From their first encounter in Beverly Hills to the births of their three children, here’s everything to know about Sylvester Stallone and Jennifer Flavin’s relationship timeline. Flavin was a 19-year-old Valley Girl visiting Hollywood with a friend when she and Stallone crossed paths for the first time at a restaurant in Beverly Hills. Stallone, who was in his early 40s at the time, had already been married twice and was a father to two sons, Sage and Seargeoh, with his first wife, Sasha Czack.