Twenty-seven years of marriage were celebrated by the pair on May 17, 2024.
According to official records, Sylvester Stallone and Jennifer Flavin have been married for a total of 27 years.
In celebration of the legendary Hollywood couple’s wedding anniversary, Entertainment Tonight is taking a look back at their romance that has lasted for 36 years, in addition to their almost three decades of marriage and three children.
There have been times when things have been difficult for the pair, to the point that Flavin filed for divorce in the year 2022. That didn’t last long, however, and today the family seems to be doing better than they ever had before. They even star in their very own family reality series on Paramount+ called The Family Stallone, which they appeared in together.
Read on for a summary of the highs and lows that occurred throughout their romantic relationship in Hollywood.
The first time that Stallone and Flavin met was in 1988, when Stallone was at the pinnacle of his fame and Flavin was working at a restaurant in West Hollywood, California. At that time, Flavin, who was 19 years old, was having dinner with a buddy. It was at that time that Stallone had established himself as a genuine A-list actor, having already starred in a number of critically acclaimed films, including a number of Rocky and Rambo flicks. They had a relationship that lasted for six years until they broke up, and the manner in which Stallone terminated things was the thing that really caught everyone’s attention.
The relationship between Stallone and Flavin came to an end on March 11, 1994, subsequent to Stallone sending Flavin a handwritten note by FedEx, although one that was sloppy, in order to tell her of the breakup. There was a note addressed “Dear Jennifer” that was included in the FedEx box that Flavin received, as reported by Yahoo. It was six pages long, but there was no indication as to whether it was front and back.
It was later that Flavin would disclose to People, “I shed a lot of tears… After a period of six years, it is not possible to just dismiss someone in a letter. It’s not like I was going to attempt to grovel or anything like that in order to get him to come back to me. I want to have a conversation.
Very quickly after that, the Rocky actor had a relationship with the model Janice Dickinson. However, according to sources, the pair ended up breaking up when a paternity test revealed that Stallone was not the father of Savannah, Dickinson’s daughter. Despite the fact that they had eventually been engaged, the couple separated.
In an interview with People, Flavin said that she had subsequently uncovered the exact reason why Stallone suddenly stopped things with her from her agency at the Elite Modeling Agency. This was despite the fact that Stallone used a handwritten message. Flavin reportedly found out that Stallone was having an affair with Dickinson, as stated by the publication.
She claimed at the time, “It hit me like a ton of bricks,” referring to the impact of the event. “I had no notion that any of this was going to take place. During our conversation, we discussed the possibility of us having children and the timing of my pregnancy. The process of selecting names had already begun, and we were noting down choices that he and I both liked.
The year 1995 saw the reunion of Stallone and Flavin, and on August 27, 1996, they became parents for the first time to a daughter named Sophia. The wedding that would finally take place between Stallone and Flavin took place on May 17, 1997, in the Penthouse Pavilion of the Dorchester Hotel at London.
For reasons that are rather self-explanatory, the media paid a great deal of attention to the private civil ceremony. According to People, Stallone wore a blue suit, while Flavin wore a white Armani wedding dress. Both figures were photographed during the event. Additionally there was Sophia, who was nine months old at the time of the event. It was said in the magazine that limousines transported them to the wedding celebration, which was located around sixty miles away at Blenheim Palace, the spot where Winston Churchill was born. Following that, they boarded a private plane and traveled to Ireland to enjoy their honeymoon.
“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,” Stallone said in a statement that was released at the time.
On the other hand, Flavin would be his third wife at this point in time. He wed Sasha Czack for the first time in 1974, when he was 28 years old. Sage, who unfortunately passed away in 2012 at the age of 36 due to a heart attack, and Seargeoh were their two boys. In 1985, Stallone and Czack finalized their divorce.
He tied the knot with Brigitte Nielsen, a model and Rocky IV co-star, in 1985, but they separated two years later at the time.
Flavin and Stallone are the last members of the trifecta.
In following years, the couple would become parents to two daughters: Sistine, born on June 27, 1998, and Scarlet, born on May 25, 2002.
As part of an interview with The Telegraph in 2010, Sylvester Stallone discussed his experiences of living in a family that was ruled by women. This was a dramatic contrast to the testosterone-fueled sets that he produced and played in. He also discussed the extent to which Flavin had altered his perspective on life and the dominating position that she plays in their household.
