The novel opens on the young Tom Ripley walking in a panic through Manhattan. He's running from the police, though it's not entirely clear why, or whether his fear is warranted. He decides to try his luck and duck into a favorite nearby bar for a drink. In the bar, he is approached by a man named Herbert Greenleaf. Greenleaf explains that he is the father of Richard, or Dickie Greenleaf, an old friend of Tom's. Tom barely remembers Dickie, but awkwardly consents to join Mr. Greenleaf for a drink. Mr. Greenleaf, who is under the impression that Tom cares about Dickie a good deal more than he really does, explains that he came to this bar specifically to look for Tom. His son, he says, is living in Europe and refuses to return, even though his mother is sick and his father wants him to take over the family shipbuilding business. Tom offers to write Dickie a letter begging him to come home, and then convinces Mr. Greenleaf to actually send him to Europe to retrieve his son. Tom pretends to be rather reluctant to go, but the trip will help him escape his problems back in New York, so he's actually quite excited by the prospect. Throughout the conversation, he interweaves truth and lies. He avoids correcting Mr. Greenleaf's impression that he is or ever was close with Dickie, and he fabricates a few memories of their friendship for Greenleaf's benefit. He also states that he works as an accountant, though this is not quite true. Regardless, Mr. Greenleaf is both charmed by Tom and so desperate to get his son back that he seems willing to look past any inconsistencies in Tom's story.
The next chapter gives a glimpse into Tom's home life. For the moment he's living with an acquaintance named Bob Delancey. The place is dingy and it embarrasses him, so he never reveals the address. The upside for Tom is that he can use the address to receive mail addressed to George McAlpin. This is how he makes his money, it seems—by posing as McAlpin, pretending to work for the government, and convincing freelancers and artists that they have miscalculated the tax money they owe. He then collects the additional checks they send. Tom is disgusted by his surroundings, but starts to thrill to the idea of the luxurious overseas travel awaiting him. He has been invited to dinner at the Greenleafs' Park Avenue apartment, and considers how he might prepare for the dinner conversation and the journey—perhaps by researching Herbert Greenleaf's business, and by getting a new passport. Before setting off to prepare for his trip, though, Tom sits down and calls a few befuddled taxpayers on the phone, alternately charming and boring them until they agree to send money.
That night, Tom is greeted warmly by Mr. and Mrs. Greenleaf. Their apartment is luxurious, and they have a household staff in charge of cooking and serving dinner. Tom is bored at dinner, and deliberately tests the Greenleafs by creating small inconsistencies in the stories he shares with them. They are clearly not paying close enough attention to catch any of his lies, and in fact, Tom is disappointed when they don't ask him any questions about his (fictional) days studying at Princeton—he once befriended a Princeton student and memorized information about the school for future reference. The Greenleafs mostly want to discuss their son: they show Tom childhood photos of Dickie, which Tom thinks look ridiculous, as well as more recent, and more dignified, ones he's sent from Europe. In the pictures from Europe, he's with an American girl named Marge. Mrs. Greenleaf becomes visibly upset when her absent son is discussed, and she goes to sleep at her husband's urging. Mr. Greenleaf then shares a drink with Tom and tells him that Mrs. Greenleaf, who has leukemia, might not live another year. Though Tom begins the night feeling calm and in control, he starts to panic during his conversation with Mr. Greenleaf. He realizes that this panic began, not when he lied, but when he told a rare truth, explaining to the Greenleafs that his parents died when he was young and that he was raised by his aunt in Boston. This realization doesn't make him feel any better, though. Every time Tom looks in a mirror, he sees dismay on his own face, and he feels as if he can't escape the Greenleafs' apartment quickly enough.
In the days before his trip, New York City itself starts to feel unreal, like a film set. Tom imagines the entire city will disappear when he departs. He's also afraid of the voyage he'll have to make by ocean liner, maybe because his parents drowned in Boston Harbor, leading to a lifelong fear of water. He prepares to move out of his current housing, and has to stop by his previous lodgings in the house of a man named Marc Priminger to pick up some things he's forgotten. Tom hates Marc, whom he sees as a controlling, manipulative man, who offers cheap housing to those who need it as a way to exercise control over them. In fact, Tom was thrown out of Marc's house after a fight over stolen silverware. Tom decides not to tell anyone about his travel plans except for Cleo, a woman he gets along with, though he never does anything traditionally romantic with her. Cleo is eccentric: she paints miniature paintings with a magnifying glass and wears velvet trousers. Tom tells her about his trip over dinner the next night, and enjoys impressing her with his stories about the Greenleafs, and she is in turn thrilled by Tom's news. They get drunk in her family's apartment, fall asleep for a bit, and say goodbye. The next day he goes shopping, on behalf of Mrs. Greenleaf, for some clothes to bring to Dickie. He pays with money from the Greenleafs, but buys a shirt for himself with his own money.
One of the most striking moments in this early section of The Talented Mr. Ripley comes when Tom Ripley leaves Mr. Greenleaf and returns to his own apartment. Though Tom can easily fit in with the wealthy and the powerful, and manipulate them to get what he wants, his own life is one of relative squalor. Moreover, he presents a different version of himself to every person he encounters, sometimes creating even more complications with his lying than is necessary for his safety or comfort. It becomes clear, relatively quickly, that Tom isn't motivated by a mere desire for money or status. Rather, his constant lies seem to be a way of escaping himself. He is constantly bored and convinced that someone is chasing after him, and he tends to react to minor annoyances by feeling completely panicked and crushed. Moreover, as far as anyone can tell in these chapters, Tom could probably use his charm and intelligence to get a stable job and a good place to live. His life of discomfort and inconsistency, in other words, probably doesn't come from necessity so much as it comes from Tom's own neuroticism and inability to maintain relationships.
Even though Tom is clearly not a very nice person, to say the least, his characterization is deepened by a curiously childlike vulnerability. Like a small child, Tom vacillates between feeling exhilarated and devastated. He has little emotional self-control and often worries that he will cry in public. He has little ability to calculate or refrain from risk and yet is constantly afraid—sometimes that he is being followed, sometimes of water. This latter instance of fear seems to be literally linked to his childhood, since Patricia Highsmith lets readers know that Tom's parents drowned when he was a boy. In fact, while we don't yet know much about Tom's past beyond the fact that his parents are dead and he was raised by his aunt, his neuroses are sharpest when he is forced to confront or be reminded of childhood and family. In many ways, Tom's lack of empathy feels like a child's, making him at once frightening and oddly pitiable. For instance, before leaving on his trip, he feels as if New York is unreal and will disappear the moment he departs. This sentiment reveals Tom's general disinterest in the experiences and feelings of others. At the same time, he seems somewhat disturbed by this alien version of the city he inhabits, as if his lack of empathy frightens and inhibits rather than empowers him.
Tom's skill in manipulating others, such as the Greenleafs, seems born less of cool calculation than of neuroticism. When he wants something from someone else, Tom gets it by making them feel bored or frightened, the way that he himself so often feels. For instance, he discourages the Greenleafs from asking too many difficult questions about his education by purposely inventing boring areas of study in order to make them change the subject. When scamming freelancers, Tom cultivates a feeling of immense fear, then carefully describes his false reasoning in such a boring way that people send him money just to escape the emotional storm he has created. In general, Tom is as miserable as he is sinister. His most reliable form of escape from his own misery is through carefully recreating that misery for others, making them feel so upset that they become vulnerable relative to Tom.