#25: The One with the Dress
Throughout the show, Jerry seems to be quite the ladies’ man. He goes on many dates, although none of them ends up in a serious relationship. His most serious relationship throughout the nine seasons of the show is probably the one time he fake-married Courtney Cox. One of the reasons for that seems to be Jerry’s pickiness.

He finds fault in every woman he dates, overlooking his own faults. One time, he dates a woman who wears the same dress every time he sees her. Rather than simply inquiring why she’s always wearing the same item of clothing, Jerry goes a little crazy over this. It is weird, we’ll give him that. He hatches a scheme to get a look at her closet but he never gets an answer – and neither does the audience.