What would you do if the person you loved had an affair and then broke up with you through
a FedEx letter?
Well, that’s exactly what Sylvester Stallone did to Jennifer Flavin.
The pair were known for their on-and-off-again romance in the early ‘90s, which has since
blossomed into a 25-year-long marriage.
Although their union started off a bit rocky, Jennifer has stood by her husband through
it all.
This was Sylvester’s fifth engagement and third marriage, but we’ll get into all of
that later.
From their first encounter to the births of their three children, here's everything to
know about these lovebirds.
It was 1988 in Beverly Hills where Sylvester Stallone and Jennifer Flavin met.
She was a 19-year-old Valley Girl visiting Hollywood with a friend.
They decided to go to a restaurant and that is where she and Sylvester crossed paths for
the first time.
The actor was 41, had already been married twice, and was a father of two sons.
Stallone was at the height of his career and had a reputation as a bit of a playboy.
Despite his rep and their 22-year age difference, the two felt something special was there and
immediately started dating.
Jennifer and Sylvester went on to date for the next 6 years and it appeared to be a very
happy time.
Then, disaster struck and they split up.
Was FedEx involved in their split?
In a way, yes.
Sylvester sent Jennifer a 6-page letter in which he dumped her.
“He sent me a handwritten letter, in pen.
It was pretty sloppy.
I was disappointed.
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,” she said.
Flavin didn’t learn the real reason the actor dumped her until a few days later when
her agent called to tell her.
Stallone had been having an affair with supermodel, Janice Dickinson
Janice was pregnant, so the actor proposed to her almost right after ending it with Jennifer.
They were together for less than a year.
The news of the pregnancy obviously devastated Flavin.
And she didn’t even know about the affair.
She and Stallone spoke about having children, about when they were going to get pregnant
and were already picking names that they liked.
Awww….
Apparently, Flavin knew Stallone had a history of extra-marital affairs.
"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,"
she said.
Sylvester found out via a paternity test that he was not the father and promptly ended his
relationship with the supermodel.
From there, he was briefly engaged to model Angie Everhart (https://www.youtube.com/watch?v=_yI7_k-zHU0
0:04) before rekindling his romance with Jen.
In case you’re not keeping up, this was all within one year after the actor’s split
from Jennifer!
It seems that the love Stallone and Flavin shared was too great to let go.
In 1995, the model gave the actor a second chance.
A year later, they welcomed their first child together, Sophia (https://www.youtube.com/watch?v=ROPVS289YCA
0:08) Rose Stallone.
Shortly after her birth, the little girl was found to have a hole in her heart and needed
surgery.
Thankfully, it was successful and little Sophia was back home with her parents soon after.
A year after they grew their family, the couple had a low-key wedding with only a dozen close
friends and family members.
Despite their rocky past, Flavin’s older brother, Mitch (https://www.youtube.com/watch?v=w6vRW3TdRuc
0:07) said, “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."
At the time, the Rambo (https://www.youtube.com/watch?v=Ee3dh0CvXWY 0:06) actor was 50 and she was 28.
In 1998, the pair welcomed their second daughter, Sistine (https://www.youtube.com/watch?v=nr9dix9ViRI
0:01) Rose, and four years after that, their third child, Scarlet (https://www.youtube.com/watch?v=k0yEUq8OEKM
0:07) Rose.
In an interview, Flavin said Sophia is the child that most resembles her father.
"Like him, she has read nearly all of Shakespeare's books.
They have a very special bond; they think alike and even have the same gestures," she
revealed.
As we mentioned before, Sylvester’s three daughters with Jennifer weren’t his only
children.
His first wife was Sasha Czack (https://www.youtube.com/watch?v=apXvQb7lzw0 1:30), whom he married in 1974.
Their marriage was a difficult one and came crashing down, not once but twice.
The first time was when the actor walked out on her following Paradise Alley, four years
after getting together.
“I had discovered real fear for the first time.
Fear of losing what I had attained.
Before, I didn’t care.
I was broke.
I became a recluse.
But the most drastic change was my values.
I really became envious and coveted other people’s success.
I resented my family because of that comparison, and that’s when I began the affair.
