Fun Bobby was Monica's boyfriend on and off in Season 1 and Season 2. He first appears in "The One With The Monkey", when he shows up as Monica's date to her New Years Party. He does not live up to his nickname, however, when he shows up in a flood of tears and reveals that his grandfather has just died and, not being able to get a flight out, decided to show up at the party. Bobby's drinking problem was most likely a result of his grandfather's death, suffering from depression without alcohol as a result, which would explain why he became so serious.