Ryan has an on-again, off-again relationship with office chatterbox Kelly Kapoor. The relationship has been troubled from the outset, for Ryan desires a very casual relationship, whereas the overbearing Kelly wants to get married and have children as soon as possible. The two "hooked up" on the eve of Valentine's Day, although Ryan was brusque with her the following day. Things seemed to be starting up between the two again during the office "Casino Night". Ryan and Kelly are later seen dating in "The Convention". Ryan met Kelly's parents during Diwali, but they were not impressed by his low income, desire to travel and saving up money to buy an Xbox, rather than start a family. Ryan has more than once tried unsuccessfully to break up with Kelly, with one of the more notable occurrences after "The Merger" episode.