Spencer Pratt & Whitney Port

Reality stars Pratt and Port were classmates at Crossroads School, an elite private school in Santa Monica, California. Later, they went on to star in The Hills and The Hills: New Beginnings together.

Pratt revealed in an interview with Entertainment Tonight that “Whitney actually dated my best friend in high school. Her, like, three-year boyfriend was my best friend.” The fact that they were closely associated in high school and then years later ended up starring in The Hills together was a “trip” per Pratt.