Fun Bobby is first seen in season 1 at Monica and Rachel's New Year's party where Fun Bobby is Monica's date. He however has just lost his Father and has only stopped by before leaving for the funeral. This makes Fun Bobby everything but Fun. In Season two, Fun Bobby is mentioned and is identified as the owner of the clothes on the telephone pole from when he was having sex on the terrace with Monica. Fun Bobby dated Monica again in Season Two until she and the gang realize he is an alcoholic and Monica convinces him to cut back on his drinking. Once she does however, she realizes that there is a reason Fun Bobby is so fun. Once sober, the two split.