Sylvester Stallone Finally Lets Cameras into His Private Family Life after Wife of 25 Years Filed for Divorce

• Before tying the knot, Sylvester Stallone ended his relationship with Jennifer Flavin unexpectedly—through a letter.
• After a quarter-century of marriage, Flavin once filed for divorce from her husband.
• In a surprising turn of events, Stallone has reportedly decided to prioritize his family over his iconic Hollywood career.

After years of shying away from sharing his personal life with the public, Sylvester Stallone is reportedly opening up about his family in a new reality show.

This news surprises many, as the actor has been known to keep his private life under wraps. The decision to participate in the show comes on the heels of a tumultuous year for Stallone’s marriage.

Sylvester Stallone with Jennifer Flavin in 1990 at Spago’s Restaurant in Hollywood, California. | Source: Getty Images

In 2022, Stallone’s wife, Jennifer Flavin, filed for divorce, marking a difficult time for the couple. However, the couple has rebuilt their relationship, and it was not the first time.

Nearly 30 years ago, Stallone ended his relationship with Flavin via a letter, a detail that has resurfaced in light of recent events. The “six-page handwritten letter” was the actor’s way of dumping his then-girlfriend.

Actor Sylvester Stallone with wife Jennifer Flavin attend an event on October 11, 2010 in Hollywood, California. | Source: Getty Images

The letter and other revelations have come to light again since Stallone changed his stance on his desire for privacy. With “The Family Stallone” airing in May 2023, he is now willing to give fans a glimpse into his personal life.

Before Their Marriage, Sylvester Broke up with Jennifer via a Letter

Flavin and Stallone’s relationship has been anything but a smooth ride. The couple, who have been married for over 20 years, had a tumultuous start to their romance.

Actor Sylvester Stallone is spotted with Jennifer Flavin on August 26, 1988. | Source: Getty Images

Before they were wed, the couple had been dating for nearly six years. However, their relationship took a sour turn when Stallone decided to end things with Flavin in an unexpected manner.

According to Flavin’s version of events, Stallone broke up with her in a letter sent via FedEx on March 11, 1994. The letter was, in her words, “pretty sloppy,” but the message was clear: Their relationship was over.

She was completely blindsided and stated they had already planned a future and even discussed having kids together.

Sylvester Stallone and girlfriend Jennifer Flavin on a skiing trip, in 1995. | Source: Getty Images

Flavin revealed the heartbreaking truth about the end of her relationship, recalling that Stallone was in Florida for a new movie when he suggested she postpone her arrival.

Unbeknownst to her, Stallone had already moved on and was with another woman, model-photographer Janice Dickinson. Flavin cried a lot and cleaned her apartment five times after the breakup.

However, what hurt the most was how the actor ended their relationship. She expressed her disappointment in Stallone for ending things via a letter that left no room to talk.

Actor Sylvester Stallone and Jennifer Flavin, spotted together in 1997. | Source: Getty Images

Despite the tears, setbacks, and challenges, the couple eventually reconciled and built a life together. They tied the knot in 1997 at London’s Dorchester Hotel.

When Jennifer Filed for Divorce after 25 Years of Marriage

On August 24, 2022, Flavin initiated divorce proceedings against Stallone in Florida and asked to continue residing in their Palm Beach home. In addition, she alleged that Stallone was concealing shared assets and requested to retain her maiden name.

Actor Sylvester Stallone with wife Jennifer Flavin attend an event at Grauman’s Chinese Theatre on October 11, 2010 in Hollywood, California. | Source: Getty Images

On August 29, Stallone filed a response in which he refuted various accusations and appeals made by Flavin. Still, he agreed to some of her requests, such as her wish to keep her name.

It was also reported that Stallone had covered up a tattoo of his wife on his bicep. The tattoo was replaced with a portrait of his character Rocky’s bull mastiff, Butkus. The new ink caused fan speculation about trouble in the couple’s marriage.

However, Stallone’s rep attempted to downplay the situation by stating that the change was intended to refresh the tattoo but did not go as planned. The statement concluded that the actor loved his family.

Sylvester Stallone with Jennifer Flavin on October 06, 2022 in New York City. | Source: Getty Images

After the initial shock of the divorce filing and tattoo cover-up, Stallone and Flavin’s relationship seemed irreparably damaged. But despite their differences, the couple couldn’t resist the pull towards each other.

As one of their daughters put it, they are “polar opposites” who “literally cannot live without one another.” And it turns out she was right. Flavin admitted that her daughter’s words were true in a heartwarming turn of events.

According to an exclusive report by Page Six, the couple was able to work out their differences, leading to their decision to reconcile.

The spokesperson for Stallone confirmed the news and said the couple is content. The order of abatement, which was filed aimed to put a hold on divorce proceedings, clearly indicates the couple’s desire to give their marriage another chance.

Sly Finally Chooses Family over Career

In a recent interview, Stallone opened up about his regrets and shared he was trying to make amends. The action star revealed that he often put work ahead of his family in the past and called it “a tragic mistake which won’t happen again.”

Jennifer Flavin and Sylvester Stallone with their daughters Scarlet, Sophia and Sistine attend a movie premiere on August 15, 2012 in Hollywood, California. | Source: Getty Images

Stallone acknowledged that he missed spending quality time with his family, particularly his daughters, when they were younger. Now, he’s committed to being there for them more.

This newfound perspective is one of the reasons why Stallone agreed to do the reality show that he’s received criticism for.

While his daughters admit “he’s the last person that wanted to do this,” the father is going ahead with it for his girls. He explained:

“Everyone goes, ‘I wish I’d shown love more’ or ‘I wish I’d spent more time with the kids.’ I’m riding that boat. That’s one of the reasons I wanted to do the reality show.”

Sophia Rose Stallone, Jennifer Flavin, Sylvester Stallone, Scarlet Rose Stallone and Sistine Stallone together on November 01, 2019 in Beverly Hills, California. | Source: Getty Images

The “Rocky” star’s decision to launch a reality show has garnered mixed reactions from onlookers, with some slamming and others applauding the move. Many fans were excited to see inside the family’s world, remarking:

“This looks awesome. Just good old fashioned, heartfelt material with really sweet, interesting, funny people.”

Sylvester Stallone, Jennifer Flavin and their daughters Sistine Stallon, Scarlet Stallone and Sophia Stallone at the 74th Annual Golden Globe Awards on January 8, 2017 in Beverly Hills, California. | Source: Getty Images

Another online user was amazed at how well Flavin blended in with her daughters, while someone else expressed enthusiasm for the heartfelt and funny material. They noted:

“So basically, The Kardashians, but less drama, less glitter, less glamor, [fewer] silicons—but more respect, fun, and smarter? COUNT ME IN.”

However, many people challenged the actor’s motives, comparing the show to the Kardashians. Some fans were worried and questioned the actor’s choices. One netizen asked: “Really? Rambo wants to be like the Kardashians? Really?”

Despite the criticisms, Stallone remains optimistic about the show, saying that it’s a chance for his kids to see him in action and for him to see them in action.

Subscribe to AmoMama on Google News!