Phoebe Cates & Kevin Kline—31 years

At only 19 years old, Phoebe Cates became one of Hollywood’s biggest stars after starring in Fast Times at Ridgemont High. Just a year after this successful film, she met Kevin Kline at an audition for The Big Chill. He was 16 years her senior and already an established actor at the time. It wasn’t until two years after they first met that this couple would even get a chance to go on a date.

To make things happen, Kline even hired Cates’ former assistant and gave her the “mission” of setting up a date between them. The actor really put in the investments to win her over. He even worried that he might “too boring” for his enthusiastic partner. However, it turns out that they had plenty in common! The couple wed in 1989 and welcomed their son, Oliver, in 1991, and their daughter, Greta, in 1994.