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Actor Sylvester Stallone admitted that he was a "coward" for his questionable attempt to break up with his then-girlfriend, now his wife, Jennifer Flavin in 1994. The Hollywood star sat down with Sean Hannity for the debut episode of Fox Nation's monthly interview series called Sean to share that he once sent Flavin a breakup letter via FedEx. He called himself a coward for not communicating his feelings in person, adding:
"That's the most insincere breakup you can get... You put it down in words 'cause you don't have the guts to do it face to face."
He also admitted that he sent a letter instead of speaking his feelings out loud at the time because a part of him didn't want to split up. The other reason, he added, was because of his "history with relationships," which the movie star described as "an abomination."
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While Sylvester Stallone had been candid with his lapse in judgment at the show, it wasn't the first time his FedEx apology letter came out in conversations. Flavin spoke about it with People in 1994, saying that it was a "six-page handwritten letter, in pen."
Sylvester Stallone and Jennifer Flavin did break up at the time. However, they reportedly got back together the following year and eventually tied the knot in 1997.
Sylvester Stallone and Jennifer Flavin's relationship timeline explored
The Hollywood couple have been married for around 27 years, and here's a closer look at their relationship over the years.
1988
Stallone and Flavin met for the first time in 1988 when she was 19 and he was in his early 40s and had been married twice with children. She told People in 1994 about that time, saying she was visiting Hollywood with a friend and happened to be at a Beverly Hills restaurant where the Rocky actor was also present.
June 1990
They made their relationship red carpet official at the Los Angeles gala, with Stallone in a classic tuxedo and wire-rimmed glasses and Flavin sporting a plunging black gown and dangly earrings.
March 1994
After six years together, Sylvester Stallone sent Jennifer Flavin a breakup letter via Fed-Ex. She called it a "pretty sloppy" six-page letter, and a few days later, she found out why the movie star dumped her. It turns out that Stallone had been having an affair with supermodel Janice Dickinson. That relationship also ended, but not after the issue of a possible love child of Stallone and Dickinson came out.
1995
A year after their breakup, Stallone and Flavin found a way back to each other. It happened after Stallone found out that he wasn't the biological father of Dickinson's baby after doing a paternity test.
March 1996
Stallone and Flavin started their own family together. They welcomed their first baby on August 27, 1996. They named their baby girl Sophia Rose.
May 1997
A year after their first baby's birth, the couple decided to get married in a civil ceremony. They had a wedding at The Dorchester Hotel in London but later had a chapel ceremony. They picked Blenheim Palace in Oxfordshire for their chapel wedding. Only their close family and friends were there.
June 1998
Sylvester Stallone and Jennifer Flavin welcomed a new addition to their family. Their second daughter, Sistine Rose, was born on June 27, 1998.
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May 2002
On May 25, 2022, their third daughter Scarlet Rose was born.
May 2022
They celebrated their 25th wedding anniversary, and Sylvester Stallone took to Instagram to praise his wife. In the caption of a photo carousel of themselves together, he 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!"
Flavin also thanked Stallone for "loving and protecting our beautiful family" under her own snapshot collection shared on social media.
August 2022
Three months after sharing sweet words during their 25th anniversary, Flavin filed for divorce.
September 2022
Sylvester Stallone and Jennifer Flavin were photographed holding hands amid their divorce. The star shared the picture on his Instagram, which he captioned "Wonderful..."
While it was unclear when the photo was taken, the Armor actor sharing it on social media sparked reconciliation rumors.
October 2022
Stallone and Flavin were photographed arm-in-arm while walking around downtown Manhattan and later for a date night at the Polo Bar. Photos of them also reportedly showed both Stallone and Flavin still wearing their wedding rings.
May 2023
Their reality TV show, The Family Stallone, came out on Paramount+. They attended the premiere in coordinating all-black outfits in New York City.
February 2024
The Family Stallone returned for a second season, featuring the Tulsa King actor telling his daughters that he and Flavin are leaving California for Florida.
May 2024
Sylvester Stallone and Jennifer Flavin celebrated their 27th wedding anniversary. He shared pictures from their 1997 London wedding on Instagram to celebrate, calling Flavin the "love of my life" in the caption.
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