The year is 1905 in New York City. It opens in Esther's bedroom, where she's sewing a camisole while a party goes on downstairs. Mrs. Dickson comes upstairs to convince Esther to join the party and dance with Mr. Charles, an eligible bachelor. Esther isn't interested in Mr. Charles and, furthermore, is jealous of Corinna Mae, the recipient of the party, as this party celebrates her engagement. Esther has been in the boardinghouse for 18 years and in those years, she's watched 22 girls get married. Esther desperately wants to be married and resents those girls. Mrs. Dickson encourages Esther to marry a man with an income and assures her that her time will come. As she leaves, she gives Esther a letter from a man named George, but refuses to read the letter out loud. George appears and recites his letter: he's working on the Panama Canal and a coworker told him about Esther. He'd like to begin a correspondence.
Esther visits the boudoir of Mrs. Van Buren, a wealthy white lady, to deliver a new corset that's extremely low-cut. Mrs. Van Buren asked for one like the sex workers wear and she's very self-conscious about how she looks in it, but thinks it's the only way to regain her husband's attention. As Esther adjusts the corset, Mrs. Van Buren tenses at the touch. Mrs. Van Buren laments that she has to go to a ball later this evening, where everyone will ask her when she and her husband are going to have a baby. They've been trying, but in a whisper, Mrs. Van Buren confesses that she's not sure she can have children. Esther assures Mrs. Van Buren that she's too beautiful for her husband to stray, and they discuss if it's socially acceptable for a woman to be single. Mrs. Van Buren admits that if she were brave, she'd leave her husband. Esther says that she's received a letter from a man in Panama, but she can't respond because she's illiterate. Mrs. Van Buren excitedly helps Esther draft a letter and George writes again to Esther. He says that the Panama Canal seems like a crazy dream and while he loves the stories his coworkers tell, he now hears Esther's sewing machine in his head.
Esther visits Mr. Marks's flat to buy fabric. He talks her into buying beautiful Japanese silk and suggests she make it into a smoking jacket for her gentleman. They tease each other, discuss the silk, and Mr. Marks compliments Esther's taste in fabric and her skill at sewing. Esther says that the alternative was being a maid, and in her happiness about the fabric, she grabs Mr. Marks's hand. He pulls away. Esther is shocked and offended, but Mr. Marks says that because he's Jewish, he can only touch women who are his wife or relatives. He admits that he's engaged to a woman in Romania whom he's never met.
Mayme, a black sex worker, sits angrily at her piano and Esther lets herself in. A man just tore Mayme's robe and she spits that she hates the way the men touch her. Esther shows her the corset she brought: it's blue, but it looks just like the one she made for Mrs. Van Buren. As Esther laces Mayme into it, she remarks that Mrs. Van Buren and Mayme each want what the other has. When Esther mentions Mr. Marks, Mayme teases her about having a crush, but Esther brings up George. Mayme is dismissive at first, but kindly tells Esther that it's okay to dream. They play-act that they're fancy ladies in Europe. Mayme says that she's a pianist, and Esther says she owns a beauty shop for black ladies. Esther admits truthfully that she has money saved in her crazy quilt to actually start her beauty shop, but Mayme encourages Esther to abandon this dream. She says that dreams are fun to have, but they’re not real. They discuss George's most recent letter and Mayme writes Esther's reply. George writes back that he's been thinking about New York and the suit he'll wear when he meets Esther.
Back in Esther's bedroom, Mrs. Dickson brings in a letter from George. She opened it and read it already. Mrs. Dickson believes that George will take advantage of Esther, but Esther retorts that she doesn't need approval and isn't going to settle for someone like Mr. Charles: she has means and will open her beauty parlor, man or no man. Mrs. Dickson rips up the letter. George starts a letter to Esther, but the scene moves to Mr. Marks's apartment. He and Esther wrap themselves in beautiful blue and magenta silk, and Esther asks why he always wears black. He explains that it's how he shows devotion to God, and he says that his old suit was his father's and connects him to his ancestors. As he turns to wrap up the silk, Esther touches his collar.
In her boudoir, Mrs. Van Buren wears her new corset of magenta silk. She complains about having to go to the opera, and reveals that when she started her period earlier, her husband spat at her. Mrs. Van Buren expresses interest in seeing "a colored show" as Esther adjusts her breasts in the corset. She asks Esther to take her but giggles when Esther asks if she could go to the opera in return. Esther admits that she's afraid that George is falling in love with her, and the women admit secret things that they've done: Mrs. Van Buren has smoked opium, while Esther touched Mr. Marks. In George's next letter, he asks Esther to marry him and confesses his love. Esther tells Mayme about it later. She suggests that this is her only chance to marry and asks Mayme to witness the ceremony, but Mayme refuses. Later, as Mrs. Dickson helps Esther pack, she refuses to let Esther take a frumpy dress and gives her marriage "advice": to attend to George's sexual needs however she must to get him to stay home, and to not let him beat her. She tells Esther that she doesn't need to get married and explains how her own mother forced her to marry up rather than marry for love so she wouldn't have to be a laundress. Her husband was addicted to opium, but she got the boardinghouse out of the deal.
