Sylvester Stallone Opened Up About The Secret To His 23-Year Marriage to Jennifer Flavin

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Sylvester Stallone and his wife Jennifer Flavin have been together for 23 years, which is no small feat. They’ve weathered a lot together, including unimaginable grief. Despite such difficulties, though, the marriage has endured. And in 2010 the famous actor talked to the media about what he thought the secret to the relationship was.

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Flavin isn’t actually Stallone’s first wife, however, or even his second. The first woman Stallone married was a photographer named Sasha Czack. They wed in 1974 and had two sons: Sage and Seargeoh. But after Seargeoh was diagnosed as autistic, the relationship began to unravel. Czack gave up her career to care for their children – but Stallone did not.

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Stallone and Czack lasted more than a decade together, but then in 1985 they parted. Stallone told People magazine that year, “All of her priorities are geared toward finding a cure [for autism]. There is no fun in the future that way.” Czack did, though, receive in excess of $10 million for the split, which was reportedly the biggest settlement of its kind in U.S. history.

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After that, Stallone began dating actress Brigitte Nielsen, a woman almost 20 years his junior. They married quickly – indeed, the couple were husband and wife by the end of 1985. But it didn’t last, and it ended badly. They were together just 19 months before they divorced, in fact. Later, in 2014 Nielsen told Oprah: Where Are They Now? what happened.

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“If I would go back in time, I shouldn’t have married him,” Nielsen said on the show. “And he shouldn’t have married me! I don’t want to sit here and come across as an angel. I probably was also a pain in the butt at times… But it really just wasn’t for me, and it became very ugly, like some divorces do.”

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Stallone encountered Flavin in the late 1980s, still sore from his unsuccessful marriages and apparently not ready to jump into another commitment. There was a massive age difference between the two of them as well: Stallone was 42 and Flavin was in her late teens. Nonetheless, the couple subsequently began dating, although it was very far from smooth sailing at first.

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Flavin even seemed to accept that Stallone might cheat on her, in fact. In 1992 she informed Cosmopolitan magazine, “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. 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.”

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Not long after that, however, there came a massive blow for Flavin. In April 1994 Stallone sent her a breakup letter… via FedEx. This drew no small amount of comment in the media, and Flavin herself spoke to People magazine about the incident. She explained, “He sent me a six-page handwritten letter, in pen. It was pretty sloppy.”

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The pair had been dating for more than half a decade at that point. And there was more to the split than just the heartbreaking six-page letter. Flavin soon learned that Stallone had been cheating on her with photographer and model Janice Dickinson. Worse still, he was apparently the father of Dickinson’s newborn daughter.

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Of course, Flavin was devastated. She told People, “It hit me like a ton of bricks. I had no idea this was going to happen. We talked about us having children, about when I was going to get pregnant. We were already picking names, marking down names that he liked and I liked.”

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Furthermore, Flavin had met Dickinson before. The two women and Stallone had hung out at a Planet Hollywood restaurant, for example. Flavin recalled, “I’d always hear things, but he’d always kind of defuse the situation. He’d say, ‘Oh, she just wanted a picture with me’ or something like that… We had a good time together, but I never knew….”

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Flavin made no secret of how upset she was. “I cried a lot. I called all my friends. And I cleaned my apartment about five times. I had so many pictures and things to get rid of,” the model confessed. “You can’t just write somebody off in a letter after six years. It’s not like I was going to try to beg him to come back to me or anything. I just wanted to talk.”

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And there were still more twists to come in the story. For instance, Dickinson, too, had been cheating on someone when she became involved with Stallone: a Hollywood executive called Michael Birnbaum. She was absolutely convinced that the baby was Stallone’s – but in fact it wasn’t. A DNA test proved that the kid was Birnbaum’s.

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Despite this revelation, though, Stallone didn’t get back together with Flavin. Instead, he fell into another relationship, this one with 25-year-old supermodel Angie Everhart. By the spring of 1995 the pair had released a joint statement saying they were going to be married. It read, “We are very much in love, and we couldn’t be happier.”

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It didn’t work out in the end, however. Everhart and Stallone broke up, and Stallone went back to Flavin. Finally, a happy ending appeared to be on the horizon. Then, in 1996 Flavin had her first child with Stallone. This was a little girl called Sophia Rose – but unfortunately she was born with a serious medical problem.

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Sophia Rose had a hole in her heart, in fact, and so needed to undergo an operation. Thankfully, it was a success. A statement from Stallone explained, “I’ve been staying at the hospital with Jennifer every night. I have been blessed with two miracles within the past nine weeks – that of my daughter being born and that of my daughter being reborn.”

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The following year, 1997, Stallone and Flavin finally walked down the aisle. They wed in London, at the famous Dorchester Hotel, before going on to Blenheim Palace for the reception and blessing. Stallone sported a blue suit and Flavin a white gown from Armani. And by all accounts, the couple were absolutely over the moon.

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Stallone released a sweet statement to the press at the time. It read, “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.” Little Sophia Rose was also present at the wedding.

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The couple went on to have two more children. Sistine came along in 1998 and then Scarlet was born four years later. Just like their father, and their half-brothers Sage and Seargeoh, they all had names beginning with “S.” Things were looking promising for the whole family unit – but then in 2012 tragedy struck.

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In July of that year, Stallone’s oldest child Sage was found dead at his house in LA. He’d been only 36 years old, was engaged and had a career in movies that was going well. Needless to say, his passing was devastating for the family. What’s more, Stallone not only had to grieve his son, but he also had to dispel rumors that drugs had killed Sage.

