A Timeline of Sylvester Stallone and Jennifer Flavin's 26-Year Marriage

The couple first crossed paths in 1988 at a West Hollywood restaurant, according to People. Stallone was 42 years old and a two-time divorcé (he was married to Sasha Czack from 1974-1984 and Brigitte Nielsen from 1985-1987). Flavin, meanwhile, was a 19-year-old model from San Fernando Valley, CA.

"I'd come over, and we'd watch a movie, cook dinner, goof around with the dog or walk on the beach," Flavin told People in 1994, describing the early days of their relationship. The pair made their red carpet debut as a couple in 1990.