Even though the story is told from the point of view of an invisible first person narrator, the perspective belongs to Winterbourne. The reader is made to follow Winterbourne throughout the nouvelle and see the action through his eyes. At times he becomes an unreliable source of information, because of his involvement with and his opinions of Daisy; he lies to Daisy near the end of the story, claiming that her mother believes her to be engaged. Throughout the story, his self-interest propels Daisy and the plot to further heights of confusion. His dual background is also confusing; he is both American and European. Born in the United States, he has lived in Switzerland for a long time. As a result, he follows European custom but gives it an Americanized interpretation.

His name carries definite significance: "winter," as in cold and stiff and "bourne," as in tolerated. He is to some extent a cold-hearted observer, remaining at a distance and never quite putting himself on the line. Daisy increasingly refers to him as "stiff," and in his evaluations of Daisy, his frustrated amazement, he remains frozen, barely able to act. Although he is Daisy's only advocate, he fails to really help her in any way. It is obvious that he is jealous of Giovanelli, but he stays away at a distance, doing nothing about it. In truth, Winterbourne is the perfect tragic observer; he is engaged, yet distant. As a result, he is able to return to his normal life after the action of the story has passed, more or less unaffected

Although presented as a very conservative member of a stilted social institution, Mrs. Costello turns out to be very insightful. She knows how to read social codes and human nature. She understands Giovanelli's intentions with Daisy. She properly judges the Millers as crass and vulgar. She appropriately worries about her nephew's involvement with Daisy. Her predictions and evaluations turn out to be amazingly on target, down to her last remark concerning Daisy's desire for Winterbourne's affection. In the end, she is the wise matron, at once formidable and ridiculous, but always a lady with whom to reckon

Mrs. Miller is the personification of the pathetic mother who has abdicated parental power over her children. Daisy and Randolph run "wild" in Europe, and she does nothing to curb their excesses. She even encourages her daughter to go alone with Winterbourne to the Chillon Castle. Even at the last of the story, she remains oblivious; her daughter is dying and her chief concern seems to be whether or not Daisy was engaged to Giovanelli. Winterbourne reports that Mrs. Miller is a good nurse during Daisy's illness, but it is too late. Her lack of agency has already produced fatal results. Mrs. Miller knew the danger of "Roman fever", but again and again, she fails to provide her daughter with guidance that she needs to save herself. Since Henry James does not reveal Mrs. Miller's reaction to Daisy's death, it is difficult to assess if her character has changed as a result of the tragedy