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Stallone made a statement to CNN that read, “When a parent loses a child there is no greater pain. Therefore I am imploring people to respect my wonderfully talented son’s memory and feel compassion for his loving mother Sasha, because this agonizing loss will be felt for the rest of our lives. Sage was our first child and the center of our universe and I am humbly begging for all to have my son’s memory and soul left in peace.”

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In the end, it transpired that it wasn’t drugs that had killed Sage, but a heart attack. His friend and attorney George Braunstein told People magazine, “Sage was a really young, very sensitive and very talented kid. There has been no indication that there was anything wrong in his life… He was close to both of his parents and looked up to them.”

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Unfortunately, though, the death of Sage wasn’t the only tragedy Stallone and his family would face that year. Less than two months afterwards, Stallone’s half-sister Toni Ann Filiti passed away due to cancer at the age of 48, leaving a child behind. All Stallone could do was try to support his nephew in the wake of it all.

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And even that wasn’t all life would throw at Stallone during 2012. Though her heart had been saved by doctors when she was still a baby, Sophia began suffering cardiac problems again that year. Just a week before Christmas, she had to have her heart operated on once more.

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Flavin was, of course, also devastated about all the terrible events that had happened in such quick succession and was deeply saddened for her husband. “This is a terrible year, a horrible year for him,” she told Hello magazine. “Sylvester is devastated, but he refuses to talk about his son.”

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Thankfully, Sophia’s heart surgery went well. After that, the family were able to settle down and focus on each other and their careers. All three of the Stallone daughters went on to model as they grew older. And the marriage between Stallone and Flavin seemed to only strengthen with the passing of time.

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So, what was the secret to their successful Hollywood marriage? Stallone himself provided an answer in 2010 when speaking to The Daily Telegraph newspaper. “Everything in the house is female,” he explained. “The toys, the housekeeper, all the dogs. The one dog I have that’s male is neutered. I’m next… But I’ve never had more fun.”

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Regarding the secret to his marriage, Stallone added, “It took me 19 years to realize she’s always right. I realized that women have a knack, at least Jennifer, for making incredibly erudite, wise, smart decisions. I always leap without looking. She always looks and never leaps. She’s incredibly safe. So now finally, I say, ‘Honey, you make all the decisions. Done, done, done. I trust you.’”

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The A-lister had said a similar thing a few years prior in an interview with Parade magazine. When asked what keeps him on track through tough times, Stallone answered, “I learned the hard way, it took me 30 years to figure out: happy wife, happy life. So it’s give up and give in when you have a little disagreement.”

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“When you are going to argue, make sure it’s a big deal,” Stallone continued. “Don’t take a stand on which TV show you want to watch. Just go to another room. I have brilliantly learned for the first time how to have a great, fantastic wife. I can now write, I can now think, and I feel that I have something important to prove.”

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Flavin herself was asked about the secret of her successful marriage in 2007. And she, too, gave a good answer. It was because both of them are financially independent, she said. She told Haute Living magazine that since her and Stallone both made plenty of money, Flavin didn’t strictly “need” him.

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“I think that is why we have lasted so long,” the actress-turned-businesswoman explained. “Because of my success, because I feel better about myself, I am not trying to go out and get an acting job at 40 and feeling like, ‘Oh, God, my career is over!’ My career is just beginning. And what keeps it going is that I don’t need Sly. I don’t need him financially, and I don’t need him to get me a job.”

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Clearly, the relationship was, after a rocky start, a good one. And by all accounts Stallone and Flavin have been good parents to their three daughters, too. In 2015 the 16-year-old Sistine began striking out on her own as a model, and she spoke to Teen Vogue magazine about what her childhood had been like.

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“I have followers because of my dad. I get asked about his movies once a week,” Sistine said. “They want to know how he stays in shape and if he writes the screenplays.” She added that Rocky was her favorite Stallone movie and that her father had taught her “how to throw a punch.”

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Sistine admitted that she probably wouldn’t go into acting, as she was “horrible” at it, but wanted to be a model like her mother. Of Flavin, the teenager added, “She’s like my wingman. She’s taught me my good side, my bad side, how to walk for the runway, and how to become someone else in a certain outfit.”

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All three Stallone daughters then did an interview with Harper’s Bazaar in 2017. That was the same year they’d served as on-stage attendants at the Golden Globe Awards, all of them sharing the title of “Miss Golden Globe.” They gushed about the experience to the magazine, sharing how exciting it had been to meet so many celebrities.

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The Stallone girls’ mother was also there for the interview. At the time, Sophia Rose was 20, Sistine 18 and Scarlet just 14. Offering an inside look into her parenting, Flavin told the interviewer, “They’re all totally different. But I expect them all to work hard and do well with whatever they’re good at.”

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Despite initially not wanting to act, Sistine did subsequently sign up for a movie, 47 Meters Down: Uncaged, in 2019. She did an interview with Schön! magazine to promote the film, and again spoke about the influence of her mom and dad. Sistine said, “My parents have always taught me to keep my blinders on and focus on my future, [and that] no one else should be able to dictate my path.”

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Their daughters are growing older and branching out, but Stallone and Flavin seem every bit as in love as ever. She often posts pictures of herself and Stallone on Instagram, showing them having date nights and the like. And she captions them with cute messages such as: “My love forever.”

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While it’s safe to say that Flavin hasn’t forgotten the past and all the difficulties she and her husband have faced, she nonetheless seems to look back on them with a healthy attitude. For Valentine’s Day 2019, she posted a photograph and the message, “Our first photo taken together 30 years ago! July 1988! LOVE LASTS!”

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