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Sylvester Stallone just opened up about one of his biggest relationship regrets involving his wife.
During an interview on the debut episode of Sean with Sean Hannity on Tuesday, December 3, the actor admitted that sending a breakup letter to now-wife Jennifer Flavin via FedEx in 1994 was a cowardly move.
Stallone, 78, reflected on his note to Flavin, 56, calling it “the most insincere breakup you can get.” He added, “You can’t even say… you put it down in words ’cause you don’t have the guts to do it face to face.”
Sylvester Stallone attends amfAR Las Vegas at Wynn Las Vegas on November 22, 2024 in Las Vegas, Nevada. Stallone recently revealed his one relationship regret. Sylvester Stallone attends amfAR Las Vegas at Wynn Las Vegas on November 22, 2024 in Las Vegas, Nevada. Stallone recently revealed his one relationship regret. David Becker/Getty Images
Stallone explained that at the time, he wasn’t equipped to handle relationships in a healthy way due to his difficult upbringing. “I was raised in an incredibly dysfunctional family. No love. No pat. No handshake… I got the s**t beat [out of me],” he revealed in the episode. He admitted that his tough upbringing didn’t help him navigate his personal life, especially in terms of communication and maintaining relationships.
Despite the rough patch, Stallone was able to reconcile with Flavin –– not once, but twice. The couple first met in 1988, but their relationship hit a major hurdle in 1994 after Flavin received the aforementioned six-page handwritten letter ending things.
However, the letter did not mention Stallone’s infidelity with supermodel Janice Dickinson, which Flavin later discovered. After a period of reflection, Flavin ended up giving the Rocky star a second chance, eventually marrying in 1997.
The couple faced another challenge in 2022 when Flavin filed for divorce, only to reconcile a month later. Stallone admitted to The Hollywood Reporter at the time that prioritizing his career over family had almost cost him his marriage. “Sometimes I put the work ahead of [my family], and that is a tragic mistake which won’t happen again,” he stated.
Stallone has five children in total. He has three daughters with Flavin: Sophia, 26, Sistine, 24, and Scarlet, 20. He also has two sons from his previous marriage to Sasha Czack – whom he was married to from 1974 to 1985 – Seargeoh, 44, and Sage, the latter of whom passed away in 2012 at the age of 36.
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