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In his critique of the novella, Richard Hocks suggests that “both Winterbourne and Daisy are in James's language ‘queer mixtures’ of contradictory elements and ‘booked to make a mistake’ with each other because the reactions of each to the other are culturally and socially predetermined” (12). In order to understand Winterbourne’s relation with Daisy it is essential to first consider Winterbourne as an American youth who has been absorbed in to European society following an extended stint in Switzerland to pursue his education.
From the beginning of the narrative, we are led to understand that Winterbourne is a man who values his friendships, who is liked by one and all, with almost no enemies and rumored to be attached to a foreign woman who was said to be older than him. And much of his inhibitions and reservations as well as his inherent reluctance to let off his guard are characteristic of his acquired European lifestyle. And although he considers Daisy to be ‘uncultivated’, Winterbourne takes an almost immediate interest in the young Daisy Miller from the time he meets her on account of her younger sibling Randolph at Vevey in Switzerland, up until her untimely death in Italy.
It is also interesting to note that, although Winterbourne doesn’t share the same joie de vivre and flirtatious demeanor characteristic of Daisy, he does go out of his way to defend her naivete in many instances during the first half of the story. Even when his aunt, Mrs. Costello disapproves of her wandering ways and courtship with men she barely knows, Winterbourne attributes it to her innocence and her love for capturing attention. Winterbourne is instantly charmed by the beautiful American girl’s outspokenness and spontaneity right from their first encounter.
At this juncture, we also get a glimpse in to the titular character’s eye for detail and penchant for appreciating feminine beauty. And although he is confused about her relation with him, Winterbourne still feels an irrepressible attraction towards the young woman’s beauty and charm, something which he believes he has not experienced before. This makes him rather obsessive, and he contemplates how he can bring her in to his dominion and keep her solely to himself. There are quite a few instances exemplifying Winterbourne’s penchant for her beauty and also his obsessive streak.
They were wonderfully pretty eyes; and, indeed, Winterbourne had not seen for a long time anything prettier than his fair countrywoman's various features--her complexion, her nose, her ears, her teeth. He had a great relish for feminine beauty; he was addicted to observing and analyzing it; and as regards this young lady's face he made several observations. (James Part I, 4) And when he sees her later on in Italy, “it seemed to him also that Daisy had never looked so pretty, but this had been an observation of his whenever he met her” (James PartII, 16).
Winterbourne’s subsequent displeasure at her ostentatiously flirtatious nature is evident when he remarks, "You're a very nice girl; but I wish you would flirt with me and me only" (James part2, 11). After Daisy left Vevey, he heard of her presence in Italy surrounded by young Italian men who pleased her a great deal and whose company she thoroughly enjoyed. This was quite contrary to what Winterbourne had hoped she would be, by which he becomes visibly upset. The news that Daisy Miller was surrounded by half a dozen wonderful mustaches
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