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Content Warning: The source material and guide feature depictions of sexual harassment.
Dorothy “Dot” Clark, a public relations professional in New York City, feels uninspired at work and in her relationship. As she struggles with a pitch for a new healthcare client, she contemplates the flowers sent by her boyfriend of six months, Ryan Montgomery. Though her junior colleagues are impressed by the gesture, she knows her relationship is failing.
Dot reflects on meeting Ryan, a handsome finance worker, on a dating app. Initially, his structured life plan—which includes marriage by age 28—seemed appealing. Knowing that he is 27, she has the sense he is going to propose soon and finds it alarming. Dot has grown bored with Ryan’s narrow interests in money and golf, while his lack of curiosity and disinterest in politics increasingly highlight how little they have in common. She has generally started avoiding seeing him or responding to his messages. His recent “love bombing” with gifts like flowers and chocolates feels less like affection and more like a desperate, and failing, attempt to win her back.
Dot’s thoughts are interrupted by her senior vice president, a boss she dislikes for his condescending attitude and for promoting a less-qualified male colleague over her. After he leaves, Dot finishes her work presentation, feeling a growing sense of career dissatisfaction and a fear that she is falling behind in life. She is hosting her friends, Mary and Harper, for a political conference call later that evening. Before leaving, Dot performs her meticulous clean-desk routine, a source of personal organization. She hesitates, then decides to leave Ryan’s flowers at the office, turning out the light and heading home.
Walking home through Central Park, Dot listens to a political podcast, a habit from her politically active upbringing. At her apartment building, the Buckley, she speaks with her favorite doorman, Albert Hawkins, an elderly veteran she has known since childhood. They briefly discuss the upcoming presidential election. Inside her apartment, Dot receives a text from Ryan inviting her to a special-occasion dinner at Peak, a restaurant on the 101st floor. Suspecting he plans to propose, she grows anxious and puts her phone down without replying.
The narrative shifts to Mary Russo, a young lawyer working in New York City. While successful and well-paid, she finds corporate law unfulfilling and boring. Tasked with delivering a phone charger to a partner at the district court, Mary passes a Legal Aid office. A sign asking for volunteers for Family Court catches her eye. A handsome man named Manny Rios comes out to speak with her, explaining the need for advocates for foster children. They share a flirtatious conversation, and Mary feels an unexpected spark of attraction. She has avoided dating since ending a frightening, possessive relationship with a law-school boyfriend that resulted in a restraining order, which makes this attraction surprise her. She ignores it and quickly continues on her errand.
Harper Lee Adler, an English teacher at a private high school who once dreamed of becoming a novelist, prepares to meet with parents angry about their son’s poor grade. She reflects on how she ended up teaching after following her surfer boyfriend, Charles “Kai” Calhoun, on a volunteer trip to Senegal. The trip ended in heartbreak when she discovered him cheating. She returned to New York, moving back into her childhood bedroom. In the present, the school principal, Edith Thistlewood, fails to support Harper, forcing her to allow the student to rewrite his paper. Upset, Harper leaves school and walks to Dot’s apartment. She meets Mary outside the building, and they go up together.
At Dot’s apartment, the three friends discuss their professional frustrations. Harper recounts her troubles with entitled parents and her lingering anger toward Kai. They join a political Zoom call hosted by a former NYU classmate, Kaitlyn “Kitty” Bell, who is now the executive director of a Democratic super PAC called For the Win (FTW).
After a kick-off from George and Amal Clooney, Kitty outlines FTW’s new initiative: selected volunteers will have their expenses paid to relocate to battleground states for approximately ten and a half months, gathering observations and political intelligence for the organization. Wisconsin is FTW’s top target. Watching Kitty makes Dot reconsider her own decision to pursue tech PR rather than politics. Acting on impulse, she asks a question about the Wisconsin location, surprising Mary and Harper. Although Dot insists she is merely curious, the opportunity clearly appeals to her.
