"Fun Bobby" (Robert) (Vincent Ventresca): Monica's alcoholic boyfriend. In his first appearance in "The One with the Monkey", his "fun" is sapped at Monica's New Year's party after his grandfather died, but his depression does not stop Monica, annoyed that he's "bringing her party down" from putting a party horn in his mouth and forcing him to blow on it, to his bemusement. In "The One with Russ", the gang discovers that alcohol puts the "fun" into Fun Bobby. Monica tries to wean him off drinking but regrets it when he becomes extremely boring. Monica then begins drinking on their dates, so that she could sit through his mind-numbingly dull stories. Bobby then breaks up with Monica, stating that he is not strong enough for a co-dependent relationship. It is revealed in the episode "The One with Phoebe's Husband" that the underwear on the telephone pole was Monica's when she was having sex with Fun Bobby on the terrace.