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?" 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 re