50+ Celebrity Relationships With Age Gaps Between Them That Either Made Their Romance Work Or Led To Their Demise

Jennifer Flavin and Sylvester Stallone (With a 22-year age gap)

Sylvester Stallone’s name conjures up images of a sweat-drenched boxer from “Rocky.” The film franchise, perhaps his most famous acting project, also had him working with Jennifer Flavin, who was in “Rocky V.” They initially met in 1988 at a Beverly Hills restaurant.

Stallone and Flavin have a 23-year age difference. In 1994, “The Expendables” star’s bachelor lifestyle drove them to break up. They eventually got back together and went on to tie the knot in 1997. The couple split in August 2022 but were back in each other’s arms by November of that year.

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