| “ | Darryl Philbin is the most complicated man that I’ve ever met. I mean, who says exactly what they’re thinking? What kind of game is that? | ” | |
—Kelly Kapoor, Money | |||
Kelly starts dating Darryl after Ryan breaks up with her--she flaunts her relationship with Darryl in an attempt to make Ryan jealous.
In the episode "Money," Kelly and Darryl kiss in the conference room in front of Ryan, confirming their relationship. Much like Ryan, Darryl is apathetic about Kelly, but unlike everyone else in the office, he's honest with her. Kelly complains: "Darryl Philbin is the most complicated man that I have ever met. I mean, who says exactly what they're thinking? What kinda game is that?" Darryl seems to catch on that Kelly is only dating him for the purpose to make Ryan jealous. Darryl is frustrated with this.
Their relationship is short-lived; in "Business Trip," Ryan moves back into the annex with Kelly, and although she insists that she will never date him again, they are seen passionately making out. Ryan helps her send a message telling Darryl their relationship is over, and he responds with "It's cool," making Ryan jealous that Darryl wasn't upset over him and Kelly's break-up.
Although Kelly and Darryl split up after Season 5, the two still work at Dunder Mifflin together until Kelly's departure in the beginning of Season 9, when Kelly moves to the University of Miami to be with her new boyfriend. They seem to be civil and friendly after their break-up, although the two of them don't have a signifiant relationship with one another.
Status: Broken Up