Sylvester Stallone and Jennifer Flavin's Relationship Timeline (2024)

Sylvester Stallone and Jennifer Flavin's relationship has been rocky — but they aren't giving up.

In August 2022, after 25 years together, Flavin filed for divorce from her movie star husband. However, she called off the divorce a mere month later.

"When Jen filed for divorce, she felt she had no option. She felt unheard and was very frustrated," a source told PEOPLE. "[Sylvester] always wanted to work things out. They love each other. They want to keep their family together."

The couple first met in 1988 at a restaurant in Beverly Hills, California. They went on to have an on-and-off-again romance until they married in 1997.

From their wedding in England to the births of their three children, here's everything to know about Sylvester Stallone and Jennifer Flavin's relationship timeline.

1988: Sylvester Stallone and Jennifer Flavin meet for the first time

Flavin was a 19-year-old Valley Girl visiting Hollywood with a friend when she and Stallone crossed paths for the first time at a restaurant in Beverly Hills. Stallone, who was in his early 40s at the time, had already been married twice and was a father to two sons, Sage and Seargeoh, with his first wife, Sasha Czack.

June 1990: Sylvester Stallone and Jennifer Flavin walk the red carpet together

The couple went public with their mutual affection at a Los Angeles gala in 1990. The pair was dressed to the nines; Stallone wore a tuxedo and wire-rimmed glasses while Flavin wore a black gown, black clutch and long, dangly earrings.

March 14, 1994: Sylvester Stallone breaks up with Jennifer Flavin Through a FedEx-ed Letter

Stallone sent a letter via Federal Express to Flavin in which he dumped her, bringing their almost six-year-long romance to an end. "He sent me a six-page handwritten letter, in pen," Flavin said to PEOPLE in a 1994 interview. "It was pretty sloppy."

Flavin did not learn the real reason Stallone dumped her until a few days later, when she found out from her agent at the Elite modeling agency that Stallone had been having an affair with supermodel Janice Dickinson.

In February, Dickinson gave birth to a baby girl who was widely rumored to be Stallone's child. "It hit me like a ton of bricks," Flavin told PEOPLE. "I had no idea this was going to happen. We talked about us having children, about when I was going to get pregnant. We were already picking names, marking down names that he liked and I liked."

Flavin said she cleaned her apartment five times, making sure to get rid of anything that reminded her of Stallone, including many pictures. "I was disappointed," she told PEOPLE. "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."

Stallone found out via a paternity test that he was not the biological father of Dickinson's daughter and promptly ended his relationship with the supermodel.

1995: Sylvester Stallone and Jennifer Flavin get back together

After Stallone found out he was not the father of Dickinson's baby girl, he found his way back to Flavin, who gave him a second chance.

August 27, 1996: Sylvester Stallone and Jennifer Flavin welcome their first baby

Stallone and Flavin welcomed their first child together, a baby girl whom they named Sophia Rose Stallone, in Miami, Fl. Sophia modeled throughout her childhood and went to USC, where she majored in communications. In 2017, Sophia told Harper's Bazaar that she dreams of one day owning her own business.

November 1996: Sylvester Stallone and Jennifer Flavin's infant daughter gets heart surgery

Shortly after her birth, Sophia was found to have a hole in her heart and needed surgery. Dr. Hillel Laks, chief of the division of cardiothoracic surgery and director of the heart and heart-lung transplant division at UCLA Medical Center, performed the surgery successfully and baby Sophia went back home with her parents safe and healthy.

In 1998, Stallone presented a check to the Heart of a Child Foundation, a Los Angeles-based nonprofit organization to benefit research on congenital heart defects, after going through that scary time, according to the Los Angeles Times.

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May 17, 1997: Sylvester Stallone and Jennifer Flavin get married

The couple wed in a civil ceremony at The Dorchester Hotel in London, followed by a chapel ceremony at Blenheim Palace in Oxfordshire. Only about a dozen close friends and family members attended the small wedding, including Flavin's sisters Julie and Trisha, Planet Hollywood founder Robert Earl and the couple's 9-month-old baby Sophia, PEOPLE reported in June 1997.

Flavin's older brother Patrick told PEOPLE that, before the wedding ceremony, "[Jennifer] said, 'I'm on cloud nine. I couldn't be happier.' She said, 'Sylvester is just beaming.'"

Despite their rocky past, Flavin's older brother Mitch 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."

June 27, 1998: Sylvester Stallone and Jennifer Flavin welcome their second baby

Stallone and Flavin welcomed their second child together, another baby girl named Sistine Rose, in Los Angeles, Calif. Sistine is now a successful model — she signed with IMG Models in 2015 when she was just 17. Her first runway show was Chanel at the Ritz in Paris in December 2016 where she met Karl Lagerfeld during her fitting backstage. "I don't think I've ever been so starstruck," Sistine told Harper's Bazaar.

