The One With The Ball - S5-E21
Factual error: There is no way that a cop and a masseuse could have afforded an apartment in Brooklyn Heights, even in the '90s. (Brooklyn Heights was unaffordable in the '80s.) "Rent control" doesn't explain it either, as a vacant apartment - which is what they are looking for - would be raised to "market rate" if a rent-stabilized tenant moved out. This can't be written off as a character mistake: Gary is not naive or uninformed, and his accent makes clear that he is a New Yorker.
Answer: The statements that she's contradicting (that it is common, it happens to every guy, and it's not a big deal), are the things that a woman commonly says to a man who is suffering from erectile difficulty, typically to assuage his bruised ego. However, most men do not believe that these statements are true, as evidenced by Chandler's outburst. He's so caught up in the proof that women are lying about it that he gives himself away.
Rooster of Doom