Sylvester Stallone and Jennifer Flavin Celebrate 27th Wedding Anniversary: A Timeline of Their Marriage

On May 17, 2024, the couple rang in 27 years of marriage.

Sylvester Stallone and Jennifer Flavin, officially have 27 years of marriage under their belts. 

In honor of the longtime Hollywood couple's wedding anniversary, ET is looking back at their romance spanning 36 years, nearly three decades of marriage, and three children. 

Things haven't always been easy for the couple, so much so that Flavin filed for divorce in 2022. That didn't last long, though, and now the family seems to be better than ever, even starring side by side in their own Paramount+ family reality series, The Family Stallone

Keep reading for a recap of the highs and lows of their Hollywood romance.

From the Beginning...

Stallone and Flavin first met in 1988 at a restaurant in West Hollywood, California, when Stallone was at the height of his career. Flavin, 19 at the time, was dining out with a friend. At that point, Stallone was a bona fide A-list actor with several blockbuster films under his belt, including several Rocky and Rambo films. They dated for six years before splitting, and it was how Stallone ended things that really grabbed everyone's attention. 

Stallone and Flavin's relationship ended on March 11, 1994, after Stallone FedEx'd her a handwritten -- albeit, sloppy -- letter to inform her of the split. According to Yahoo, Flavin received a FedEx package with a "Dear Jennifer" letter in it. It was six pages, though no word if it was front and back.

Flavin would later reveal to People, "I cried a lot... 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."

Shortly after, the Rocky star started dating model Janice Dickinson. They would ultimately become engaged but, according to reports, the couple split after a paternity test proved Stallone was not the father of Dickinson's daughter, Savannah.

Flavin told People that she later learned from her agent at the Elite Modeling Agency the real reason why Stallone abruptly ended things with her, a handwritten note notwithstanding. According to the outlet, Flavin learned that Stallone was having an affair with Dickinson.

"It hit me like a ton of bricks," she said at the time. "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."

They Tie the Knot in London

In 1995, Stallone and Flavin reunited and they welcomed their first daughter, Sophia, on Aug. 27, 1996. Stallone and Flavin would ultimately get married in the Penthouse Pavilion at the Dorchester Hotel in London on May 17, 1997.

The intimate civil ceremony drew a lot of attention from the media, for obvious reasons. According to People, Stallone donned a blue suit while Flavin wore a white Armani wedding dress. Sophia, nine months old at the time, was also in attendance. The magazine reported that limos whisked them to the wedding party some 60 miles to the birthplace of Winston Churchill, Blenheim Palace. They later hopped on a jet and celebrated their honeymoon in Ireland.

"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 at the time.

But, at this point, Flavin would be his third wife. He first married Sasha Czack in 1974 when he was 28. They had two sons -- Sage, who died in 2012 at 36 from a heart attack, and Seargeoh. Stallone and Czack divorced in 1985.

He married model and Rocky IV co-star Brigitte Nielsen in 1985 but divorced two years later. 

Stallone and Flavin Complete the Trifecta

The couple would later welcome daughters Sistine on June 27, 1998 and Scarlet on May 25, 2002.

In a 2010 interview with The Telegraph, Stallone opened up about living in a female-dominated household -- a stark contrast to the testosterone-fueled sets he produced and starred in -- and how much Flavin had changed his outlook on life and the dominant role she plays in their 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. "But I've never had more fun. I learned that from my wife. 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.' I never had that before. Ever."

Flavin Turns 50 

On Aug. 14, 2018, Stallone took to Instagram and posted a side-by-side photo of them from back in the day to the present. In the throwback photo, Stallone looks stoic. In the second photo, he's smiling into the camera and Flavin flashes her smile, too.

He captioned the post, "Congratulations to my wife on her 50th birthday!!! We’ve been together a long time and I’m very lucky to have met such a fantastic woman."

Daughters Are All Grown Up 

Gregg DeGuire/WireImage

In 2017, Stallone and Flavin beamed with pride after their daughters -- Sophia, Sistine and Scarlett -- are all named Miss Golden Globes 2017. In an exclusive interview with ET at the time, Stallone was in awe of the honor while giving Flavin all the credit for raising three wonderful children.

