The journey of Sylvester Stallone and Jennifer Flavin: A timeline of their relationship

Sylvester Stallone and Jennifer Flavin have weathered rough patches in their relationship, yet their commitment remains steadfast. In August 2022, after 25 years as a couple, Flavin initiated divorce proceedings against her famous husband. However, just a month later, she decided to call off the divorce.

Their journey began in 1988 at a Beverly Hills restaurant, where Sylvester Stallone and Jennifer Flavin first crossed paths. Their romance experienced ups and downs until they finally tied the knot in 1997. From their wedding in England to the joyous arrivals of their three children, here's the comprehensive timeline of Sylvester Stallone and Jennifer Flavin's relationship.

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1988

Flavin, a 19-year-old was visiting Hollywood with a friend when she and Stallone first met at a restaurant in Beverly Hills. Stallone, then in his early 40s, crossed paths with her during that fateful encounter.

June 1990

In a notable moment of declaration, Sylvester Stallone and Jennifer Flavin showcased their mutual affection for the first time at a prestigious Los Angeles gala in 1990.

March 1994

Stallone terminated their nearly six-year romance by sending Flavin a letter via Federal Express. "He sent me a six-page handwritten letter, in pen," Flavin revealed to People in a 1994 interview, describing the unexpected and somewhat messy conclusion of their relationship.

Flavin only discovered the true reason behind Stallone's decision to end their relationship a few days later. Her agent at the Elite modeling agency revealed to her that Stallone had been involved in an affair with supermodel Janice Dickinson. The revelation sheds light on the circumstances surrounding their breakup, unveiling a painful truth for Flavin. In February, Dickinson gave birth to a baby girl, sparking widespread speculation that the child was Stallone's.

1995

Upon discovering he wasn't the father of Dickinson's baby girl, Stallone sought reconciliation with Flavin, who graciously granted him a second chance in their relationship.

August 1996

Stallone and Flavin celebrated the arrival of their first child together in Miami, FL, joyously welcoming a baby girl named Sophia Rose Stallone into the world.

May 1997

The couple exchanged vows in a civil ceremony at The Dorchester Hotel in London, followed by a chapel ceremony at Blenheim Palace in Oxfordshire. Their intimate wedding was attended by only about a dozen close friends and family members, creating a truly personal and memorable celebration.

June 1998

Stallone and Flavin celebrated the birth of their second child together in Los Angeles, Calif., joyfully welcoming another baby girl named Sistine Rose into their family.

May 2002

Stallone and Flavin joyously welcomed their third child together, another baby girl named Scarlet Rose, into the world in Los Angeles, Calif.

August 2018

Sylvester Stallone and Jennifer Flavin marked Flavin's 50th birthday with a memorable celebration. The couple, accompanied by their three daughters, enjoyed a special outing to Spago restaurant in Beverly Hills, Calif., to honor Flavin's milestone birthday.

May 2022

Sylvester Stallone and Jennifer Flavin commemorated 25 years of marriage with heartfelt tributes to each other on Instagram, marking their enduring love and commitment on this significant milestone.

August 2022

Speculation regarding the status of Stallone and Flavin's marriage surfaced when Stallone was spotted concealing a tattoo of his wife's face with an image of his dog, Butkus, in late August.

September 2022

Just a month after Jennifer Flavin filed for divorce, Sylvester Stallone and she have reconciled. People confirmed that the couple has decided to call off their divorce proceedings and are officially back together.

November 2022

Sylvester Stallone has announced that the divorce drama and subsequent reconciliation with Jennifer Flavin will be featured on their upcoming reality TV series. The Stallone family is set to share their journey with viewers, holding nothing back as they navigate through their personal ups and downs. 

May 2023

Sylvester Stallone and Jennifer Flavin marked the premiere of their new reality series, The Family Stallone, with a special event at Torrisi, an Italian restaurant in New York City. The couple came together to celebrate this exciting moment in their lives amidst the buzz of the premiere.

July 2023

Jennifer Flavin took to Instagram to celebrate Sylvester Stallone's 77th birthday, showering her husband with a heartfelt shout-out to mark the special occasion.

February 2024

The second season of The Family Stallone debuted in February 2024, capturing a pivotal moment as Sylvester Stallone announced to his daughters the family's decision to relocate from California to Florida, now that they had officially become empty nesters.

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