May 25, 2002: Sylvester Stallone and Jennifer Flavin welcome their third baby

Stallone and Flavin welcomed their third child together, another baby girl whom they named Scarlet Rose, in Los Angeles, Calif. Scarlet has done some modeling with her older sisters, but her athleticism is what makes her stand out from the pack. By the eighth grade, Scarlet was already a star at running track at her school.

October 18, 2012: Jennifer Flavin explains the similarities between Stallone and daughter Sophia

In an interview and house tour with Paris Match in 2012, Flavin said Sophia is the child that most resembles her father.

"Like him, she has read nearly all of Shakespeare's books," Flavin said. "They have a very special bond, they think alike and even have the same gestures. Sophia is the love of his life."

November 9, 2015: Sylvester Stallone and Jennifer Flavin hold hands at the AFI Film Festival

The couple walked the red carpet together at the 2015 AFI Film Festival in Los Angeles, Calif.

January 8, 2017: Sylvester Stallone and Jennifer Flavin's three daughters are Miss Golden Globes

Sistine, Scarlet and Sophia had the honor of being "Miss Golden Globes" during the 2017 Golden Globes, meaning they escorted presenters and winners on and off the stage. The trio wore gorgeous matching black dresses — though they each brought their own special style to the table.

In 2017, the three sisters told PEOPLE that while Sistine's style is "chic and edgy," Scarlet's is "tomboyish" and Sophia keeps to classic, sophisticated styles. "Since I'm the oldest, I try to stay a bit more sophisticated and keep it simple," Sophia said. "Out of everyone I think Sistine can rock the complex, cool, rocker look."

August 14, 2018: Sylvester Stallone and Jennifer Flavin celebrate Flavin's 50th birthday together

Stallone, Flavin and their three daughters went out to Spago restaurant in Beverly Hills, Calif., to celebrate Flavin's big day. The family smiled and posed for photos together while Sistine, Scarlet and Sophia shined in colored mini-dresses.

May 10, 2019: Sylvester Stallone and Jennifer Flavin celebrate Sophia's college graduation

The couple celebrated their oldest daughter's graduation from the University of Southern California (USC). Stallone posted a picture of him and Sophia on Instagram for the big day, sharing his pride with his nearly 15 million followers.

"Our daughter SOPHIA graduates from USC !!!! An absolutely amazing day for us all. So proud!!! @sophiastallone" Stallone captioned the post.

January 25, 2021: Sylvester Stallone and Jennifer Flavin put their mansion on the market

Stallone and Flavin put their Beverly Park estate in Los Angeles — longtime home of the Stallone family — on the market for $110 million, listed by Hilton & Hyland. The couple was rumored to be leaving California for Palm Beach, Fl., at the time, according to Forbes.

May 17, 2022: Sylvester Stallone and Jennifer Flavin celebrate 25 years of marriage

Stallone and Flavin posted respective tributes to each other on Instagram to celebrate their 25th wedding anniversary.

"Happy 25th anniversary to my amazing wife," Stallone captioned a photo carousel of him and his wife. "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 accompanied her own snapshot collection with the caption "Happy 25th wedding anniversary to us! 🥰❤️❤️❤️ Thank you for always keeping me laughing, loving and protecting our beautiful family!"

She concluded, "Our marriage keeps getting better every year! I can't wait to spend the rest of our lives together!🥰❤️❤️❤️"

August 19, 2022: Jennifer Flavin files for divorce from Sylvester Stallone

Rumors about the state of Stallone and Flavin's marriage began swirling after he was seen covering up a tattoo of his wife's face with one of his dog Butkus in late August. Around the same time, Flavin posted an Instagram with her daughters that had the caption, "These girls are my priority ❤️ nothing else matters. The 4 of us forever🤍🙏🏻 #truth #family #forever."

Though a rep initially denied any trouble, on Aug. 19, Flavin filed a petition in a Palm Beach County, Florida court for "dissolution of marriage and other relief" from Stallone.

August 25, 2022: A source says Sylvester Stallone and Jennifer Flavin had "a lot of issues" for years

The day after the news of their split broke, an insider told PEOPLE that the couple had "been unhappy for quite some time." The source said Flavin's decision to file wasn't about "just one issue," adding that the couple "had lots of issues for years and she just had enough."

The source also gave an update on how Flavin was doing post-breakup. "Jen is doing okay," the source shared. "A divorce is never an easy choice and not fun to deal with, but she feels it's for the best."

September 19, 2022: Sylvester Stallone posts photo of himself and Jennifer Flavin amid divorce

Stallone fueled reconciliation rumors when he posted a photo on Instagram of himself and Flavin holding hands. Both Stallone and Flavin have their backs to the camera, making it unclear when the photo was taken.

"Wonderful..." he captioned the post, which also included an old family photo from when his three daughters were little.