Esther stops in at Mr. Marks's shop and asks for fabric for a wedding dress. She asks for his plainest fabric, which he suggests is for an older woman, and he's embarrassed when he realizes that Esther is the bride. He gifts her his finest wedding fabric and she weeps into it. Mayme, Mrs. Van Buren, Mr. Marks, and Mrs. Dickson appear onstage. Esther and George enter in their wedding attire and as they meet, a camera flashes and a caption reading "Unidentified Negro Couple ca. 1905" appears. George and Esther stand on either side of their bed. George carelessly begins to take off his suit, which Esther carefully folds, and Esther sits with him, shaking. Esther states that she's not beautiful, but she's honest. George removes her dress and touches her, but Esther gets up and offers George a smoking jacket that she made out of Japanese silk. He puts it on, but he's uncomfortable and roughly takes it off. Esther wants to talk before they consummate their marriage and tells him her family history. George isn't interested; his parents were slaves and he doesn't want to tell their stories. Mayme and Mrs. Van Buren appear after Esther and George have sex to help Esther dress.
Several months later, George prepares to go out in a frayed suit, despite Esther's protests that it's Sunday and they've been invited to a church social and Mrs. Dickson's. George is uninterested in going to either and asks for money for a new hat. Esther pulls money out of her crazy quilt for him and asks him to let her mend his shirt before he goes out—people will say bad things about her if he goes out unkempt. Frustrated, George talks about how he can't find work. He gives Esther a letter that a boss gave him and Esther pretends to read it. George finally gives Esther his shirt and lies down. Esther makes a final plea to go to the church social, since she's only been invited to things since they got married. George refuses and says that he feels inadequate since Esther has a job. He mentions that he knows a man who's trying to sell twelve draft horses and asks for the money in Esther's crazy quilt to buy them. Esther refuses, reminding George of her beauty parlor, but George laughs that Esther's looks make her unfit to run a beauty parlor. He tries to tell her that she'd be pretty with lipstick, but she refuses to wear it. George puts on his unfinished shirt and tells Esther where he's going. She says the place is "notorious," and they argue about how unhappy George is in America and in their marriage. Later, Esther goes to Mr. Marks to buy Scottish wool for a suit for George. Mr. Marks tries to sell her lace as well, and Esther insists she can't come anymore.
When Esther visits Mrs. Van Buren next, the white woman is unusually cheerful: her husband went to Europe and will be gone for months. Esther is distracted and sad, which vexes Mrs. Van Buren. Esther admits that George isn't happy and asks Mrs. Van Buren to pay her. Mrs. Van Buren reminisces about writing the letters to George, which makes Esther snap at her. Esther sobs that she lies to George, and Mrs. Van Buren kisses Esther. Esther jerks away as Mrs. Van Buren explains that she loves Esther and that they can still be friends. Angry, Esther says they can't be friends when she can't enter through the front door, even if she's the only person who makes Mrs. Van Buren happy. As Mrs. Van Buren pays Esther, George enters Mayme's bedroom, puts money on her piano, and sits behind her.
Esther visits Mayme, who's thrilled because a man she calls "Songbird" has been coming regularly. He complains about his rich wife. She pulls out the smoking jacket that Esther gave George, which she says that Songbird—George—gave her. Esther tries to convince Mayme to think about the wives of the men she sees, but Mayme is hurt at Esther's lack of support and refuses. Later, Esther pins the pants on George's new suit. He refuses to let her hem them and says he needs to wear them out tonight. In an attempt to keep George at home, Esther puts on lipstick and acts sexy, but George is disgusted. He accuses her of wanting to subjugate him and of not believing in him, since she won't let him buy the draft horses. He kisses her roughly and promises that if he can buy the draft horses, he'll fund her beauty parlor and come home every night. Esther gives George all her money. She admits that she's illiterate, and says that she suspects George is too. George confirms this, and Esther says that they know each other less now than they did when they got married. George promises to bring back horses.
Esther bursts into Mayme's room. She admits that George left her and is cheating on her. She shares that she gave George the money for her beauty parlor and asks if Mayme knows where George is—she's wearing his smoking jacket. Mayme is horrified to learn that Songbird is George, but says that George came in in a new suit last night, threw dice, and used all the money. Mayme hands over the smoking jacket, and Esther forces Mayme to not open the door for George when he knocks. The next day, Esther stops in to see Mr. Marks and gifts him the smoking jacket. He's touched, puts the colorful garment on, and allows Esther to straighten it. Esther returns to Mrs. Dickson's boardinghouse and the older woman agrees to accept Esther back and not ask questions. Esther sits at her sewing machine and the scene turns into a photograph labeled "Unidentified Negro Seamstress, ca. 1905."
