Jerry: “Do you date immature men?”
Vanessa: “Almost exclusively.”
The strength of Seinfeld always was about how one relates to society (a theme that would become the ultimate plot point at the end of the series) and the individual’s ability to either maneuver around hurdles or barrel right through them.
“The Stakeout” (which was the third episode produced in the series but aired following the pilot) examines various facets of dating in the late 80s/early 90s which are still pretty timely in the modern age.
As the show opens, Jerry is at a video rental store (remember how popular those were?) with ex-girlfriend Elaine (Julia Louis-Dreyfus in her first appearance on the series) as Elaine tries to come up with a gift for her friend Pamela’s birthday party. Jerry reluctantly agrees to accompany Elaine to the party as long as she’ll attend a family wedding with him. At first, she’s completely against the idea but eventually warms to it when Jerry reminds her that there will “be a lot of people to mock”.
Shortly after they arrive at the party, Jerry becomes enamored of a mystery woman seated across from him and flirts with her while Elaine continuously interrupts their banter. Before the mystery woman leaves, Jerry is only able to obtain snippets of information about her (she’s an attorney and works at Sagman, Bennet, Robbins, Oppenheim and Taft--something he repeats to himself over and over so as not to forget). Elaine is angry with him on the ride home but Jerry knows that he has to find this woman.
When Jerry arrives back at his apartment, his parents, Helen and Morty (only referred to here as "Mom" and "Dad" and played by Liz Sheridan and, in his only appearance as Jerry’s father, Phil Bruns) try to offer advice about relationships but it proves to be slightly out of date and in one case (when Jerry mentions the lack of physical chemistry between him and Elaine) downright awkward. However, his father suggests loitering in the lobby of the building where the law offices are located and search for the mystery woman. Jerry actually likes the idea.
The next scene finds us in the lobby of a busy New York building where Jerry and George wait to see if the woman passes through. Jerry has brought George along to make it seem more natural (because when stalking, it’s always important to have a wingman—otherwise you’re just plain creepy). In the first of what will become an elaborate series of lies as the show progresses as well as a running joke in many future episodes*, George introduces himself as an architect and they tell the woman they’re there to meet Art Vandelay, an importer-exporter. Jerry introduces himself to Vanessa (Lynn Clark) and it’s obvious that they both know their “random” meeting was anything but (leading to the dialogue seen at the beginning of the article).
Of course, Jerry still has to deal with the repercussion of Elaine discovering his ruse which leads to an awkward conversation about the intricacies of navigating a post-breakup/future platonic relationship**. Elaine confesses that she’s never seen Jerry flirt before and he admits to lying about the whole endeavor because he didn’t know how she would react. Elaine ultimately reveals she met a guy by staking him out too.
“The Stakeout” isn’t perfect but, viewed today, it’s still fresher material than some current sitcoms offer. It wisely eschews pop culture references which only enhances its syndication longevity and instead opts for situational humor which can apply to almost any era.
Jerry’s use of George as a “wingman” was way ahead of its time and, with the introduction of certain character eccentricities, “The Stakeout” lays the groundwork for many years to come. This would only be the beginning of shattering barriers to social issues as well as planting seeds for a myriad of recurring stories.
Other silly random observations:
*Contrary to popular belief, Art Vandelay was not George’s first choice for a pseudonym. He originally submitted Bert Harbinson which even Jerry admitted sounded “made up”. George then switches to Art Corr and, after being interrupted by Jerry, adds ”…delay” on the end. It was agreed upon that Art Cordelay would be his fake moniker until he abruptly changes gears when put on the spot as Vanessa approaches them. Art Vandelay was born and would be a recurring gag throughout the series.
**The post-breakup/future platonic relationship would see a brief change in the dynamic nearly a year later in “The Deal”.