Sarah Michelle Gellar & Freddie Prinze Jr. Were Just Friends Until A Chance Event Changed Everything

Breaking all the rules with straight up wholesomeness.

By Jess Pullar
Of all the iconic Hollywood romances, there are few that span multiple generations. But for both Millennials and Gen-Z, there'll always be Sarah Michelle Gellar and Freddie Prinze Jr.
The pair first started dating at the beginning of the new millennium. It was a time of low-rise jeans and Von Dutch trucker hats. Samantha Mumba reigned supreme and Carrie Bradshaw had only broken up with Aidan for the first time in season three of Sex and the City. Some might say it was a different lifetime, but for Gellar and Prinze, their greatest chapter was only just getting started.
Over the years, the pair have proved that even major celebrities can defeat the Hollywood curse of doomed romances—you only have to look at the pictures for proof.
Below, we look back at Gellar and Prinze's relationship timeline, from co-stars to co-partners in life.
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  • undefined: Jessica Pullar, Jess Pullar