Season 2: Episode 29: The One With The Five Steaks And An Eggplant
Monica gets promoted and invites the gang to an expensive restaurant to celebrate, causing Rachel, Phoebe and Joey (the "have nots") to really feel the disparity between their incomes and Ross, Monica and Chandler's (the "haves"). Matters get worse when the "have nots" feel the "haves" are extending charity by offering to pay their way so they can all see a Hootie and the Blowfish concert to celebrate Ross' birthday. The whole money issue fades when Monica is unexpectedly fired from her job. Meanwhile, a lonely woman (looking to reunite with a former lover named Bob) gets Chandler's answering machine. Chandler, who was screening calls, picks up and, pretending to be Bob, sets a date with her, planning to be there to pick up the pieces when Bob doesn't show. His evil plan works and he gets a date (which leads to his actually HAVING SEX for the first time in ages), only to have the whole thing backfire when the woman calls Bob (and, of course, gets Chandler who again pretends to be Bob) and confides in him that this new lover (Chandler) wasn't very good.