The next morning, Dot thinks about Kitty’s political project during her run. Before work, she finally texts Ryan, suggesting a more casual dinner at Joanne, a restaurant near her apartment, which he agrees to. At the office, Dot discovers a confidential employee review spreadsheet left at the printer. Nearly everyone is rated “Meets” or “Below” expectations, while only Dot and an accounting employee receive “Exceeds.” A note directs the company to reassign client work to Dot. She realizes the firm plans to downsize and load the departing employees’ work onto her even though she already works 12-hour days. The discovery confirms her dissatisfaction with her job and strengthens her desire for a change.
After a successful pitch meeting, Dot deals with a hostile client who threatens to fire the firm if she doesn’t get him booked on CNBC by the end of the day. Feeling overwhelmed by the pressures of her job and personal life, she goes for a walk down Fifth Avenue. Her day takes a shocking turn when she sees Ryan walking into Tiffany & Co. Convinced he is buying an engagement ring, she follows him inside while on a panicked phone call with Mary. Hiding behind a pillar, Dot watches him look at rings on the third floor before she flees the store, her anxieties now at a breaking point.
Mary endures a boring blind date with Ricky Molinaro, a man from her Staten Island neighborhood whom her mother set her up with. The next day, questioning whether corporate law is meaningful enough for her, she returns to the Legal Aid office to inquire about volunteering. She hopes to see Manny again, but her hopes are dashed when he introduces her to his boyfriend, Rafael Hernandez. Mortified by her misinterpretation of their earlier interaction, Mary lies and says she has been called back to work, then hurriedly leaves.
Harper’s day begins with a flood in her apartment bathroom. At school, she learns that another wealthy family has filed an official complaint against her. The headmaster, Phil Swift, appears sympathetic and invites her to dinner to discuss the matter. However, his true intentions become clear at dinner when he talks about fixing her problems then places a hotel key card on the bar. Disgusted and furious, Harper pretends to use the restroom, slips out of the restaurant, and takes a taxi to her brother Ernest’s apartment.
Dot’s dinner with Ryan is tense. He announces he has booked them a weekend trip to a vineyard where a friend recently proposed. The conversation worsens when he praises a Republican governor’s policies supporting stay-at-home mothers, revealing his traditional expectations for a wife. Horrified, Dot realizes their values are completely misaligned.
Outside her building, she refuses to let him come up and ends their relationship on the street. After he leaves, Albert comforts her as she cries. The next morning, Dot wakes up with a new sense of clarity and a career idea.
The three friends meet for dinner. Dot confirms she broke up with Ryan, and Harper announces she quit her teaching job after the headmaster sexually harassed her. With all of them feeling stuck, Dot formally proposes they move to Cedar Falls, Wisconsin, for the year to participate in FTW’s election project. She reiterates that FTW will cover all the expenses.
Mary is initially hesitant to leave New York, and Harper worries about money. However, the prospect of a meaningful adventure, a fresh start, and a chance for Harper to focus on her writing proves convincing. After confirming that they will return the day after the election, November 8, they all agree. Dot immediately calls Kitty to accept the offer.
The following weeks are a flurry of preparations. Dot’s and Harper’s families enthusiastically support the move, with Harper’s parents even giving her money to support her fresh start. Dot resigns from her job and shares an emotional goodbye with Albert, while Mary gets approval to work remotely from her law firm. After Mary sends a threatening legal letter, Harper’s landlord agrees to release her from her lease. Her family is sad to see her go but gives her their blessing. The night before their departure, the friends exchange excited texts. On the plane to Milwaukee, they are filled with anticipation for their adventure. As the plane takes off, Dot looks out at the New York City skyline and promises to come back.
Dot’s meticulous clean-desk routine, a ritual of imposing order on her chaotic professional life, contrasts sharply with her growing fear that she has constructed the wrong future for herself. Although “having everything planned out” has always been her “go-to move,” Dot realizes that “half her plans weren’t panning out and the other half were hemming her in” (5). This sense of discontent is shared by her friends. Despite being on track for a lucrative corporate law career and eventual corner office, Mary questions, “[w]as this really what she wanted to do with her life? Was there more to life than billable hours for bankers?” (15). Meanwhile, Harper’s life is a series of escalating disasters, from a cheating boyfriend to a flooded apartment and an exploitative teaching job. These opening chapters establish New York City as a place of both personal and professional stagnation for the three women. Despite its glamour and opportunity, the city is becomes the center of disappointing relationships and existential anxiety. The setting therefore creates an important contrast between the lives the women have built in New York and the possibility of something different beyond it. Their shared malaise creates the important precondition for their eventual, radical decision to leave, setting up their collective journey as a quest for Finding Authentic Identity Outside the City.
