Ryan started out as a temp worker. He was initially one of the few - if not only - sane people in the whole office. He stated that in one episode he enjoys not making much of an impact on the goings on in the office because it means that he isn't one of them. After a fire breaks out, Dwight traces it back to Ryan who had accidentally left the toaster oven on too long and he spent the next two years being teased about it.
After mysteriously getting promoted to a corporate position despite his incredibly limited skill set, Ryan became a corrupt yuppie and tries establishing a social networking site. It encounters numerous problems, which he urges the other workers to either fix or cover up in order to save face. Eventually, the police find out and Ryan loses his corporate position. He's sentenced to community work, which prompts Michael to hire him again as a temp. After his rapid rise and fall, Ryan has cracked and now become one of the office weirdos - the very thing he was trying to avoid.
Ryan spends the rest of the series acting like a pretentious hipster who spends more time looking edgy than actually doing any work. He regularly comes up with get-rich-quick schemes, though these never go very far. When Jim Halpert briefly became manager, he noticed how lazy Ryan was and had his desk moved into a cupboard, which Ryan has apparently grown accustomed to as he never leaves even when Jim steps down as manager.
In the final episode, Ryan is revealed to be looking after a baby that an ex-girlfriend dumped on him. He quickly gets rid of the baby at Dwight and Angela's wedding.
Kelly KapoorEditKelly notices Ryan sometime in the second season. Ryan admits he finds Kelly hot and the two start dating. Unfortunately, neither party wants the same thing in their relationship; Ryan wants a casual fling, Kelly wants a long-term relationship with children. Eventually, Ryan gets tired of Kelly and tries looking for excuses to break up with her. When Ryan gets the corporate job, he gleefully dumps Kelly. After losing his position, Ryan tries getting back with Kelly, but is even less enthusiastic about the relationship. The two spend most of their time in a relationship-by-default until Kelly meets Ravi and leaves. Ryan decides he likes the attention he gets from Kelly and goes after her, fully aware that he'll probably wind up dumping her again.
Ryan and Kelly see each other at Dwight and Angela's wedding. Ryan is now a father to a baby boy named Drake. Kelly is still with Ravi, but runs away with Ryan into the sunset, abandoning Ravi and Ryan's son. Ironically, Ryan says "I think I've finally mastered commitment!"
Michael develops a complex man-crush on Ryan early on in Season 2. Ryan is extremely uncomfortable with this, yet exploits it from time to time as it gets him ahead at work despite being underqualified. Michael eventually comes to terms with the fact that Ryan is self-centered and stops treating him like the golden child.
Ryan has a habit of developing an attraction to whomever Jim Halpert is dating. When he found out that Jim and Katy were drifting apart, he casually asks Jim if he can have her number. When Jim was dating Karen, Ryan sheepishly admits to asking her out via email without realising they were together. Finally, when Jim and Pam got together, Ryan tried asking Pam out, only for Pam to tell Ryan she was with Jim now. The irony clearly wasn't lost on Ryan as he exclaimed "you're kidding" before walking out in defeat.
When Ryan dumped Kelly, she started dating Darryl, the warehouse manager. The hyperactive Kelly found Darryl too complex for her tastes and only acted like a girlfriend when Ryan could see them. As Darryl put it "its gotten to the point where I get excited everytime I see that little dude". When Ryan comes back, Kelly starts cheating on Darryl with him. Ryan demands that Kelly dump Darryl if she wants to get serious with Ryan. She does so with a text, to which Darryl acts completely nonplussed. Ryan is disturbed at how easily Darryl let go of Kelly after this, making him regret his decision almost instantly.
Ravi is a pediatrician and Kelly's fiancee in Season 8. Pam set the two up in the hopes that Kelly would get herself out of her dead-end relationship with Ryan and finally settle down with someone who treats her right. When Ryan finds out, he appears in the parking lot riding a horse in traditional Indian garb in the hopes of appealing to Kelly. Kelly makes the mature decision and leaves Ryan, moving to Ohio where they would eventually get married.
Kelly eventually dumps Ravi for Ryan in her typically childish manner. Ravi's annoyed reaction seemed to imply that he wasn't too surprised she would do this.