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.
Their Initial Hook-Up
After forcing Jim to play matchmaker, Kelly and Ryan hooked up on February 13 in the season 2 episode “Valentine’s Day.” Being a typical guy, Ryan didn’t realize until too late that this was the day before Valentine’s Day, leading to the awkward limbo between casual hook up and relationship. What followed summed up the relationship for most of the series’ run: Ryan wasn’t willing to really commit or break up, while Kelly became the ultimate clingy girlfriend.
Life In The Annex
Kelly and Ryan were as discreet around the office as one would expect, with their drama exacerbated by the fact that they shared a small workspace for a majority of the series. Poor Toby, ever the office whipping boy, was trapped back there with them and forced to bear the brunt of the drama. Whether they were fighting, making out, or being generally inappropriate, Toby had no escape. #SaveToby
The Pregnancy “Scare”
When Ryan gets promoted and leaves to work in the corporate offices, he dumps Kelly in the most unfeeling way. When he returns as her boss, it does not go well. The fake pregnancy scare is the last weapon of women desperate to keep their men, but it pretty much always backfires. Can you imagine these two as parents? I can, and it’s horrible.
After Ryan is fired from his corporate job and returns to the Scranton offices as a temp, Kelly uses her new relationship with Darryl to make Ryan jealous. The two start sneaking around, and of course, Ryan once again commits to more than he is really willing to take on, suggesting that they get back together outright instead of continuing to engage in the affair. Addicted to the cycle, Kelly immediately breaks up with Darryl. The look of regret on Ryan’s face says it all.
When the series finale begins, Kelly is engaged to a hot pediatrician named Ravi and Ryan has a son named Drake (not named after the hip hop artist from 2011). When they are reunited at Dwight and Angela’s wedding, the link between them once again starts to tighten. Inexplicably, Ryan willingly gives his son an allergic reaction just so he can talk to her, but Kelly is probably the only woman in the world who would find that horrible gesture romantic. Despite years of experience telling them that it would never really work, they end up running away together, away from a functional relationship with Ravi and apparently poor baby Drake. It is safe to assume that they probably broke up again in the long run, but maybe they really were meant to be.