An Inside Look At Sylvester Stallone's Marriage

When it comes to romantic relationships, Sylvester Stallone's life has had more ups and downs than Rocky Balboa. The action hero first said "I do" to Sasha Czack and welcomed two sons back when he was a relative unknown in the mid-1970s, but just over a decade later the pair headed for the divorce courts. Stallone's second wife was fellow actor Brigitte Nielsen but their marriage fizzled out even quicker: within two years Stallone was once again a single man.

The Hollywood icon's rollercoaster romantic life continued in the 1990s when he and model Janice Dickinson called off their engagement, while another model, Angie Everhart, briefly came onto the scene before Stallone's one true love (and another former squeeze) made a honest man out of him for a third time in 1997.

Of course, Stallone and Jennifer Flavin's marriage has been anything but smooth. From FedEx kiss-offs to temporary divorce proceedings, here's a look at the couple's turbulent love story.

In the same year she signed up to the Elite Modeling Agency, 19-year-old Jennifer Flavin first met one of Hollywood's biggest action superstars. And although Sylvester Stallone was more than twice her age, a two-time divorcee and a father of two, it proved to be love at first sight.

Perhaps mindful of the age gap, the pair took their time before going public. Per People, it was only in 1990 that Stallone and Flavin made their red carpet debut together at a gala in Los Angeles. And they looked the height of glamor as they linked arms while dressed in matching style. However, even by Hollywood standards, their romance was slightly unconventional, with Stallone reportedly saying in 1991 (via Page Six), "When we come together, it is wonderful. When we are separate, there are no strings attached. That's the way it is. No strings."

Flavin also appeared to be on board with this arrangement. In 1992, she was quoted as saying (via Page Six), "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."

You thought that rumor about Phil Collins asking for a divorce over fax was bad? (For the record, the musician denied doing so.) Well, it has some stiff competition from Sylvester Stallone. As Yahoo! Entertainment recounted, the "Rambo" star dumped Jennifer Flavin back in 1994 with a sloppily-handwritten six-page letter sent by Federal Express.

Although it was a somewhat lengthy kiss-off, Stallone still managed to avoid telling Flavin the exact reason behind it. It was only several days later that the model discovered he'd actually been seeing Janice Dickinson on the down low. To add insult to injury, the future "America's Next Top Model" judge then gave birth to a daughter, Savannah Rodin, who was said to be Stallone's. Flavin told People, "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."

Stallone's relationship with Dickinson fell apart when he discovered that he wasn't Savannah's father. The Golden Globe winner then went crawling back to Flavin, who despite previously getting rid of everything in her apartment reminiscent of him, appeared to forgive and forget.

Action movie icon Sylvester Stallone has stayed ripped, even well into his 70s. But you will never see him showing it off while in bed with another actor. Well, not since filming his last ever sex scene in 1994's "The Specialist," anyway.

Stallone had to get hot and heavy with Sharon Stone for the action thriller, but Jennifer Flavin wasn't particularly comfortable with her then-boyfriend getting so intimate with one of Hollywood's biggest sex symbols. According to the Irish Examiner, he once said, "Jennifer does not believe you can just be acting and thinks there must be some kind of romantic attachment. I hated doing it and Jennifer was upset so I knew that would be the last time for me."

On the flip side, Stone wasn't particularly enamored with the idea of getting naked on camera again herself. Stallone told Ain't It Cool News that the "Basic Instinct" star took some coaxing to disrobe for their shared shower scene and revealed the slightly questionable method he used to put her at ease: "I went down to my trailer, brought back a bottle of Black Death vodka that was given to me by Michael Douglas and after half-a-dozen shots we were wet and wild."

Just two years after the paternity drama involving Janice Dickinson, Sylvester Stallone and Jennifer Flavin welcomed daughter Sophia Stallone. The couple was certainly put through the emotional wringer at the time.

As per the Los Angeles Times, Sophia was forced to undergo surgery just days after being born when doctors discovered that she had a hole in her heart. Luckily, the operation carried out at UCLA Medical Center was a huge success and mom and dad were able to take their newborn home. The Los Angeles Times reported that two years later Sylvester donated a significant amount of money to the nonprofit Heart of a Child Foundation to express his gratitude.

Sophia has since graduated from USC with a degree in fashion, and also co-hosts podcast "Unwaxed" with sister Sistine Stallone. The celebrity offspring told Harper's Bazaar in 2017 that her father always pushed his family to be their best, and particularly when it came to physical activity: "We'd get up really early, like 6 a.m. and do 20 sit-ups and push-ups, practice our shot put — he wanted us to be really good at shot-putting for some reason — learn how to throw a punch, and practice golf."

