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Jessica is drawn to Helens ad by a Rilke quote and is further delighted by Helens use of the word marinate outside of a cooking context.
Jessica makes her living weaving words together as a journalist (although shes really a frustrated painter) and her biggest romance to date was with her current boss Josh (Scott Cohen, Private Parts), her older brothers college roommate and an aspiring but blocked writer.
But in its best moments, it authentically depicts the awkwardness of new relationships, the confusion of unexpected sexual attraction, and the deep friendships that result from failed romances.Kissing Jessica Stein is flawed, but its sincerity and its willingness to address relationships between non-monosexual women keeps me coming back to it, over and over.Though words like “bisexual” and “queer” are never used, Kissing Jessica Stein is about sexual fluidity.This tension explodes one day, when Jessica is with her mother (whos been setting her up with unsuitable men as far back as she can remember) at the bridal store, trying out a dress for her brothers wedding.Helen passes by, sees Jessica in the dress and asks her what its for.
The Rilke quotation mentioned throughout the film makes this theme obvious: “It is not inertia alone that is responsible for human relationships repeating themselves from case to case, indescribably monotonous and unrenewed: it is shyness before any sort of new, unforeseeable experience with which one does not think oneself able to cope.