September 22, 2022: Sylvester Stallone and Jennifer Flavin do not have a prenup in place

Court documents obtained by TMZ show that Stallone and Flavin did not have a prenup in place when they married in May 1997.

However, the exes have reportedly resolved any major issues and feel confident that they can come to a divorce settlement outside of court.

"The Parties agree that is in the best interests of each of them individually, and more importantly collectively as a family, to resolve all issues attendant to the dissolution of their marriage in a dignified, amicable, and private manner out-of-court," reads the order of abatement, obtained by PEOPLE.

September 23, 2022: Sylvester Stallone and Jennifer Flavin reconcile one month after she filed for divorce

PEOPLE confirmed that Stallone and Flavin are calling off their divorce and are officially back together.

"They've decided to let it ride again. They just decided to reverse course and try again," a source told PEOPLE of their decision.

A rep for Stallone also told Page Six that the pair "decided to meet back up at home, where they talked and were able to work out their differences. They are both extremely happy."

September 26, 2022: A source says Sylvester Stallone and Jennifer Flavin are "slowly figuring things out"

After reconciling with Stallone, Flavin is "much happier," a source close to the former model told PEOPLE. "She has been spending time with Sly and they are slowly figuring things out. Communication has been an issue in the past, but they are both working on communicating better."

"They are amazing together when they are happy," the source added. "Their friends can't imagine them getting a divorce. It really seems they will be able to work things out though. Everyone is happy that they are giving their marriage a second chance."

The insider also explained that the filing came as a surprise to Stallone. "When Jen filed for divorce, she felt she had no option. She felt unheard and was very frustrated," they said. "She had been telling Sly that she was going to file, but it seemed he didn't believe her. It pretty much came as a shock to him. He never wanted a divorce. He always wanted to work things out."

"He has been working hard to win her back. They love each other," the source added. "They want to keep their family together."

Later that week, an insider told PEOPLE that the couple have "a better channel of communication," adding that it's not all "bliss" between the two. "They have their differences, but in a longterm marriage like theirs, ending it and dividing up their assets would be difficult," the source said.

October 6, 2022: Sylvester Stallone and Jennifer Flavin step out in New York City

Stallone and Flavin were photographed walking arm-in-arm in N.Y.C. They strolled the streets in downtown Manhattan before meeting with Leonardo DiCaprio and his father at an art gallery.

The couple also stepped out for a date night that evening at the Polo Bar. The spouses were notably both wearing their wedding rings.

October 17, 2022: A source says Jennifer Flavin "feels heard and appreciated" after calling off divorce

One month after reconciling, a source told PEOPLE that Stallone and Flavin are "working hard to make their marriage work."

"They really don't want a divorce. They both agree that they have issues. There is no blame," the source continued. "Everything is being dealt with in a very mature way and it seems to work. Jen is very happy. Sly is the love of her life. She was just frustrated and needed changes. She is getting those changes now. She loves that Sly is making an effort. She feels heard and appreciated."

October 30, 2022: Sylvester Stallone opens up about nearly getting divorced from Jennifer Flavin

Stallone spoke with the Sunday Times about his marriage to Flavin and their brief split. "Let's just say that it was a very tumultuous time," Stallone said. "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."

November 7, 2022: Sylvester Stallone says divorce drama with Jennifer Flavin will play out on upcoming reality TV series

The Stallone family has signed up for reality TV — and they aren't holding anything back from viewers. The actor revealed to The Hollywood Reporter that his divorce drama and reconciliation with Flavin will be included in the show.

"Of course it's part of the show," Stallone said. "It's the John Lennon thing: 'Life is what happens when you're making other plans.' Hopefully, you're involved with people who understand the foibles of life and the fragility of it and how rare a real good relationship is."

He added: "Sometimes I put the work ahead of [my family], and that is a tragic mistake which won't happen again."

May 11, 2023: Sylvester Stallone and Jennifer Flavin attend the premiere of The Family Stallone

The couple celebrated their new reality series, The Family Stallone, at Torrisi — an Italian restaurant in New York City. The Tulsa King star and Flavin, who were all smiles on the red carpet, wore coordinating black ensembles.

July 6, 2023: Jennifer Flavin celebrates Sylvester Stallone's 77th birthday

In honor of her husband's birthday, Flavin gave Stallone a sweet shout-out on Instagram.

"Happy Birthday my love!!! You bring so much happiness, laughter and love to our beautiful family!!" she captioned a carousel of images.

February 21, 2024: The Family Stallone returns for season 2

The Family Stallone's second season premiered in February 2024, showing Stallone informing his daughters that he and Flavin would be moving to Florida from California now that they had become empty nesters.

“I raised all three of our daughters in California. Everything’s a memory to me, memories of them not being there anymore,” Flavin said in a confessional. “So I needed a big change, and Sly went along with it.”

Though Stallone was originally against the move, he admitted that it was something he wanted to do for his wife.

“No matter how I’m feeling, I owe it to Jen to go through this move," he said.