Jerry and Elaine have just ended their relationship, but have chosen to remain friends. Elaine invites Jerry to a birthday party; he agrees to go on the condition that she accompanies him to a wedding that he and his parents have been invited to. At the party, Jerry meets an attractive woman named Vanessa. He wants to flirt with her, but is uncomfortable doing so in Elaine's presence. The woman leaves with another man before Jerry finds out her name; however, he learns that she works at a law firm called "Sagman, Bennett, Robbins, Oppenheim and Taff". During the party, Elaine tries to tell Jerry about a dream she had, which featured him. Jerry tries to end the conversation but this results in argument after the party is over.
Back at his apartment, Jerry's parents, Morty and Helen, sleep over, with Jerry sleeping in Kramer's apartment. He talks about the party and claims that he cannot get the phone number of the woman from Elaine because he does not talk about other women with her; additionally, she is still angry with him. Morty suggests that Jerry "stake out" the woman by waiting outside her office, an idea which Jerry likes. The following day, Jerry and George Costanza perform the stake out, pretending that they are coming to see someone else in the building named "Art Corvelay", but under pressure, George insists that they make it "Art Vandelay". They meet the woman, who says the man she left the party with was her cousin. The two then decide to go out on a date.
Later that night, Jerry finds out from his mother that Elaine knows about the stake out. On the day of the wedding, Elaine tells Jerry that the reason that she was angry was because it was the first time she saw him flirt with another woman. They decide that they have to be able to talk more about their relationships if they wish to remain friends. Elaine then reveals that she has recently met a man using a stake out.
This episode features examples of the following:
- Better as Friends: Jerry and Elaine are newly broken-up as this episode begins.
- Characterization Marches On: Jerry's father is a bit craftier here, as opposed to the self-assured yet zanier portrayal of Barney Martin.
- Driving a Desk: The scene where Jerry and Elaine are in a taxi was filmed in a studio using a black background and moving a fake taxi, due to budget restraints, in a method known as "Poor Man's Process."
- Early-Installment Weirdness:
- Apparently Jerry doesn't have a bedroom, as his parents are sleeping on a sleeper sofa.
- Jerry and Elaine's prior romance is a much bigger factor here than it would later become. Justified; they had only just broken up. In later episodes, Jerry has no problem discussing women with her.
- The episode has an unusually happy ending, with Jerry and Elaine solving their relationship issues like mature adults. As they became less and less sympathetic over the course of the show, this rarely happened in subsequent episodes.
- Foreshadowing: Jerry talks with his parents about his and Elaine's recent breakup. His mother scolds him for being too picky about women in relationships and tells him nobody's perfect. It's safe to say that Jerry never takes this advice for the rest of the series.
- Remember the New Guy?: This was Elaine's first episode, but nearly a year passed between the airing of the pilot and this one, and presumably just as much time passed in-universe. She and Jerry met, dated, and broke up in that period, and we see their friendship In Medias Res.
- Scrabble Babble: During a game of Scrabble with Jerry and his mother, the former urges the latter to hurry up and put in a word. Kramer urges her to put "quone" in, which he describes as a medical term. Jerry understandably challenges.
- The Stakeout: As per the title, Jerry and George stake out Vanessa's law firm so Jerry can stage a Meet Cute with her and get a chance to see her again.
- Tuckerization: The names of the people in the title of the law firm are friends Larry David made at college.
