When Tom boards his boat to Europe, he is dismayed almost to the point of tears to find out that his friend Bob (the person he has been living with) and Bob's group of friends are waiting in his cabin to see him off. Tom only likes one of these men, Paul, so he sneaks out for a private chat with him. Paul believes that Tom works for the Associated Press, and Tom pretends to be traveling for work until the ship departs and the uninvited visitors are forced to leave. He discovers a fruit basket from the Greenleafs in his cabin and feels unexpectedly moved to tears. On the ship, Tom tries to cultivate an air of mystery. He buys a cap and revels in the realization that, with a simple disguise, he can make himself look like anyone at all. He turns down an invitation to play bridge with the other passengers, instead rapturously considering how he might alter his life by finding work in Europe and never coming home. He also writes some letters—one to the Greenleafs, though he isn't able to send it because he impulsively adds a lengthy and completely fictional postscript about persuading their son to come home, and one to his aunt Dottie. He tells Dottie not to send him any more checks. Dickie resents his aunt, who cared for him after his parents' deaths, for often sending him very small checks and for mentioning the financial difficulty she dealt with when raising him. Though he has previously relied on her small financial gifts, he now decides that they won't be necessary during his new life in Europe. He remembers an occasion on which his aunt called him a "sissy," saying his father had been the same way, and reflects that her treatment is to blame for his inability to stick to a job or life path.
After docking in Europe, Tom takes the train from Paris to Naples. He catches glimpses of Paris and Pisa through the windows, and is heartened by them. In Naples, he wearily hands over a few coins to an aggressive local boy who clearly wants money in exchange for help reaching his hotel, and then enjoys a dinner on the beach, though his rudimentary Italian means he fails to ask for the food he wants. The next day he takes a bus to Dickie's seaside town, Mongibello. After asking a few locals, he is able to discern that Dickie and his friend Marge are out at the beach. He buys a bathing suit and goes down to say hello. Dickie has no idea who Tom is and doesn't much seem to care, but he and Marge invite Tom to swim with them and then to join them at Dickie's house for lunch. Tom suspects that Dickie's generosity is largely prompted by Marge, but accepts. He feels somewhat alienated beside the two of them, especially since they mostly discuss minutiae of local life. He also concludes that Marge is romantically interested in Dickie, but that Dickie doesn't return the feeling. Dickie, meanwhile, seems rather irritable about Tom's presence, presumably since Tom is a messenger from his parents. He seems unenthusiastic about the prospect of meeting again. Back at his hotel, Tom vomits and falls asleep. When he wakes, he hears Marge and Dickie outside and spies on them from his window while they walk to the sea to go for a sail. He bitterly realizes that Dickie has no reason to return to America, even though he would have a luxurious life there, since his life in Europe is both luxurious and unencumbered by family and work. Tom realizes that he must slowly work to make Dickie like him before trying to convince him farther.
Tom's feelings of despair and alienation during his time with Dickie don't seem to be entirely rooted in a mere desire to fulfill his promise to the Greenleafs. His own sense of self-worth rides heavily on the encounter. He wants Dickie to like him "more than anything else in the world," and he repeatedly tells himself that Dickie and Marge's romance is one-sided. On the one hand, this seems to be evidence that Tom is himself romantically or sexually interested in Dickie. Yet his fascination doesn't seem to stop at straightforward attraction. He's also clearly intrigued by, and envious of, Dickie and Marge's wealth. He closely examines Dickie's rings at lunch, and dwells on both the loveliness of his home and the attentiveness of his maid.
Tom has a tendency to equate wealth with freedom. Even though Dickie's parents want him to come home, his intergenerational wealth frees him to live in Europe, focusing entirely on his own enjoyment and artistic pursuits. When remembering his childhood, Tom rarely distinguishes between truly traumatic memories and more mild annoyances. Thus, he sees his aunt's unkindness as a terrible cruelty, affecting his ability to live a normal life. He sees her actual kindness, such as sending him money, as an affront and a continuation of previous traumas. For Tom, receiving both money and care from relatives is a symbol of his own dependence on others and of his unremarkable, seemingly middle-class background. He wishes to be both remarkable and independent, and therefore envies Dickie, whose wealth gives him the ability to stand out and live according to his whims.
This general inclination to conflate trauma with annoyance and annoyance with well-meaning generosity is one of Tom Ripley's more interesting and disarming characteristics. While he lacks self-awareness, and often experiences sudden mood swings without knowing why, he has a strong impulse to understand himself and his own emotions. He borrows from the toolkit of psychoanalysis, which encourages individuals to understand and change themselves by uncovering painful memories, but he rarely uses his exploration or reminiscing to actually question or change his own behavior. Instead, he turns each potential moment of truth-seeking into an opportunity to feel victimized. And, rather than begin a painful process of bettering himself and changing his life, Tom simply rachets between feelings of despair and triumph. In his triumphant periods, he feels sure that his problems will disappear with relatively little effort. But, because he has no concrete plans or underlying emotional reason to think his life will change, minor inconveniences or irritations ruin his good mood.