Sarah Michelle Gellar and Freddie Prinze Jr. – 20 Years
While filming the teen thriller, I Know What You Did Last Summer in 1997, Sarah Michelle Gellar and Freddie Prinze Jr. met, although they didn’t start dating until 2000. They were engaged in April 2001 but didn’t marry until a year later, when they were both in their early twenties in Mexico.

Gellar and Helm married in 1997. They have two children together: a daughter (born in 2009) and a son (born in 2012). During an interview with Us Magazine, Gellar stated that marriage is “work.” “It’s like any other relationship in your life; you must nurture it and devote time to it.”