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The novel begins in New York's Grand Central Station, with Lawrence Selden suddenly "refreshed by the sight" of the beautiful Miss Lily Bart. He wonders what she's doing there and realizes that he's always intrigued by her presence.
Selden deliberately strolls past her to see if she'll say hello or not.
She does. Selden is so arrested by her beauty that he can't believe she's really twenty-nine (which was super-old for a single woman).
Lily explains that she's on her way to Bellomont, the Trenors' house, but missed her train and has two hours to kill. She wants to hang with Selden for a bit.
This amuses Selden, who tends to view things from a slightly aloof and removed vantage point. He agrees to be her escort for the afternoon, while internally musing (for several paragraphs, we might add) on her incredible beauty.
When Lily suggests going someplace "quiet," Selden invites her back to his place, a bachelor pad at an apartment building called the Benedick. He's pleasantly surprised that she accepts his invitation.
(Note: Given the time period we're dealing with here, around 1880, it was definitely risqué for a single woman to be hanging out in a single man's pad without a chaperone. Lily is risking her reputation by doing so, and Selden finds that attractive.)
Lily remarks that Selden's lucky to have his own place like this; too bad she's a woman and isn't allowed to live alone.
Selden notes that their mutual acquaintance Gerty Farish has her own place, but Lily writes her off as an unmarriageable girl who doesn't have to worry about a reputation she doesn't have.
Then, Lily remembers that Gerty is Selden's cousin and apologizes. She's almost envious of Gerty's freedom, since she herself has to live with her aunt, Mrs. Peniston.
Lily banters with Selden, asking why he doesn't come to visit her more often at her aunt's. It can't be that he's afraid she wants to marry him – right?
Selden agrees; he has never once thought that Lily wants to marry him. He is once again amused by her flirtations.
Lily cuts to the chase. She needs a male friend, one who isn't going to try and seduce her into marriage, but who is edgy enough to be honest with her.
Selden gives her a dose of that honesty on the spot: why isn't she married yet at her age? He remarks that marriage is her "vocation," what she was brought up for.
She's waiting for the right man. ("Right" = very, very rich.)
Lily takes a cigarette from Selden and moves around the room, smoking it and examining his book collection of "Americana," a.k.a. American books. He remarks that he's not rich enough to have all the books he wants (which explains why he's not on Lily's list of potential husbands). The books themselves are dull, he says, except to the "real collector" who "values a thing for its rarity." (Go ahead and highlight that line there. Or the second time he says it in the next paragraph. Either one.)
They discuss the very famous Jefferson Gryce collection and other fun facts. Selden's enjoying himself, but he can never spend long with Lily without wondering about her motives.
She questions his financial position further. As it turns out, he's a lawyer, but he doesn't mind having to work for his money.
The two of them briefly discuss the party tonight at the Trenors', and Lily realizes she'd better hurry if she wants to make it on time. They say their good-byes.
As she exits the building, Lily is nervous that someone will see her leaving. She resents the working woman scrubbing the stairs, who forces Lily to ask her to move in order to get by.
As she steps off the stoop, Lily is spotted by Simon Rosedale, a small, blonde, Jewish man with glasses who is new money (he's not from an old family with a history of wealth) and trying to climb the social ladder. Lily explains that she was just visiting her dress-maker at the Benedick.
But Rosedale knows something is up, since the Benedick is a place for bachelors and because, conveniently, he owns the building. But he implicitly assures Lily that her secret is safe with him, and offers to escort her to the train station.
Lily, nervous, refuses his offer and hails a hansom (19th century version of a cab).