#31: Winona Ryder and Richard Gere in Autumn in New York

Richard Gere is another 90s heartthrob who inexplicably starred opposite tons of younger actresses in plenty of rom-coms. Plenty of women find him to be a swoon-worthy silver fox, but some age gaps are just too big not to comment on. There was a 22-year age gap between Richard and his Autumn in New York co-star Winona Ryder. 

The huge age difference is written into the plot of the film, so it doesn’t go unacknowledged. In fact, it’s an integral part of the movie. Richard’s character is an older playboy who loves dating younger, beautiful women and never wants to settle down. Winona plays a whimsical art student half his age who he can’t help but fall in love with. It’s romantic in its own way, I guess.