Every romantic relationship on the U.S. version of The Office went through a series of ups and downs over the course of the show’s run, but none were as utterly dysfunctional as the one between Ryan Howard and Kelly Kapoor. Played by real best friends/exes/maybe soulmates Mindy Kaling and B.J. Novak, Ryan and Kelly were toxic, but also kind of perfect for each other. Sure, they broke up constantly and drove each other and everyone around them crazy, but deep down, you know that they never would have been able to make it work with anyone else either. Their relationship was a whirlwind of narcissism, lies, and a profound lack of self-awareness, but viewers still wanted to see those crazy kids stick together. The path of love never runs smoothly, which in this case means that the awkwardness was unbearable at times. Let’s take a look at some of the cringeworthy moments from Dunder-Mifflin’s most ridiculous couple.