Instead of bugging Yunioshi when she forgets her keys, Holly starts bugging the narrator by ringing his apartment at all hours of the night. At first, the narrator thinks that every time the bell rings it's "bad news, a telegram" (3.1), but he soon gets used to Holly saying, "'Sorry darling – I forgot my key'" (3.1). Don't you just love how she calls him "darling" when she's only nineteen?
Even though Holly has no problem bugging the narrator, the two haven't actually talked to each other in person at this point. The narrator sees Holly all the time when he's out walking around the neighborhood, but she doesn't recognize him as the man who lets her into the apartment building at three o'clock in the morning. In fact, "she seem[s] not quite to see [him] at all" when they meet on the street (3.2). Holly, it seems, is wrapped up in her own little world.
We learn a little more about what Holly looks like from the narrator (maybe it's because he's a writer that he notices all these small details about her, or perhaps he finds her attractive). Holly always wears dark glasses, she always looks well put-together, "there [is] a consequential good taste in the plainness of her clothes, the blues and grays that made her, herself, shine so" (3.2). There's something special about Holly that comes not from her clothes or from her dark glasses, but from within the person.
The narrator also remembers seeing Holly at the famous restaurant "21" one night. She's with a bunch of men who remind the narrator of our good friend Mr. Arbuck (remember the guy who fell down the stairs?), and Holly looks utterly bored. He also sees her at a saloon being passed from soldier to soldier as they dance and sing. Clearly, men like Holly very much and pay a lot of attention to her when she's out and about.
The narrator still doesn't meet Holly throughout the summer, but he gets to know her a little better by paying attention to the things she throws away in her wastebasket (this sounds creepier than it really is. Holly's just the kind of girl that people want to know more about. She's kind of illusive and mysterious, and even though the narrator seems like a little bit of a stalker, we think he's really just intrigued by her). He finds "tabloids and travel folders and astrological charts" (3.4), the wrappers from her cigarettes, leftover "cottage cheese and melba toast" (3.4) and hair dye. He also finds loads of "V-letters," which are letters from soldiers overseas (don't forget, World War II is taking place during the story), and many of them profess their love for Holly.
Holly also has a cat, and sometimes when she's letting her hair dry she'll sit on the fire escape with him and play the guitar and sing. She often sings "the show hits" and really likes the songs from Oklahoma!, but she also sings songs that seem to have a little more meaning, "songs that made you wonder where she learned them, where indeed she came from. Harsh-tender wandering tunes with words that smacked of pineywoods or prairie" (3.5). Holly Golightly, it appears, wasn't always a city girl, and although she seems pretty flaky and flighty at times, there is clearly more to her than meets the eye.
Finally, the narrator and Holly come face-to-face one night in September. The narrator has crawled into bed with a drink and a book when he suddenly gets the feeling that someone's watching him. He hears "an abrupt rapping at the window" (3.6) and then spills his drink when he sees a shadow outside. It turns out to be Holly.
When the narrator opens the window, Holly climbs into his room and tells him that she has a horrible man down in her apartment. Apparently he gets pretty mean when he's drinking (Holly shows the narrator a bite mark on her shoulder from her drunk visitor), and Holly climbs out of the bathroom window – not because she's scared of him, but because she's tired of dealing with him. When she sees the narrator looking all "cozy" (3.7) in bed, she can't resist knocking on his window since it's so cold outside.
It seems the narrator reminds Holly of her brother Fred, and that's the other reason she knocks on his window. Holly and her siblings "used to sleep four in a bed, and [Fred] was the only one that ever let [her] hug him on a cold night" (3.7). She asks the narrator if she can call him Fred, which he never really answers, but she starts calling him Fred anyway (so now our narrator has a name, sort of).
As Holly tells the new Fred about her brother Fred, she makes her way farther and farther into the bedroom and declares, "I suppose you think I'm very brazen" (3.7). When the narrator replies, "Not at all" (3.8), Holly "seem[s] disappointed" (3.9). It seems she likes the disapproval she often experiences from others.
Holly comments on the décor in the narrator's apartment by calling it a "chamber of horrors" (3.10), and asks how he can stand living there (she doesn't hold much back, does she?). When the narrator says that a person can "get used to anything" (3.11), Holly's reply to this tells us a lot about her. She declares that a person who allows himself or herself to get used to things "might as well be dead" (3.12), which hints at Holly's chaotic lifestyle. She seems to like change, to like new things and people around her all the time, and to never be in one place long enough to get used to it.
