Jennifer Love Hewitt & Jamie Kennedy
One of the most '90s couples who ever found each other, especially when you consider that they both starred in popular horror movies that were released within a year of each other.
Sean "Diddy" Combs & Jennifer Lopez
Bring back the days when wearing a bandana as a headband was a thing.
Rachel Bilson & Adam Brody
While we love that Seth Cohen and Blair Waldorf just got married, we can't help but long for the time when Seth and Summer were still real-life lovers.
Susan Sarandon & Tim Robbins
These two were a Hollywood anomaly! They were together for over 20 years, so this split was heartbreaking. But a tip of the hat to them for lasting much, much longer than most couples in the business.
Courteney Cox & David Arquette
They were an odd couple, but they worked! Until they didn't. And now we're sad.
Ian Somerhalder & Nina Dobrev
Remember when they were "concerned parents" when their cat got sick? Too cute.