Ryan moves back to the annex with Kelly soon before Pam is scheduled to return. He starts showing off in front of Kelly and the two start kissing passionately. Ryan tells Kelly to break up with Darryl via text message. Darryl responds quickly saying "it's cool", with Kelly overjoyed and Ryan shocked. In "Frame Toby", Ryan breaks up with Kelly again, saying he is going with friends to Thailand, but convinces her to have sex with him one last time and give him some traveling money.