Warren Beatty and Annette Bening
Warren Beatty, a well-known Hollywood bachelor (or former bachelor, should we say), changed his ways when he met Annette Bening. In 1991, Bening was 33 years old and Beatley was 54 years old when he cast her in his film Bugsy.
Although he promised not to hit on her until the filming was finished, he broke his promise near the end and asked her out to dinner. It didn’t take long for the couple to realize that they were destined to be more than just friends and co-workers, as they married a year later. Furthermore, their 22-year age difference had no effect on their relationship, as they have been together since.