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

Two years later, Stallone appeared at a red carpet premiere, but it wasn't for one of his films. He was there to support Sistine's movie47 Meters Down: Uncaged

"Honestly, I feel a bit speechless. I don't really know how to feel. This is the first time it's my thing so that's really cool and hopefully this isn't my first and only carpet," Sistine told ET at the time. 

And while Stallone gave his daughter some space when it came to filming the movie, he made sure to offer her some advice. 

"[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 revealed. 

The couple celebrated another big occasion on May 10, 2019, when Sophia became their first daughter to graduate from college. Sophia donned her cap and gown from USC in a photo Stallone shared on Instagram. He captioned it, "Our daughter SOPHIA graduates from USC !!!! An absolutely amazing day for us all. So proud!!!"

Thinking of Life Without Each Other

On an episode of their daughters' podcast, Unwaxed With Sophia and Sistine Stallone, that was released on Jan. 31, the actor and his wife opened up about their marriage. When Sistine noted that her parents are "polar opposites" but "literally cannot live without one another," Flavin responded, "That's true." 

Sistine called out her mom's "organizational skills" for helping the movie star all these years. "If she was out of my life, it would be mass suicide -- which infers that I have multiple personalities," he responded. 

"I keep him extremely organized, so I do everything. I do everything from the minute we wake up, from getting him coffee to bringing it to him in bed, bringing him cookies in bed every morning, then going downstairs. And then we get ready. I make you breakfast in the morning, and then I make sure everything is great for you for the day," Flavin said of their daily routine. "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. Sly is the funniest man I've ever met, and I'm telling you I've sat with a lot of funny comedians. He cracks me up."

When asked what he does for his wife, Stallone responded, "I just aggravate the hell out of her. I don't really know what I do for her. I mean, she knows I would jump in front of a small train, just like this big, a choo-choo train, I would put my arm in front of it. No, I think she's fantastic. She's an amazing woman. I tell her that every day. I don't know how she holds it together. She's just amazing."

25th Wedding Anniversary 

Stallone and Flavin celebrated a milestone anniversary earlier this year when they hit the 25-year wedding mark. 

"Happy 25th anniversary to my amazing wife," Stallone gushed alongside a series of images of him and Flavin. "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!"

Flavin shared her love for Stallone in the comments section, writing, "Thank you my love! I love you so much and we will be spending the next 25+ years together! Keep me laughing and I’m yours for the rest of my life!"

Flavin also took to Instagram to commemorate the occasion with her own post.

"Happy 25th wedding anniversary to us! 🥰❤️❤️❤️ Thank you for always keeping me laughing, loving and protecting our beautiful family!" Flavin wrote. "Our marriage keeps getting better every year! I can’t wait to spend the rest of our lives together."

The Cover-up

An Aug. 22 report in the Daily Mail revealed that there was trouble in paradise, after Stallone covered up the portrait of his wife located on his bicep. The new ink was revealed in since-deleted pictures that were posted by artist Zach Perez. 

Flavin's face was replaced by a photo of Stallone's character, Rocky’s, bull mastiff Butkus. The new ink led fans to question if there were issues between the couple.

The actor's rep tried, to no avail, to downplay the tattoo cover-up, telling the Daily Mail that nothing was amiss and there was no cause for alarm, saying, "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," the statement continued. "Mr. Stallone loves his family. The Stallones are presently filming a reality show together which will debut on Paramount+."

But the cover-up was far from the only sign the marriage may have gotten, er, rocky. Eagle-eyed fans also noticed that Flavin apparently unfollowed Stallone on Instagram.

In a recent post by Flavin, she seemingly shaded Stallone after sharing a picture of her and their three girls, with the caption, "These girls are my priority ❤️ nothing else matters. The 4 of us forever. #truth #family #forever."

Flavin Files for Divorce 

ET confirmed on Aug. 24 that Flavin filed for divorce in Florida. According to the filing, she wants to remain living in the couple's home in Palm Beach, Florida, amid the divorce proceedings. She also believes her husband is hiding marital assets. 

"Upon information and belief, the Husband has engaged in the intentional dissipation, depletion and/or waste of marital assets which has had an adverse economic impact on the marital estate. Pursuant to Section 61.075, Florida Statues, equity dictates that the Wife be compensated and made whole by receiving an unequal distribution of the marital assets in her favor. Moreover, the Husband should be enjoined from, selling, transferring, assigning, encumbering, or dissipating any assets during the pendency of proceedings," read the divorce docs.

