Nicole Richie & Brody Jenner
This short-lived romance began and ended in 2006, lasting only about a month and half. Though short-lived, it turns out that the couple wasn’t as shocking as we had initially thought. Richie and Jenner were childhood friends, as the Richie and Jenner families have been longtime family friends. While this former couple might not be that random, it is still a #TBT we didn’t see coming.