A Timeline of Sylvester Stallone and Jennifer Flavin's 26-Year Marriage

The couple first crossed paths in 1988 at a West Hollywood restaurant, according to People. Stallone was 42 years old and a two-time divorcé (he was married to Sasha Czack from 1974-1984 and Brigitte Nielsen from 1985-1987). Flavin, meanwhile, was a 19-year-old model from San Fernando Valley, CA.

"I'd come over, and we'd watch a movie, cook dinner, goof around with the dog or walk on the beach," Flavin told People in 1994, describing the early days of their relationship. The pair made their red carpet debut as a couple in 1990.

Flavin was dumped by the "Rocky" star via a hand-delivered FedEx letter in March 1994. She was gearing up to join Stallone in Florida, where he was filming "The Specialist." When Stallone begged her to delay her visit, she chalked it up to nerves; however, Flavin soon discovered her boyfriend was being joined by model Janice Dickinson and her newborn daughter, who was rumored to be Stallone's child.

In a 1994 interview with People, Flavin said she "cried a lot" and was "disappointed" with the way Stallone handled their breakup. "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. "And I cleaned my apartment about five times. I had so many pictures and things to get rid of."

Stallone and Flavin exchanged nuptials in a civil ceremony at London's The Dorchester Hotel. They were joined by a very small group of friends and family for an intimate chapel ceremony at Blenheim Palace in Oxfordshire, People reported at the time. In a statement obtained by People, Stallone said, "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."

May 2022 marked the couple's 25th wedding anniversary. Stallone celebrated the milestone with a heartfelt tribute to his wife on Instagram. "Happy 25th anniversary to my amazing wife," the actor captioned a slideshow of family photos from over the years. "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!"

In August 2022, it was rumored that the Hollywood couple was headed to splitsville. People confirmed the news and reported that it was Flavin who was filing a petition "for dissolution of marriage and other relief."

"I'm sad to announce that after 25 years of marriage I have filed for divorce from my husband Sylvester Stallone," she told the outlet at the time. "While we will no longer be married, I will always cherish the more than 30-year relationship that we shared, and I know we are both committed to our beautiful daughters. I ask for privacy for our family as we amicably move forward."

A month later, in September 2022, the couple requested for the judge to abate their divorce proceedings on account of reconciliation. "They decided to meet back up at home, where they talked and were able to work out their differences," Stallone's rep told Page Six. "They are both extremely happy."

In an interview with the Sunday Times, the "Rambo" star described the past few months as "a very tumultuous time." "There was a reawakening of what was more valuable than anything, which is my love for my family. It takes precedence over my work, and that was a hard lesson to learn," he told the publication.

In an episode of "The Family Stallone" (via People), Stallone said he's looking forward to slowing down and enjoying life with Flavin and their girls. "Jen and my careers have been so crazy for so long," he explained in an interview shown in the show. "I'm looking forward to a new chapter of life, slowing down for a change to spend some time with my girls. I won't be around forever, and I certainly want to leave them with fine thoughts of their father — that he did the best he could to make their life as fruitful as possible."

Flavin added: "It's like we can start living again."