Central to the protagonists’ discontent in the city are their romantic relationships which underscore the hollowness of their current lives. Dot’s decision to end her relationship with Ryan culminates in his expression of admiration for a Republican governor’s policies, revealing a chasm between their core values and expectations for the future. What initially attracted Dot—his orderly, planned-out life—comes to feel like a trap when she realizes his plans for her are incompatible with her own ambitions. Ryan’s determination to marry by 28 once appealed to Dot’s own tendency to plan ahead, but as the possibility of a proposal approaches, she notes how “[h]is clock was ticking. And to dot, it started to sound more like a bomb” (5). Her decision is a rejection of both Ryan and the life he represents: a predictable existence focused on market performance and traditional gender roles. Harper’s romance with Kai ends for similar reasons of mismatched values, when his superficial charm is exposed as faithlessness. Mary’s romantic prospects are a series of dead ends, from a boring blind date arranged by her mother to a mortifying misinterpretation of a flirtation with a man who has a boyfriend. These experiences collectively argue that, for these women, a successful partnership requires something deeper than predetermined expectations or surface-level attraction. Their romantic failures are thus a key catalyst for their larger search for authenticity.
The headmaster Phil Swift’s proposition to Harper exemplifies the toxic power dynamics the women face in their careers. Over dinner, he offers to intervene in a parent complaint, telling her, “I could talk to the Laschers privately. And we can make this all go away,” before adding the suggestive condition, “[i]f you want it to” (49). His subsequent presentation of a hotel key card makes the implied exchange explicit, exposing the moral decay beneath the school’s prestigious facade. In a similar moment of professional exploitation, Dot discovers a confidential spreadsheet revealing her PR firm’s plan to lay off junior staff and shift their workload onto her without a raise, all while she endures abusive clients who demand to know, “Who. Is. The. Boss. Of. You?” before answering his own question: “I am. I am the boss of you” (37). Mary, though not subject to the same overt abuse, feels the quiet suffocation of a corporate law career that offers financial security but no personal meaning. Together, these incidents depict professional environments in which achievement has failed to provide the women with the fulfillment they expected. For Dot and Harper especially, professional success leaves them vulnerable to exploitation by powerful men and institutions, while Mary increasingly questions whether success without meaningful purpose is enough. This disillusionment strips their New York careers of much of their remaining glamour and makes the prospect of leaving increasingly attractive.
At the moment they need it, Kitty provides an important contrast to their dissatisfaction. Watching Kitty lead thousands of people on a political conference call makes Dot question her own choices. She sees Kitty as having “put herself on the fast track” with a “glamorous, meaningful job” that is “everything high-tech PR [is] not” (30). In this way, Kitty functions as a foil to Dot, embodying the politically engaged career path Dot considered but ultimately rejected after college. Her confidence and assuredness presents a coherent story of lifelong political ambition, intensifying Dot’s fear that, unlike Kitty, she has chosen the wrong path.
The women end this section of the text by approaching Cedar Falls as temporary, establishing a firm endpoint for their experiment and intending to return to New York immediately after the election. At the airport, Mary urges the women to embrace the uncertainty of their decision: “It’s an adventure. It won’t be perfect. Let’s just roll with it, okay? We may never get the chance to be spontaneous again,” ultimately calling Wisconsin “our chance for one more roll of the dice before permanent life sets in” (68). Her words capture the significance of their departure. Cedar Falls represents an opportunity to interrupt the trajectories that their careers, relationships, and expectations seem to have established for them and discover what they actually want before those identities become permanent. Dot’s words to the New York skyline as their plane leaves, “[b]e right back” (69), captures her certainty that this decision is only a break. She believes she is temporarily stepping away from her real life rather than beginning a fundamentally different one, giving Part 1 an appropriately ironic conclusion and laying the foundation for the theme of Finding Authentic Identity Outside the City.



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