It took nearly a decade for Sylvester Stallone and Jennifer Flavin to go from complete strangers to husband and wife. Yes, despite going their separate ways for two years — a period in which the former cozied up to another model, Janice Dickinson — the pair managed to patch things up enough to set a wedding date. And while they got hitched in style, the ceremony was a little more low-key than you would expect from one of Hollywood's premier action heroes.

As People reported at the time, Stallone and Flavin exchanged their vows in May 1997 in front of approximately just 12 of their nearest and dearest, firstly at a civil ceremony at London's The Dorchester Hotel and then at a chapel at Oxfordshire's Blenheim Palace. Guests included Robert Earl, the founder of the Planet Hollywood restaurant chain Stallone invested in, and Flavin's siblings. Despite his past indiscretions, the "Demolition Man" star appeared to get the Flavin family's seal of approval. One of Flavin's brothers shared with People, "When they got back together it seemed they knew what they wanted. She knows that Sly is pretty much settled down. He's getting older too, you know." Patrick, meanwhile, was more than happy to tell the same magazine that his sister was on cloud nine.

Sylvester Stallone and Jennifer Flavin welcomed their second child, Sistine Stallone, into the world in 1998 before completing their family unit four years later with the arrival of third daughter Scarlet Stallone. And just like their older sister Sophia Stallone, the two youngest daughters appear to be thriving.

According to Page Six, at the age of 17, Sistine signed a deal with IMG Models, going on to make her runway debut in Paris a year later. Scarlet has also dabbled in the same world while simultaneously killing it on the running track as one of her school's star athletes. And in 2017, all three Stallone daughters were given the honor of escorting various award winners on and off the stage in their joint roles as Miss Golden Globe.

In a family interview with Harper's Bazaar later that same year, Sophia discussed how close all three sisters are: "Sometimes siblings can get into rivalries, but we've been nothing but support to one another." Flavin, meanwhile, revealed that although her daughters are as thick as thieves, they each have their own distinct personalities. "They're all totally different," she said. "But I expect them all to work hard and do well with whatever they're good at."

Asked what the secret to their marriage was by their own daughters on their podcast "Unwaxed," both Jennifer Flavin and Sylvester Stallone agreed on independence. And the former was particularly proud of the fact that she does not have to rely on her husband for financial support. The former model said, "I think that was one of the biggest things that helped our marriage because I made my own money. I paid my own bills and I did very well. So I didn't need Sly's money. I didn't need to be in a movie of his, I'm not an actress. I didn't need any of his friends." And while many A-list stars make a point of drafting up a prenup when they decided to get married, TMZ reported Stallone and Flavin decided against taking that legal step when they got hitched in 1997. 

In the aforementioned podcast episode, Stallone revealed that he never tried to stifle his wife's ambitions. "I think to have a happy marriage you have to let people follow their natural inclinations. Some people don't want to work, some people need to work. That was her thing. She's been on her own since she was 12, 13, so I thought, 'You know what? Just let her go.'" And just letting her go has been a boon to her bank account: As W Magazine noted, her skincare company, Serious Skin Care, had raked in $1 billion by 2010.  

Sylvester Stallone and Jennifer Flavin may have a modern setup when it comes to their financial affairs, but when it comes to their daily routines, they are fairly old school. On an episode of Sophia and Sistine Stallone's "Unwaxed," Flavin shared the she pretty much waits on her husband hand and foot.

The Serious Skin Care founder said, "I do everything from the minute we wake up, to getting him coffee, bringing it to him in bed, bringing him cookies in bed every morning, then going downstairs. ...  I make you breakfast in the morning, and then I make sure everything is great for you for the day, I go through your schedule." She also noted that her husband still cracks her up every morning all these years later. On a separate episode of "Unwaxed," Flavin and Sylvester's daughters pointed out that laughter seems to be the foundation of their parents' relationship — and a solid one at that.

As for what else Sylvester brings to the table? The "Daylight" star freely admitted, "I just aggravate the hell out of her. I don't really know what I do for her." He went on to acknowledge how much she does for their family and how much she means to him, quipping that he wouldn't think twice about putting himself in front of a moving train to save her. "I think she's fantastic. She's an amazing woman," he said. "I tell her that every day. I don't know how she holds it together."

Sylvester Stallone and Jennifer Flavin's marriage looked to be in a good place in May 2022 when they each gushed about each other on social media to commemorate their silver wedding anniversary. But little did their Instagram followers — or the rest of the world, for that matter — know what was just around the corner.

Alongside ten loved-up Instagram photos of himself and his wife, the "Tango and Cash" star wrote, "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!"

In return, Flavin uploaded her own photographic trip down memory lane. She wrote (via People), "Thank you for always keeping me laughing, loving and protecting our beautiful family! Our marriage keeps getting better every year! I can't wait to spend the rest of our lives together!" Within just a few months, however, their apparent state of wedded bliss had turned distinctly sour.