Additionally, Flavin wants to keep her last name.

Fight Over Dog Triggered Divorce?

According to TMZ, citing sources directly connected to the couple, Flavin filed for divorce shortly after getting into an argument with Stallone over whether he could get another dog. The outlet reported on Aug. 24 that Stallone wanted a Rottweiler but she didn't want another dog. The argument apparently got heated, and other issues were brought up, but none that would destroy a longtime marriage. 

Neither budged on their position over the dog, except Stallone broke the stalemate when he reportedly went ahead and got the dog, named Dwight, which is the name of his character in his TV show, Tulsa King.

TMZ reported that Stallone was in Oklahoma filming the show when he found out Flavin filed for divorce.

Stallone Pushes Back

On Aug. 29, Stallone filed a response to Flavin's divorce docs, obtained by ET, in which he denied several of his estranged wife's claims and requests.

Stallone denied her allegations that he has engaged in the "waste of marital assets" and argued that he "has not engaged in any conduct which constitutes intentional dissipation, depletion and/or waste of marital assets." Stallone also denied Flavin's request to have exclusive use and occupancy of their home in Palm Beach, Florida. He also denied Flavin's request for the option to join in any of his business entities or corporations in the future. 

Stallone accepted several of Flavin's other requests, including her desire to restore her maiden name and an equitable distribution of their joint assets and liabilities. 

Divorce Is Called Off

Stallone raised eyebrows the next month when he posted a photo of him and Flavin holding hands. While it was unclear at the time if it was a throwback pic or not, things continued on a friendly path for the duo when they agreed to a peaceful termination of their union. 

A total about-face followed as the pair called off their divorce and decided to reconcile. The next month, the couple was spotted displaying PDA and even stepped out for an event together.

The Reality Show

Amid the reconciliation, talk swirled about The Family Stallone, the reality show in which Stallone, Flavin and their daughters will star. While speaking to The Hollywood Reporter in November, Stallone confirmed that his marital woes would be featured on the series.

"Of course it’s part of the show," he said. "It’s the John Lennon thing: 'Life is what happens when you’re making other plans.' Hopefully, you’re involved with people who understand the foibles of life and the fragility of it and how rare a real good relationship is. Sometimes I put the work ahead of [my family], and that is a tragic mistake which won’t happen again."

Stallone added, "What you will see is the real truth. This is a great opportunity. I don’t look at it as stooping to conquer. But each time you go in a different direction, people go, 'Oh God, you must be in trouble.' Just the opposite."

That same month, Stallone told ET, "I used to have my priorities all screwed up, work came first, and eventually, I came out of that delusional thinking, and they come first."

In a follow-up interview with ET, Stallone expanded on his decision to prioritize his family over his career.

"In the past few years when you find yourself obsessing about, 'Oh what's the next move? How do I compete with this situation or this character or this guy's getting this role,' and I said, 'Jesus Christ, what does it matter?'" Stallone said. "Because the things that really matter, the things that are actually your flesh and blood, are moving on... The priority is the things that you're responsible for. You brought them on this planet. You must guard them with your life."

ET spoke to the actor again in May, and he opened up about his turn to reality TV, explaining, "I love daughters, I love my wife and I wanted to share that."

Flavin agreed, noting, "I didn't want it to be set up. I didn't want it to be, 'Oh, we all get drunk and we all throw fits and we're screaming at each other.' I wanted to show people real-life things that happen."

27 Years Down

On May 17, 2024, the longtime couple celebrated their 27th wedding anniversary. The celebrity pair marked the occasion with tributes to each other on Instagram.

"27 years with the love of my life," the blockbuster action star wrote to his other half along with photos from their 1997 wedding.

Flavin returned the favor while reminding fans that they've been together for nearly a decade more than they've been married. "Happy Wedding Anniversary my love! 27 years!!!❤️🎉🎉🎉36 years of us being together!!💘💘💘," she wrote in her own Instagram post. "I’m blessed in life to have true love and having wonderful kids! Couldn’t ask for more❤️❤️❤️." Days earlier, Stallone marked Mother's Day with a touching tribute to his beloved wife. Using a clip from their reality TV show, he told Flavin, "I have eternal love for you."