Winterbourne's name implies that he's quickly headed into old age, even though he's only twenty-seven. And let's face it—his cold, calm demeanor contrasts with Daisy's bubbly warmth. It's no coincidence that flowers die when exposed to frosty winters. Ouch.
He's a nice guy and all, but he's not exactly someone you'd hire to be the spokesman for your new energy drink. Every time he's about to do something, he launches into a series of equivocations. (Should I? Shouldn't I? What will people think?)
When he first sees Daisy, he introduces himself, which doesn't seem to faze her at all, but then we get this: "He wondered whether he had gone too far, but he decided that he must advance farther, rather than retreat. While he was thinking of something else to say, the young lady turned to the little boy again" (1.27). You always kind of want to shove him out of his lazy, hazy indecisive insecurity.
In the beginning, we learn he is involved with an older woman who lives in Geneva, but the circumstances and details of their relationship always remain a mystery: "Very few Americans—indeed, I think none—had ever seen this lady, about whom there were some singular stories" (1.2), a.k.a this love affair with Winterbourne ain't her first rodeo. So, while he's all judgy on Daisy for having some private chats with Giovanelli, he and his older lover haven't exactly been true to their promise rings.
When he's not hot and heavy in Geneva with Ms. X, he's sipping tea with old, uptight ladies like his Aunt, Mrs. Costello, and his friend, Mrs. Walker. Clearly part of his old-fogey-ness is the company he keeps. He's a little arrogant about his education and his knowledge of the world, always assuming he knows more than everyone else.
Winterbourne considers himself a connoisseur of practically everything, even women. After eyeing Daisy's face, he "mentally accused it—very forgivingly—of a want of finish" (1.44). We don't even know what that means—she's not a wood carving, after all—but we find it way harsh.
While he's often busy judging and pontificating, one thing this guy can't do is dance. You know what they say about guys who don't like dancing: don't bring them out dancing or they'll do that thing where they bob their heads back and forth off-rhythm without moving their feet.
Well, that's not exactly what Daisy says. She says, "Of course you don't dance; you're too stiff" (2.149). His stiffness is also the reason she gives for why she'd rather flirt with Giovanelli than with him. Indeed, the chronicle of Winterbourne's stiffness is as vast and interesting as that of Daisy's prettiness. (Check out Daisy's "Character Analysis" to see what we mean.)
On one occasion, Daisy tells him, "I noticed you were as stiff as an umbrella the first time I saw you" (2.220), and on another he reveals, "when I am angry I'm stiffer than ever" (2.160). This has a double meaning. The first: he can't relax. The second: well, we'll just say he's quite fond of Daisy.
So why does this guy like Daisy so much? Well, she's excited about life and all it has to offer. He wants to cut loose but he still really believes in the old conventions of propriety, honor, and decorum. If this were an 80s movie, someone would have to rip the sleeves off his button-down and mess his hair up with some mousse. But this isn't an 80s movie, and though Daisy tries to shake him up a bit, Winterbourne is not that changed by the end of the story.
Want to get deeper in the mind of Winterbourne? Check out our section on "Narrative Technique." After all, we're led into the story mostly through his eyes and opinions.