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1
How does the film characterize Baxter?
When we first meet Baxter he is an affable Everyman. He lives a relatively simple life as a corporate underling, his desk one among many in a sea of desks just like it. As it is soon revealed, however, he is helping keep some rather sordid office secrets by lending out his apartment to higher-ups in his office for extramarital affairs. He stays late at the office and kills time so that executives can entertain their mistresses in Manhattan, with the understanding that the executives will help him ascend the corporate ladder more quickly in return for his generosity. Thus, Baxter is a fundamentally passive person, someone to whom things happen. Throughout the film we see him struggle to say "no" to people and assert his autonomy, until the end, when he hands Sheldrake the key to the executive washroom, quits his job, and declares that he's going to "be a mensch."
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2
In what ways is the movie cynical?
While the movie is a romance and has many comedic elements, it is at its core a cynical film. By the end of the film, Baxter has broken out of his position as an assistant executive in order to stand up for what he believes in, and Fran has run away from Sheldrake in an effort to assert her self respect after he has mistreated her. These are hopeful conclusions for these characters in terms of their own consciences, but it lands them both in precarious spots. Meanwhile, the antagonist, Sheldrake, remains almost clinically detached about the damage he has done, and his position as a high-powered executive remains intact. The final image of the film, that of Fran and Baxter playing cards on New Years' Eve in his apartment, is a romantic one, but is also bittersweet, as the viewer knows that the next step is unknown and not entirely sturdy.
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3
What is the symbolic significance of the $100 bill?
The $100 bill that Sheldrake gives Fran on Christmas Eve is symbolically significant because it represents Sheldrake's indifference to her. While she is still holding out hope that he will leave his wife and be with her, she has just found out that he has had a number of affairs with women in the office. The $100 bill is the last straw, symbolizing the fact that he sees their relationship as little more than a transaction. It turns her into a kind of sex worker, rather than "wife material."
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4
How does director Billy Wilder highlight the alienation of office life?
In the very first line of the film, Baxter lists the population of New York City, before listing a number of other statistics and finally listing the specifics of his work day. The "zooming in" of this monologue has the effect of showing how small Baxter is—and indeed, how small we all are—in the grand scheme of things. When we see Baxter at his job at the beginning, he is at the center of a giant room filled with desks exactly like his, with people typing on typewriters exactly like his. This imagery shows us that Baxter is a cog in a giant corporate machine, and his only hope of liberation from it is to either quit or ascend its ranks.
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5
Why does Fran leave Sheldrake on New Years' Eve?
While Fran seems pretty nonplused about being with Sheldrake from the start of their New Years' evening, it is not until she hears that Baxter quit and stood up on her behalf that Fran musters the courage to leave Sheldrake once and for all. Sheldrake tells her that Baxter quit over the fact that he didn't want to lend out his apartment for his affair with Fran. Hearing this, Fran realizes that Baxter really cares about her and doesn't want to see her get hurt by Sheldrake. Baxter's assertion of himself (on her behalf, no less) shows her that she can assert herself too.