Ryan and Kelly have had a strained relationship, since the two have opposite personalities. They began dating on Valentine's Day Eve 2006, and Ryan tried to break up with Kelly multiple times unsuccessfully. He finally succeeded when he left for a new job in New York. It was rekindled when after being fired from corporate and rehired again as a temp receptionist while Pam was at art school in NY. Kelly had been dating Darryl since, and used their relationship to make Ryan jealous. Once Pam returned from New York, Ryan returned to the annex to share the nook with Kelly. Shortly afterwards, Ryan left Dunder Mifflin and Kelly again ("to go to Thailand"), returning months later to work with Michael at his new paper company. Sometime after Michael and Ryan (along with Pam) rejoined Dunder Miffl