Sylvester Stallone has been a staple figure in the world of Hollywood for nearly 50 years! There are only a select few actors in the industry that have managed to have a career as extensive as Stallone's, which is the very reason why he is considered to be one of the best. In addition to his professional success, appearing in some of the biggest movies, Sylvester Stallone has also had massive success in his personal life as well.
The actor has been married to his wife, Jennifer Flavin for 22 years now! This is not only a rare number to hear about in the entertainment industry, but throughout the outside world too. The duo share three beautiful daughters, who have all grown up right before our very eyes. Despite having a long and happy marriage, Sylvester and Jennifer had their fair share of ups and downs. Here is everything we know about the "rocky" relationship these two once shared!
A True Hollywood Love Story
Sylvester Stallone and Jennifer Flavin had first met at a West Hollywood restaurant way back in 1988. Despite Sylvester being 23 years Flavin's senior, the two felt something special at the time and began dating shortly after. While Stallone was already an established actor in Hollywood, Jennifer was just starting her career out as a model.
While the whole model meets actor formula is played out quite a lot in the entertainment industry, these two have quite the story to tell! After having appeared in hit films such as "Rocky" and "First Blood" in the late 70s and 80s respectively, Stallone was at the height of his career, but could he be tied down?
Despite Jennifer's efforts to turn the Hollywood playboy into a family man, things didn't start off as easily as she would have liked. While the couple has been happily married for 22 years, after having dated for over 30, and share three beautiful daughters, their happily ever after did, in fact, take some time.
When Things Got Rocky For "Rocky"
As mentioned, the duo share quite an age gap, however, neither of them have ever let their difference in age truly get in the way of their relationship, or at least they tried! In 1991, Stallone revealed that when he and Jennifer are together, "it is wonderful", however, when the two are separate, it's "no strings attached". The duo managed to date on and off for nine years before officially sealing the deal, however, those nine years weren't easy.
Jennifer revealed that she and Sylvester spent 5 of the 7 days of the week together, and while she believed he wasn't a "cheating dog" at the time, she was well aware that he was a man 23 years older than her and wanted to have his fun while he could. While the relationship itself is not at all a conventional one, it worked for the duo, but not for long.
Sylvester had begun to date model Janice Dickinson in 1994 and dumped Jennifer Flavin through a six-page letter delivered via FedEx. Flavin described the letter as "sloppy". While nobody truly knows why Sylvester decided to up and leave for a year, it appears as if he realized what he had truly lost.
A Second Comeback Story
Prior to dating Jennifer, Stallone had already undergone two public and messy divorces that left his "battered", so it was only fitting for the actor to experience a second go at a comeback, however, this time around, it wasn't about his career, but his love life.
After having dated around from 1994 to 1995, Stallone encountered one failed relationship after the next, including his fling with Janice Dickinson. While Sylvester wanted a "no strings attached" relationship, the actor would soon discover that what he had left behind was probably the best thing that was ever going to happen to him. Come 1997, and Sylvester Stallone and Jennifer Flavin had rekindled their romance and finally decided to tie the knot.
"Jennifer has made all the difference", Stallone said to the Toronto Star, proving that his rocky relationships during the duo's break were not a good fit for him. As most bad things pass, this did too! The couple celebrated their love at a lavish 1997 wedding surrounded by their closest friends and family, making it clear that these two were meant for one another.
The couple has since gone on to have three daughters together, Sistine, Sophia, and Scarlet, and Sylvester couldn't be happier! The actor revealed how in love with his life he is and how he owes it all to Jennifer. "I’ve never had more fun. I learned that from my wife. It took me 19 years to realize she’s always right", Stallone said, and truer words have never been spoken!