As Holly and the narrator continue talking, she reveals that she "can't get excited by a man until he's forty-two" (3.16). Someone she knows thinks this means that Holly has a "father complex" (3.16), but Holly says that she's "simply trained [herself] to like older men" (3.16).
Talk turns back to her brother Fred, and Holly tells the narrator that she hasn't seen her brother since she left home at fourteen. When he asks her why she left at such a young age, Holly looks at him without answering and rubs her nose. Eventually, the narrator learns that this is Holly's way of saying that "one was trespassing" (3.23) – that a person is getting a little too close for comfort: "Like many people with a bold fondness for volunteering intimate information, anything that suggested a direct question, a pinning-down, put her on guard" (3.23). Holly will share information about herself, but only what she wants to share and only on her terms. When she gets uncomfortable with the narrator's question, she quickly changes the subject and asks him to tell her about one of the stories he's written.
He reads her his most recent story about two women who live together as roommates. One of the women gets engaged, and in order to stop the wedding, the other woman spreads rumors about the first. When the narrator finishes reading, Holly doesn't have the reaction he hopes for. She thinks the story is about lesbians: "'Of course I like dykes themselves. They don't scare me a bit. But stories about dykes bore the bejesus out of me. I just can't put myself in their shoes" (3.29). When the narrator looks confused, Holly asks, "Well really, darling… if it's not about a couple of old bull-dykes, what the hell is it about?" (3.29). Holly isn't very PC here, and she clearly misunderstands what the narrator intended his story to be about, but we kind of have to appreciate her bluntness. She certainly doesn't sugar-coat anything, does she?
Holly, still completely unaware that she's misunderstood his story, asks the narrator if he "happen[s] to know any nice lesbians" (3.31) since she's "looking for a roommate" (3.31). She tells him (again blissfully unconcerned with being PC) that "dykes are wonderful home-makers, they love to do all the work, you never have to bother about brooms and defrosting and sending out the laundry" (3.31). She tells him that she used to live with a lesbian and that people then thought she was gay, too. But she isn't bothered by this, and even tells the narrator that perhaps she is gay: "And of course I am. Everyone is: a bit. So what?" (3.31). So, despite using language that probably makes most of us cringe, Holly seems pretty accepting and open about sexuality.
As the sun comes up, Holly realizes that she's late for a standing appointment at Sing Sing prison (she just gets more and more interesting, doesn't she?). It seems that she gets paid to visit Sally Tomato, a man who's in jail for alleged mafia activities. She tells the narrator, though, that she "adores" (3.43) Sally so much that she would probably go visit him without the money.
We then get the story of how Holly came to be the paid visitor of Sally Tomato. Remember Joe Bell's bar from the first chapter? Well, Sally used to hang out in the back of Joe's bar and he apparently took a liking to Holly. When he's later sent to prison, he has his "lawyer" (Holly's pretty sure he isn't a lawyer at all since they always meet at a hamburger joint) contact Holly and the man offers to pay her one hundred dollars a week to "cheer up a lonely old man" (3.45). Holly assumes that she's being asked to do something unseemly and quickly rejects the offer since she isn't "a nurse that does tricks on the side" (3.45). Plus, she knows she can earn more just by asking her dates for money for the ladies room (who knew going to the ladies room could be such a lucrative business?). But the lawyer tells Holly that Sally has admired her for a long time, so Holly agrees because "it [is] too romantic" (3.45).
This all seems innocent enough, but as we get a little more of the story it seems that Holly's visits serve another purpose besides just keeping old Sally company. The only way she gets paid is to leave messages about the weather for the "lawyer" (we learn here that his name is Mr. O'Shaughnessy). Holly assumes that these messages are just ways for O'Shaughnessy to make sure she's actually been to the prison, but it becomes pretty clear that Sally is passing information to his "lawyer" through Holly. The narrator expresses concern about the arrangement, but Holly blows him off and tells him that she can take care of herself.
Holly eventually makes her way to the bed and asks the narrator if she can lie down next him, just "to rest a moment" (3.55). She tells him to go to sleep, which he pretends to do, and eventually he feels Holly touch his arm very carefully, thinking it won't wake him up. When she starts to whisper something, he first thinks she's talking to him, but it quickly becomes clear that she's pining for her brother Fred: "Poor Fred. [. . .] Where are you, Fred? Because it's cold. There's snow in the wind" (3.56).
At this point, Holly lays her head on the narrator's shoulder and starts to cry (she isn't as carefree as she seems, is she?). When he asks her why she's crying she replies, "I hate snoops" (3.58), and she quickly gets up and heads for the fire escape (it seems he's caught her in a moment of vulnerability and this makes her very, very uncomfortable).