I felt I was really slipping down,” he said.
Stallone began a public affair with Susan Anton.
When he and Susan broke up, and he started missing his wife and kids.
Before taking him back, Czack told the actor to get his personal demons and existential
crisis under control.
“She knew that if I came back at that time, eventually I would leave again.
In other words, there were too many loose ends.
Go out and solve the mystery,” he said.
While Sasha and Sylvester reconciled, their marriage didn’t outlast the 80s and they
divorced on Valentine’s Day 1985.
The reason behind their divorce was most likely the First Blood actor’s second wife.
While he was still married to Sasha, he met Brigitte Nielsen (https://www.youtube.com/watch?v=v15Tqx086JI
0:03).
An up-and-coming actress who was hoping to get a start in Hollywood.
She contacted Sylvester, who was 17 years her senior by sending him a provocative promo
photo of herself with a note.
It read, "My name is Brigitte Nielsen.
I'd really like to meet you.
Here's my number."
Stallone went to see Nielsen that same night.
He then divorced Czack, and married Nielsen shortly after.
Their union only lasted 19 months and the reason for their divorce was cited as irreconcilable
differences.
Ah, a Hollywood favorite.
“It was a horrible marriage.
Everybody looks at you as a villain.
After I left Sylvester, I kind of felt like I was blacklisted for a long time.
I am almost positive that had I not been in the public eye with this famous man, that
would never have happened,” Brigitte said.
A positive side to the decade-long marriage between Sasha and Sylvester were their two
sons, Sage (https://www.youtube.com/watch?v=-GdAJ-jcvSQ 0:28) Moonblood and Seargeoh (https://www.youtube.com/watch?v=apXvQb7lzw0
0:28).
Tragically, Sage passed away at the age of 36 in 2012.
Although many speculated that drugs were the cause of his death, no drugs were found in
Stallone's body other than over-the-counter pain medication.
He died of atherosclerosis, which brought on a heart attack.
Sylvester later made a public appeal for people to stop speculating about the drugs being
the cause of his son’s death.
"When a parent loses a child there is no greater pain.
Therefore, I am imploring people to respect my wonderfully talented son's memory and feel
compassion for his loving mother, Sasha, because this agonizing loss will be felt for the rest
of our lives.
Sage was our first child and the center of our universe, and I am humbly begging for
all to have my son's memory and soul left in peace," he said.
How devastating is that?
Jennifer was of course standing right by her husband’s side through this tragedy.
The couple managed to keep their lives going forward through this incredibly difficult
loss.
Last year, the actor celebrated his 75thbirthday.
He shared a sweet photograph of himself, his wife, and their daughters on Instagram, captioning
the post.
“My wonderful family is the best birthday present I could ever receive."
In May 2022, the couple also marked 25 years of marriage.
They sold their $110 million Los Angeles estate seeking a quieter life in Palm Beach, Florida.
Stallone and Flavin posted respective tributes to each other on Instagram to celebrate their
milestone, wishing for another 25!
"Happy 25th anniversary to my amazing wife.
It took me 19 years to realize she’s always right.
I realized that Jennifer has a knack for making incredibly erudite, wise, smart decisions.
I always leap without looking.
There are not enough words to describe what this incredibly selfless dedicated, patient,
woman has meant to our lives, and I only wish there could be another 25!
Thank you, sweetheart,” he said.
Well, can’t help but wish them the same thing!
Jennifer posted an equally sweet tribute to her hubby.
"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!
I love you so much and we will be spending the next 25-plus years together!
Keep me laughing and I'm yours for the rest of my life," she said.
Well, isn’t laughter one of the secrets to a long marriage?
Despite their difficult start and all the obstacles they had to endure over the years,
Sylvester Stallone and Jennifer Flavin have managed to have over three decades together.
This duo seems to have found the right one for each other, continuing to have a beautiful
marriage.
We look forward to seeing what they have coming next, and we hope that they’ve healed as
much as possible from the difficult loss of Sage Moonblood Stallone.
Let us know in the comments below what you thought the most difficult thing was in this
couple’s journey.
Until next time, this has been Rumour Juice.