Ryan and Kelly make amends in "Weight Loss", and Ryan indicates a renewed interest in her. He witnesses Kelly and Darryl kiss, as Kelly looks up to make sure Ryan sees it. In "Business Trip", Ryan and Kelly get back together when he moves back to the annex, though Ryan is uncomfortable again as he only made her breakup with Darryl with the expectation he would react violently, which he did not. In "Frame Toby", Ryan breaks up with her again and leaves the office altogether. Upon his return, the two do not rekindle their relationship, however, they constantly flirt and bicker with each other on Twitter.