in the long run, her behavior is more realistic and true to the heart than that of Winterbourne.

Biased by a partiality towards puritanism, Winterbourne demonstrates to be a man who follows the mandates of society, just as they are without question.

Winterbourne had an old attachment for the little metropolis of Calvinism; he had been put to school there as a boy, and he had afterward gone to college there

That places him in a position of a follower, more than a leading man. Although he feels an attraction that sometimes leads him to try and understand Daisy, he is still unable to do so. This is because, far from analyzing her, his style is more to labeland categorize Daisy (and every other woman) within a pre-conceived notion of who is who.

But this young girl was not a coquette in that sense; she was very unsophisticated; she was only a pretty American flirt. Winterbourne was almost grateful for having found the formula that applied to Miss Daisy Miller.

Like his name implies, Winterbourne is a cold and emotionally isolated man. This means that he prefers the propriety of following the rules of decorum to attending to the needs and wants of his life. In his behavior toward Daisy he seems condescending and appears to believe proud, conceited, and sure of his complete superiority of intellect and morals. Yet, although Daisy is not a completely likable character to some, it is fair to state that Winterbourne never gives Daisy a "chance" by trying to view her from a new and perhaps alternative point of view.

Throughout Henry Miller's novel, Winterbourne's opinion of Daisy vacillates between approval and disapproval. Sadly, it is only after her death that he appreciates her and even recognizes he had loved her. Because of the gendered double-standard of the time, Winterbourne has much more freedom than Daisy. He is far less likely to suffer any damage to his reputation for behaving the same as or far worse than Daisy does. There is a big part of the young man that admires her for being spirited and independent. As the quotation reveals, he finds in her an "extraordinary mixture of innocence and crudity."

He enjoys her energy and vitality, which reminds him of the United States and offers a welcome contrast to the narrowly conventional behavior of most of the American expatriates with whom he socializes. His half-hearted wishes to reject the hypocrisy of judgmental people like Mrs. Walker make him appreciate Daisy. But he is also dependent on staying within that social network, so hanging out with Daisy, as she flouts convention and becomes an outsider, is not a viable option.

If he were despicable, he would just seduce her, reasoning that it wouldn't do much more harm to a reputation that was basically shot. Instead, he tries in vain to get her to leave the Coliseum.

Appropriately named, the cold and calculating character of Winterbourne is the epitome of what, in the 21st century, we would call a kind of "hipster".  He has designed his life to play the part of the dandy, the society man, and the connoisseur of everything. While Winterbourne is quite a heavy character to digest, personality wise, it is through his dynamics with Daisy Miller that we realize the extent to which this man is willing to give up his happiness for the sake of keeping up with his social masks. 

In reality, Winterbourne is quite fond of Daisy. Deep inside, the reader can tell that he must have been somewhat jealous of the fact that this girl gets to experience life to the fullest, without any fears of being called out by her peers.

Miss Daisy Miller looked extremely innocent. Some people had told [Winterboure] that, after all, American girls were exceedingly innocent; and others had told him that, after all, they were not. He was inclined to think Miss Daisy Miller was a flirt—a pretty American flirt. He had never, as yet, had any relations with young ladies of this category.

He is curious about this American girl. He is also definitely attracted, to a point, and for someone who lives to look "cool", Winterbourne would have caused a sensation with a young American gal.

Still, while he wants to join in the fun, he cannot get over the social mantras that he grew up with, and which are expected of him to fulfill. It is, in the end, easier for him to suppress his emotions and revert back to the annoying person that he is, than risk his reputation, nay, his status, for the sake of carrying on with someone who is, by all accounts, a naive "nouveau riche". 

Hence, his efforts to understand Daisy denote that there is an interest on his part of getting to know this girl at a deeper level. He does appreciate her joie de vivre, and he may look condescending in his treatment of her, but he is a product of his society: All that he can do is look from the outside in, and wonder about this interesting and strange creature named Daisy.