The “Rocky” star, 78, met the model, 56, in 1988 but abruptly ended things six years later due to his affair with Janice Dickinson.

Sylvester Stallone has one of the wildest dating tales that’s a part of Hollywood gossip history. He isn’t exactly proud of how he handled the awkward moment, but he’s owning up to his mistakes decades later.

Sylvester Stallone admitted that breaking up with wife Jennifer Flavin through the mail was ‘the most insincere breakup’

Sylvester Stallone's romance with wife Jennifer Flavin Stallone hasn’t always been smooth sailing. On the Tuesday, December 3, episode of FOX Nation’s new series Sean, the Rocky alum, 78, revealed he broke up with his spouse via FedEx before the lovebirds reconciled and married in 1997.

Sylvester Stallone sat down with Sean Hannity on the premiere episode of 'Sean' and spilled all the tea about that infamous 1994 letter

Sylvester Stallone says he was a “coward” for sending a breakup letter via FedEx to his now-wife Jennifer Flavin 30 years ago. The “Rambo” actor, 78, opened up about the awkward decision during an interview with Sean Hannity on Fox Nation Tuesday,

Sylvester Stallone has admitted he was a "coward" for breaking up with Jennifer Flavin with a letter. The 78-year-old actor and filmmaker has confessed he once broke up with his now-wife in a letter he sent via FedEx in 1994 after six years of dating.

Stallone, who paid tribute to his wife in a heartwarming Instagram post last year, admitted he deeply regretted his actions when the couple, who have been married for 27 years, were going through a rocky patch.