Rumors that things weren't as picture-perfect as Sylvester Stallone and Jennifer Flavin had purported started to circulate in August 2022 with the reveal of some ink. As the Daily Mail reported, the former got tongues wagging when he was spotted getting a bicep tattoo of the latter's face covered up with a rendering of his dog.

Shortly after, Flavin fanned the flames even higher when she uploaded a mother/daughters snap on Instagram captioned, "These girls are my priority. Nothing else matters. The four of us forever." A spokesperson swiftly insisted that there wasn't any disharmony in the household. But within a few days this denial had been blown out of the water.

In a statement to People, Flavin said, "I'm sad to announce that after 25 years of marriage I have filed for divorce from my husband Sylvester Stallone. ... I know we are both committed to our beautiful daughters. I ask for privacy for our family as we amicably move forward." Her husband, meanwhile, simply responded, "I love my family. We are amicably and privately addressing these personal issues."

So what could have caused the once-happy couple to call it a day just months after celebrating 25 years of marriage? Well, in the divorce petition filed by Jennifer Flavin that was obtained by People, it was alleged that Sylvester Stallone had "engaged in the intentional dissipation, depletion and/or waste of marital assets which has had an adverse economic impact on the marital estate."

If you're wondering what on earth that all means, then it's essentially another way of saying that the "Escape Plan" star had a habit of overspending. As a result, Flavin was also reportedly demanding, as the petition put it, "unequal distribution of the marital assets in her favor."

The pair were said to have estimated a net worth of several hundreds of million dollars during their quarter-century together. And their real estate portfolio included an unspecified property in California and a Palm Beach waterfront mansion that Flavin was asking for exclusive residence of. Earlier in the year, the couple had put another of their houses, an eight-bedroom pad in Beverly Park, Los Angeles, on the market. As TMZ reported at the time, record industry savior Adele snapped it up for a cool $58 million.

Listeners of "Unwaxed," the podcast co-hosted by sisters Sophia and Sistine Stallone, might have been less surprised to hear about their parents' divorce proceedings. For just a year earlier, Jennifer Flavin had admitted to her daughters in an interview that her and Sylvester Stallone's relationship wasn't without its difficulties. When discussing the ups and downs of marriage, the former model said, "Sometimes fighting is good because you get out a lot of stuff that you've been holding in." Flavin also shared with her daughters that she usually encourages her friends to give their own relationships a second chance before heading down the divorce road. "If they're just always arguing, I go, 'This time shall pass and you guys are going to get through this,'" she said.

In the same podcast episode, Flavin advised her daughters to live with any prospective husbands before saying "I do" to really see if they are compatible and if they can actually work as cohabitants. "I am very A type and my husband is not A type," she shared. "He's very messy, I'm not. So, can I live with messy, things like that."

According to Radar, the Stallone daughters were in their mom's corner after the divorce news.

Following the news that Jennifer Flavin had filed for divorce from her husband of 25 years Sylvester Stallone, speculation inevitably bubbled up regarding the root cause. And according to TMZ, it was the adoption of a Rottweiler named Dwight.

Yes, various sources claimed to the gossip site that the couple had come to blows over the pooch, with the "Creed" star believing it would give his family an extra level of protection and his wife not wanting to go anywhere near it. But Stallone later insisted to TMZ that the canine had nothing to do with their fallout: "We did not end the relationship on such a trivial argument. We just went in different directions. I have the highest respect for Jennifer. I will always love her. She's an amazing woman. She's the nicest human being I've ever met."

The action hero also cleared up all the drama over his dog tattoo. Apparently, things went awry while he was getting one of his two existing tattoos of Flavin fixed, so the artist reworked it entirely and turned it into an illustration of Butkus, his late dog. 

In a comeback that Rocky Balboa would be proud of, Jennifer Flavin and Sylvester Stallone's relationship took yet another new direction, somehow getting back on track just a month after the former announced she was filing for divorce. The pair shocked the tabloids once again in September 2022 when they revealed that they'd reunited before the ink on any legal documents had even dried, and decided to put a stop on the divorce proceedings entirely. A spokesperson for the seemingly indecisive couple told Page Six that the couple ironed things out. "They are both extremely happy," the rep said. 

Stallone had hinted that the situation may have changed just a few days earlier with an Instagram throwback photo of himself holding hands with his estranged wife. The picture's simple caption, "Wonderful," led many followers to believe that there was still hope for the couple who'd only just celebrated their 25th wedding anniversary. Just weeks later, outlets including People noted that the two were out and about together in NYC, looking happy and wearing their wedding rings.