cosmopolitan in 1992. "Still, he's not a cheating dog every day of the week. We spend five out of seven nights together, so I don't know where he'd find the time."

But he did find the time, even if it wasn't apparent to Flavin. After more than five years together, Stallone infamously sent his then-girlfriend a six-page, handwritten letter delivered right to her door to end their relationship. 

"You can't just write somebody off in a letter after six years," she said to People at the time. "It's not like I was going to try to beg him to come back to me or anything. I just wanted to talk."

Not included in the letter was the fact that Stallone had been cheating on her with a model and photographer named Janice Dickinson. In March 1994, when Flavin and Stallone ended things, Dickinson was pregnant with a baby everyone assumed was Stallone's. (A paternity test later revealed he wasn't the father.)

After Stallone pursued two more models - even getting engaged to swimsuit model Angie Everhart - he eventually found his way back to Flavin in the summer of 1995.  

"When they got back together it seemed they knew what they wanted," Flavin's older brother, Mitch, told People. "She knows that Sly is pretty much settled down. He's getting older too."

The two became inseparable, and she gave birth to their first daughter, Sophia Rose, in 1996. 

Third Time's the Charm

CANNES, FRANCE - MAY 24: Sylvester Stallone and Jennifer Flavin attend the screening of "Rambo - First Blood" during the 72nd annual Cannes Film Festival on May 24, 2019 in Cannes, France.

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While Stallone may have had his share of bad luck in relationships (some of it caused by himself, to be fair), the third marriage seems to have stuck. 

Stallone and Flavin tied the knot in 1997 during a civil ceremony at the Dorchester Hotel in London, followed by a chapel ceremony at Blenheim Palace in Oxfordshire. She wore a white Armani wedding dress and he wore a blue suit. They were surrounded by only a dozen close friends and family, including their nine-month-old daughter. 

The couple jetted off to Ireland for their honeymoon in the days after and started what would become Stallone's longest-lasting marriage. 

In a statement after the wedding, Stallone said: "I have had two great things happen to me in the past year: the birth of our beautiful daughter Sophia Rose and now my marriage to Jennifer, who is a great mother and I know will be a wonderful wife."

The pair clearly enjoyed their newlywed bliss because just over a year after they traded nuptials, they welcomed Sistine Rose into the world in 1998. Their third daughter, Scarlet Rose, followed in 2002.

And even if Stallone is seen as one of the most masculine men in Hollywood, he loves living in an all-girls household. 

"Everything in the house is female. The toys, the housekeeper, all the dogs. The one dog I have that's male is neutered. I'm next," he joked to The Telegraph in 2010. "But I've never had more fun."

In 2017, all three of the Stallone daughters were named Miss Golden Globes. The man of the household praised his wife in an interview with Entertainment Tonight for raising his girls.

"I'm just along for the ride. I'm stunned that life has moved by so quickly, and my daughters turned out so wonderfully," Stallone said. "I have to give Jennifer all the credit."

In January 2022, Flavin and Stallone appeared on their daughters' podcast, Unwaxed with Sophia and Sistine Stallone, and reflected on their roles in each other's lives. 

"I go through your schedule, and then you tell a few jokes, I laugh. That's what keeps us going, 'cause I laugh, and I laugh and I laugh, because he's so damn funny," Flavin said. "Sly is the funniest man I've ever met."

"I think she's fantastic. She's an amazing woman," Stallone said about his wife. "I tell her that every day. I don't know how she holds it together. She's just amazing."

And just a few months later, in May 2022, the pair celebrated 25 years of marriage. Stallone honored their years together on Instagram by writing, "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!"

A Bump in the Road

NEW YORK, NEW YORK - MAY 11: (L-R) Sylvester Stallone and Jennifer Flavin Stallone attend The Family Stallone Red Carpet & Reception at Torrisi Bar and Restaurant on May 11, 2023 in New York City.

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However, it wasn't long after they crossed that milestone that the public soon suspected there might be trouble in paradise. 

A tattoo artist posted that Stallone had a tattoo of his wife's face on his right bicep covered up with a photo of his Rocky character's dog, Butkus. The actor's representatives denied it was because his marriage was in a bumpy spot.

They told the Daily Mail: "Mr. Stallone intended to refresh the tattoo image of his wife Jennifer however the results were unsatisfactory and, unfortunately, unfixable. As a result, he had to cover the original image with a tattoo of his dog from Rocky, Butkus. Mr. Stallone loves his family."

But the public's suspicions were confirmed only a few weeks later when Flavin filed for divorce in August 2022, accusing Stallone of moving and wasting marital assets. Though the Cobra star disputed those claims in a court filing.

The day after the news of the divorce filing broke, an insider told People that the couple had been "unhappy for quite some time." And that the couple had "lots of issues for years and she just had enough."

But only a month later, the couple seemed to have reconciled. They filed an order of abatement to effectively put the divorce proceedings on hold. 

"They decided to meet back up at home, where they talked and were able to work out their differences," Stallone's rep told Page Six. "They are both extremely happy.

A source told People that Flavin had filed for divorce as a last-ditch option because she felt unheard and frustrated. But she had been much happier after they made up.

"She has been spending time with Sly and they are slowly figuring things out. Communication has been an issue in the past, but they are both working on communicating better," the insider said. "They are amazing together when they are happy. It really seems they will be able to work things out though."

At the Tulsa King premiere in November 2022, Stallone told Entertainment Tonight that he's learned to stop putting his career first.

"I used to have my priorities all screwed up, you know, work came first, and eventually, I came out of that delusional thinking, and they come first," he said. "So, to actually have them here, that's what it's all about."

And maybe their brief time apart was all they needed to rekindle their love. Stallone told USA Today shortly after reconciling, "My wife is magnificent. A very wonderful woman. She's super attentive, a great mother, a great companion so I'm a very lucky man.

And now, following the premiere of their family's reality show The Family Stallone last May, the two seem attached at the hip. For the seasoned actor, he's looking forward to the next season of his life with Flavin by his side. 

"Jen and my careers have been so crazy for so long," he told People. "I'm looking forward to a new chapter of life, slowing down for a change to spend some time with my girls. I won't be around forever, and I certainly want to leave them with fine thoughts of their father — that he did the best he could to make their life as fruitful as possible."

READ MORE: 'Tulsa King' Season 2: Everything We Know About the Return of Sylvester Stallone's Oklahoma-Bound Mafioso