The whole of the home is comprised of females. Including the maid, the toys, and all of the pets. I have neutered the one male dog that I have in my possession. The joke was directed at me. In contrast, I’ve never had a better time. My wife was the one who taught me that. I didn’t know that she was always correct until I was 19 years old. I came to the realization that women, and Jennifer in particular, have a flair for making judgments that are really erudite, insightful, and intelligent. Every time I jump, I do it without seeing. She never jumps, however, and she always looks. She poses a significant threat. Finally, I say to my wife, “Honey, you are the one who makes all of the decisions.” Finished, finished, and finished. I put my faith in. That was something I had never experienced before. At any time.”
Taking to Instagram on August 14, 2018, Stallone shared a snapshot of the two of them that was a side-by-side comparison of their appearance from the past to the present. According to the vintage shot, Stallone seems to be unmoved. In the second picture, he is smiling directly at the camera, and Flavin is also smiling at the camera simultaneously.
“Congratulations to my wife on her 50th birthday!!!” was the message under which he posted the photo. We have been together for a very long time, and I want to express how fortunate I am to have found such a wonderful lady.
During the year 2017, Stallone and Flavin were filled with pleasure as they announced that their three children, Sophia, Sistine, and Scarlett, had all been selected as Miss Golden Globes. During that time, Stallone gave an exclusive interview to ET in which he expressed his admiration for the distinction, but he also gave Flavin all the credit for the fact that he was able to raise three lovely children.
“I’m just along for the ride,” Stallone said to ET at the time after the event. It’s hard for me to believe that time has passed so rapidly, and that my children have developed into such great people. There is no one else I can give credit to except Jennifer.
Two years later, Stallone made an appearance at a premiere event that had a red carpet, but it was not for one of his films. In order to show his support for Sistine’s film, 47 Meters Down: Uncaged, he was there.
“To tell you the truth, I am a little bit unmoved. I’m not really sure how I should be feeling. During that time, Sistine expressed her excitement to ET by saying, “This is the first time it’s my thing, so that’s really cool, and hopefully this isn’t my first and only carpet.”
When it came to the making of the movie, Stallone made sure to provide his daughter with some guidance, even though he left her some freedom to make her own decisions.
“[My dad] wanted the director’s note to be, instead of swimming away, confront the shark head-on — which I don’t think would’ve played out well,” Sistine said to us.
On May 10, 2019, the couple celebrated yet another momentous anniversary, which was the graduation of their first daughter, Sophia, from college. In a snapshot that Stallone posted on Instagram, Sophia was seen wearing the United States of America cap and gown. “Our daughter SOPHIA graduates from USC!!!!” was the message that he added to the photo. A day that was just incredible for all of us. How proud I am!!!
In an episode of their daughters’ podcast, titled “Unwaxed With Sophia and Sistine Stallone,” which was published on January 31st, the actor and his wife discussed their marriage in detail. In response to Sistine’s observation that her parents are “polar opposites” yet “literally cannot live without one another,” Flavin said, “That’s true.”
Sistine praised her mother’s “organizational skills” for the tireless assistance she has provided to the movie star over the years. “If she was out of my life, it would be mass suicide — which infers that I have multiple personalities,” he said in response.
As a result of my ability to keep him incredibly structured, I am responsible for everything. From the moment we get up, I am responsible for everything, including fetching him coffee and giving it to him in bed, bringing him cookies in bed every morning, and then going downstairs. The next step is to get ready. “In the morning, I prepare breakfast for you, and then I make sure that everything is in order for you to have a wonderful day,” Flavin remarked in reference to their typical routine. While I am going through your agenda, you will tell me a few jokes, and I will chuckle at them. Because he is so damn amusing, that is what keeps us going, because I laugh, and I laugh, and I laugh, because he is such enjoyable to be around. I have sat with a lot of hilarious comedians, and I can honestly say that Sly is the funniest guy I have ever had the pleasure of meeting. He makes me laugh out loud.
Stallone had the following response when he was asked what he did for his wife: “I just aggravate the hell out of herself.” I am not really sure what it is that I do for her. I mean, she is aware that I would place my arm in front of a choo-choo train, which is a large train, just as she knows that I would leap in front of anything that was little. No, I think she is just wonderful. Wow, she is an incredible lady. Each and every day, I tell her that. I have no idea how she manages to keep it all together. “She is simply incredible.”
Anniversary of the 25th Wedding:
When they reached the 25-year wedding anniversary earlier this year, Stallone and Flavin celebrated a momentous occasion together with their anniversary.
Stallone gushed, “Happy 25th anniversary to my amazing wife,” while putting up a series of photographs of himself and Flavin at the celebration. “There are not enough words to describe what this woman has meant to our lives; she is so incredibly selfless, dedicated, and patient. I only wish that she could be another 25 years old!” Thank you very much, my darling!
