How Sylvester Stallone’s Marriage to Jennifer Flavin Was Nearly Doomed by ... FedEx?!

The <em>Rocky</em> star broke up with Jennifer Flavin at one point via a six-page handwritten letter he had delivered via FedEx. (Photo: Getty Images; Illustration: Imma Almourzaeva)
Sylvester Stallone and Jennifer Flavin almost didn’t make it down the aisle. The Rocky star broke up with the model at one point via a six-page handwritten letter that he had delivered via FedEx. (Photo: Getty Images. Image: Imma Almourzaeva)

Sylvester Stallone and Jennifer Flavin mark their 20th wedding anniversary on Wednesday, May 17, but there was almost no wedding — and no Sophia, Sistine, or Scarlet (aka their model daughters).

Back in 1988, the Rocky star, then 42, had a chance meeting with the aspiring model, who was just 19, at a Beverly Hills, Calif., restaurant, and they started dating. Now, Sly wasn’t a choir boy — he was twice divorced with a roving eye — but a May-December romance was in full swing. Until it wasn’t.

Special delivery … not!

Fast-forward to March 11, 1994, when Flavin received a FedEx package with a “Dear Jennifer” letter in it. Instead of breaking up with her face-to-face — or even over the phone — the actor sent a six-page handwritten letter unceremoniously dumping her after more than five years together.

Yes, years before the rude Post-it parting, insensitive 27-second phone call castoff, or horrible text divorce, the two-time Academy Award nominee (and grown man!) dumped Flavin via overnight delivery. People magazine interviewed Flavin during the height of the drama, and she talked about receiving the sloppily written letter. “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.”

Sylvester Stallone and Jennifer Flavin met in 1988 — and by 1991, they were hot and heavy.
Sylvester Stallone and Jennifer Flavin met in 1988 — and by 1991, they were hot and heavy. But his idea of committed was different from hers. (Photo: Ron Galella/WireImage)

However, Flavin’s interview got more interesting than talking courier companies. She went on to tell the mag what she later learned from her agent was the real reason behind Sly’s lazy breakup letter: Sly was having an affair with another model, Janice Dickinson, and she had given birth to a daughter, Savannah (Sly loves those S names), who was widely reported to be his. He wanted to be free to pursue that relationship. Flavin called the drama “every woman’s worst nightmare,” especially after Sly had recently gushed about her to the Toronto Sun, saying, “Jennifer has made all the difference” in his life.

For the record, Sly had also described his romance with Flavin in another interview as one with “no strings attached” — and Jennifer herself told Cosmopolitan, “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.”

Their year apart (whew!)

Now, we know that Sly and Jennifer ended up back together the following year and had a very happy ending, but his “lost weekend” — in between their March 1994 breakup and reunion in the summer of 1995 — was action-packed. For starters, whatever he had going on with Dickinson was over by July when DNA tests proved he was not the father of her baby. But there were other models for Sly to date — and he did, starting with Austrian model Andrea Wieser, 22. That was followed by a public war of words with Richard Gere, who accused Sly of romancing his then-wife, Cindy Crawford. (Yes, that Cindy.) Oh, and there was an engagement: After seeing Sports Illustrated swimsuit model Angie Everhart, then 25, on a magazine cover, he had his people call her people (as celebs do!), and they were betrothed by April 1995, but it obviously didn’t last. Yes, this all happened in just over a year.

Sylvester Stallone and his one-time fiancee Angie Everhart in 1995.
Sly’s busy year apart from Jennifer Flavin (from March 1994 to the summer of 1995) included a brief engagement to Angie Everhart, who is pictured with the actor (in matching jackets) at a Planet Hollywood event in 1995. (Photo: Jim Smeal/WireImage)

Perhaps exhausted by his own shenanigans or realizing it was time to grow up, Stallone reconciled with Flavin in the summer of 1995. Suddenly a changed man — People magazine noted he had become an “impeccable” partner to Flavin — they quickly started their own family, welcoming daughter Sophia in 1996. When the baby needed heart surgery, they grew even closer.

Back together and going to the chapel

The pair decided to make things official on May 17, 1997, when they tied the knot in London — and it was a fancy affair. They first exchanged vows — with their healthy 9-month-old daughter in attendance — in the Penthouse Pavilion of the Dorchester Hotel.

Jennifer Flavin and Sylvester Stallone were married on May 17, 1997.
Jennifer Flavin and Sylvester Stallone were married on May 17, 1997. (Photo: John Carter/Rex/Shutterstock)

A car then took them — with Jennifer rocking an Armani dress — 60 miles away to to Blenheim Palace, the birthplace of Winston Churchill, where their marriage was blessed in a chapel. They spent their first night as newlyweds at the palace before jetting off to Ireland for their honeymoon.

“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,” Sly said in a statement.

Surrounded by women — and loving it

Scroll through Stallone’s Instagram and you’ll see that today he is a family man. Now 70, the star often documents the school pickups, sporting activities, and at-home silliness of the pair’s three girls, who all followed in mama’s footsteps and are models. (He lost a son from his first marriage, Sage, to heart disease in 2012, likely making him even more of a doting dad. He also has a son, Seargeoh, who is autistic, from that relationship.)

Sylvester Stallone and his ladies — Sistine Stallone, Scarlet Stallone, Sophia Stallone, and Jennifer Flavin.
Sylvester Stallone and his ladies — Sistine Stallone, Scarlet Stallone, Sophia Stallone, and Jennifer Flavin — celebrating the girls’ Harper’s Bazaar cover on April 26. (Photo: Stefanie Keenan/Getty Images for Harper’s Bazaar)

He opened up about his marriage in a 2010 interview with the Telegraph, saying that his family life and home are the opposite of his testosterone-heavy upbringing — and movies from Rocky to Rambo.

“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 learnt 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.”

After the interviewer brought up some of his past relationships (including his brief marriage to second wife Brigitte Nielsen), Stallone shared his outlook on his life and love, saying, “I consider my life 10 percent on target, and 90 percent mistakes.” After a beat, he added, “But those 10 percent counted.”

And these past 20 years of marriage have counted too.

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