SYLVESTER STALLONE AND JENNIFER FLAVIN – 33 YEARS

Sylvester Stallone and Jennifer Flavin share a 22-year marriage with each other. Although their marriage is a happy and long-lasting one, their love story wasn’t always picture-perfect. They met in 1988 when Sylvester, who was 42 years old at the time, just got out of his second marriage. Jennifer was 19, and the pair started dating in a Beverly Hills restaurant. Sylvester, who was feeling a bit down from another failed marriage, gave Jennifer full credit for being the reason why he was loving life again.

Jennifer and Sylvester continued to date for five years until he broke up with her. They eventually got back together, and you could say it was happy ever after as they got married in 1997. Since then, they’ve managed to stay together and have welcomed three beautiful daughters throughout their 24 years of marriage.