In the comments area, Flavin expressed her affection for Stallone by saying, “Thank you my darling! I love you so much, and I know that we will be together for the next twenty-five years and beyond. Please continue to make me laugh, and I will be yours for the rest of my life!
Additionally, Flavin posted a post on Instagram to remember the event, which she did on her personal account.
We are celebrating our 25th wedding anniversary today! 🥰❤️❤️ᝤ️ I want to express my gratitude for all the times you have made me laugh, loved, and protected our wonderful family. As Flavin put it. “Every year, our marriage continues to improve and become stronger! When we finally get to spend the rest of our lives together, I can’t wait.
The Daily Mail published an article on August 22 that claimed that there was problems in paradise. The article said that Stallone had covered up the photo of his wife that was positioned on his bicep. The new tattoo was seen in photographs that have since been removed from the internet and were shared by the artist Zach Perez.
A picture of Rocky’s bull mastiff, Butkus, was used in lieu of Flavin’s face. Rocky is the character played by Sylvester Stallone. The new tattoo caused admirers to speculate about whether or not there were problems between the pair.
The actor’s representative made an unsuccessful attempt to minimize the tattoo cover-up. He told the Daily Mail that there was nothing wrong and that there was no need to be concerned. He said, “Mr. Stallone intended to refresh the tattoo image of his wife Jennifer; however, the results were unsatisfactory and, unfortunately, unfixable.”
Additionally, the statement proceeded by saying, “As a consequence of this, he was forced to cover the original image with a tattoo of his dog, Rocky, butkus.” “Mr. Stallone has a deep affection for his family. In the current day, the Stallones are working together to produce a reality program that will be shown on Paramount+.
However, the cover-up was not the only indication that the marriage may have been complicated, to put it mildly. Fans with keen eyes would also have observed that Flavin seems to have removed Stallone from his Instagram followers.
After posting a photo of herself and her three daughters with the remark, “These girls are my priority ❤️ nothing else matters,” Flavin seemed to be making a snide comment about Stallone in a recent post. The four of us for all time. The truth, the family, and the forever.”
Divorce petitions filed by Flavin
On the 24th of August, ET revealed that Flavin had filed for divorce in the state of Florida. During the course of the divorce procedures, she is requesting that she be allowed to continue residing in the house that she and her husband shared in Palm Beach, Florida. Additionally, she is under the impression that her spouse is concealing assets that belong to the marriage.
“Based on the evidence and belief that has been gathered, it has been determined that the Husband has been intentionally dissipating, depleting, and/or wasting marital assets, which has resulted in a negative economic effect on the marital estate. According to Section 61.075 of the Florida Statutes, equity requires that the Wife be paid and made whole by an uneven distribution of the marital assets in her favor. This is in accordance with the provisions of the statute. During the time that the divorce processes are ongoing, the documents for the divorce provide that the husband should be prohibited from selling, transferring, assigning, encumbering, or dissipating any assets.
Over the course of the previous several years, every time you find yourself preoccupied with the question, “Oh, what’s the next move? In response to the question, “How am I supposed to compete with this circumstance, this character, or this guy who is getting this role?” I said, “Jesus Christ, what does it matter?” “Stallone declared,” Due to the fact that the things that really matter, the things that are literally your flesh and blood, are going on… You should give the things that you are accountable for the highest priority. They are here on this earth because of you. You are obligated to use your life to protect them.
In May, ET had another conversation with the actor, during which he discussed his decision to participate in reality television. He said, “I love daughters, I love my wife, and I wanted to share that.”
With a nod of agreement, Flavin said, “I didn’t want it to be set up.” ‘Oh, we all get drunk and we all throw tantrums and we’re yelling at each other,’ was not the kind of thing I wanted to describe the situation. “I wanted to show people things that actually take place in real life.”
27 Years Have Passed
On May 17, 2024, the long-term couple celebrated their 27th wedding anniversary. They had been married for 27 years. Instagram posts that paid respect to each other were posted by the famous couple to commemorate the event.
Including photographs from their wedding in 1997, the blockbuster action actor wrote to his significant other, “27 years with the love of my life,” and sent the images.
It was Flavin who returned the favor by bringing to the attention of his admirers the fact that they had been together for over ten years longer than they have been married. “Wedding Anniversary, my love! Happy Anniversary!” It’s been 27 years!!!❤️🎆🎉🎉We have been together for the last 36 years!💘💘💘,” she stated in a photo that she made on her own Instagram account. “I am fortunate in life to have a genuine affection for my children and to have lovely children! We could not have asked for anything better. A few days previously, Stallone celebrated Mother’s Day by paying a heartfelt homage to his cherished wife for the occasion. On their reality television program, he told Flavin, “I have eternal love for you.” He used a footage from the show.