Sylvester Stallone And Jennifer Flavin Have A Night Out On The Town After Reconciliation Following Split

Sylvester Stallone visiting The Polo Bar
(Image credit: James Devaney/GC Images)

Back in August, it seemed as though Sylvester Stallone and Jennifer Flavin’s 25 years of marriage was coming to an end when Flavin filed for divorce. Six weeks after the bombshell, we learned that the couple had decided to call off their split and stay together. Following the recent relationship news, Stallone and Flavin were spotted enjoying a full day and evening in New York City together. 

On Thursday, the Rocky star and the former model and entrepreneur were seen strolling hand in hand on the streets of downtown Manhattan during the day, before going to an art gallery, reportedly with Leonardo DiCaprio, per People. That evening, Stallone and Flavin got all dressed up for a dinner date at Polo Bar. Check out the pair during their night on the town: 

Sylvester Stallone and Jennifer Flavin leaving The Polo Bar

(Image credit: James Devaney/GC Images)

Just two weeks after it was reported that Sylvester Stallone and his wife were having money negotiations in light of their impending divorce, the couple have done a 180 and look like they’re trying to make things work again. When Flavin filed for divorce on August 19, she accused the actor of moving assets from their marital funds, leading to an “unequal distribution” between them. Stallone denied these claims, saying he “has not engaged” in that behavior. 

When it was revealed that the couple was reconciling after the start of some divorce drama, a report claimed that while they have “their differences,” after 25 years of marriage, ending and dividing up their assets “would be difficult.” The pair reportedly did not have a prenup put in place and initially decided to have their negotiations in private rather than taking it to court. 

Sylvester Stallone and Jennifer Flavin met in 1988  at a restaurant in Beverly Hills, when Flavin was 19 and Stallone was in his early 40s. The couple went public in 1990 during a red carpet appearance at a Los Angeles gala. After having their first child together in 1996, the pair tied the knot in May of 1997 in London. They have three daughters together: Sophia, Sistine and Scarlet Stallone.

Together, the couple have a lot of assets between them at stake should they ever decide to move forward with a divorce. Stallone is a wildly successful actor with multiple film franchises under his belt including Rocky, Rambo and The Expendables movies. The actor is set to soon lead the cast of Tulsa King, which is a Paramount+ series among 2022’s TV schedule, with a premiere this November.  

Flavin on the other hand is the co-owner of the Serious Skin Care company, which is known to sell its products on the Home Shopping Network. 

It looks like things are going well for the couple right now. We’ll continue to keep you posted on the pair’s reconciliation here on CinemaBlend. 

Sarah El-Mahmoud
Staff Writer

Sarah El-Mahmoud has been with CinemaBlend since 2018 after graduating from Cal State Fullerton with a degree in Journalism. In college, she was the Managing Editor of the award-winning college paper, The Daily Titan, where she specialized in writing/editing long-form features, profiles and arts & entertainment coverage, including her first run-in with movie reporting, with a phone interview with Guillermo del Toro for Best Picture winner, The Shape of Water. Now she's into covering YA television and movies, and plenty of horror. Word webslinger. All her writing should be read in Sarah Connor’s Terminator 2 voice over.