What happens during Dexter's first and second encounters with Judy Jones in "Winter Dreams"?

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Judy is less a person for Dexter than a kind of ideal, a thing or way of being that he desires to attain. It is her stubborn subjectivity, however—the fact of her living her own life, independent of his own wishes—that both confuses and frustrates him but also causes her to be endlessly fascinating.

Dexter first meets Judy when she is eleven (and he 14) at the golf course where he is a caddy. Even though she is younger, she is clearly used to ordering people around, something Dexter finds intriguing and funny. But when he is ordered to be her caddy, he decides to quit his job rather than submit. In doing so, he is asserting his equality with her.

The second time they meet, Dexter, now in his 20s, is on his way to making a fortune in the laundry business and again meets Judy on the golf course. He is transfixed by her beauty and agrees to have dinner with her the next night. At dinner, Judy confides in him that she has just broken up with her boyfriend, because she found out he was poor. Dexter tells her he is rich. They kiss, and Dexter realizes that "he had wanted Judy Jones ever since he was a proud, desirous little boy."

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Judy Jones is only eleven when Dexter speaks to her for the first time. She is headstrong and spirited, threatening to beat her nurse with a golf club as they await a caddy. Dexter finds her beautiful even at eleven and knows that she is "destined after a few years to be inexpressibly lovely and bring no end of misery to a great number of men." Judy Jones lights a "spark" in him, and he finds himself trying to stay out of her line of sight so that he can enjoy her spirited exchanges with the adults around her. And then he quits his job as a caddy and walks away.

When Dexter is twenty-three, an "enormous thing happen[s]." While he is playing golf with some other men, a ball comes flying out of nowhere and hits one of the other men. None other than Judy Jones appears to lay claim to the ball, and later that night, she finds him at the golf club. She asks Dexter to drive her boat so that she can practice surfing behind it, and he agrees. As she swims out to her board, Dexter falls fully under the spell of her beauty:

Watching her was without effort to the eye, watching a branch waving or a sea-gull flying. Her arms, burned to butternut, moved sinuously among the dull platinum ripples, elbow appearing first, casting the forearm back with a cadence of falling water, then reaching out and down, stabbing a path ahead.

Judy then invites him to dinner the next night, establishing the nature of their relationship for years to come: Judy establishes the terms of their encounters, and Dexter follows her desires.

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Dexter Green first meets Judy Jones while working as a caddy at the Sherry Island Golf Club in Minnesota. He is immediately smitten with her. However, Dexter's feelings for Judy go far beyond the typical teenage crush. He becomes obsessed with the idea of making Judy his. Dexter's first meeting with Judy inspires such an intense feeling within him that he decides to quit his job as a caddy the same day of their meeting. Dexter dedicates himself to becoming a member of the upper class, which, in his mind, is what he needs to do to earn Judy's affection.

Driven by his first meeting with Judy, Dexter ultimately decides to leave Minnesota to attend an elite college on the East Coast. He returns to Minnesota after graduating from school. Dexter is now in his early twenties and hoping to start a successful career as a businessman. This sets the stage for Dexter and Judy's second meeting.

Fittingly, the two reunite at the same Sherry Island Golf Club where they first met. To Dexter's delight, the two hit it off over dinner and begin a relationship. However, "Winter Dreams" doesn't end here. Instead, Dexter and Judy's relationship becomes turbulent, and the two ultimately part ways.

In the end, even though Dexter achieves his goal of becoming a member of the upper class, he never quite possesses Judy the way he dreamed about as a teenager.

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Judy Jones has the uncanny ability to affect the whole direction of Dexter's life according to her whims.  The first time they meet, Dexter is fourteen and Judy is eleven.  Dexter, who is working as a caddy at Sherry Island Golf Club for pocket money, dreams of becoming a golf pro and out-playing the wealthy members who frequent his place of employment.  When the beautiful Judy comes to play golf and treats him as an inferior, he abruptly quits his job.

After attending a prestigious college he can not easily afford and borrowing money to go into business, Dexter returns to Sherry Island to play golf as a successful, twenty-three-year-old businessman.  In a twist of fate, Judy is playing there as well, and accidentally hits one of Dexter's party with her ball.  Dexter falls in love with her, and the two begin a tumultuous relationship.

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When does Dexter first encounter Judy Jones in F. Scott Fitzgerald's "Winter Dreams"?

Dexter first meets Judy when he's working as a golf caddy at an upscale country club. This is a great opportunity for the young lad from a relatively modest background to rub shoulders with the rich and privileged. Judy certainly comes from a privileged background herself; she's also a bit of a spoiled brat. When Dexter first meets her, she's throwing a huge tantrum at her nurse. Judy wants a caddy and she wants one now! So she summons Dexter with all the imperious condescension of a queen.

Instead of being repelled at this outburst, as most people would be, Dexter becomes instantly smitten with Judy. Among other things, he's entranced by her incredible passion, so much so that he emulates Judy's willfulness by resigning his job, despite his being universally acknowledged as the best caddy at the club.

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When does Dexter first encounter Judy Jones in F. Scott Fitzgerald's "Winter Dreams"?

Dexter, a very ambitious 14 year-old, much like Fitzgerald's James Gatz who becomes Jay Gatsby, works diligently as a caddy to fulfill his dream of one day becoming rich and famous. However, he abruptly decides to quit his job when he meets Judy Jones, the daughter or a wealthy golfer/club member. Judy, a spoiled 11-year-old girl, wants Dexter to caddy for him and when she spots him on the golf course, she summons him by yelling,

" 'Boy!' " several times.

Dexter is stunned at first because he cannot believe that a girl who was in "bloomers" the year before would address him in such a condescending manner.  When his boss tries to make him caddy for her, he quits his job.

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Under what circumstances does Dexter see Judy Jones for the third time in F. Scott Fitzgerald's story "Winter Dreams"?

It depends on how you organize their encounters.

For certain, Dexter sees Judy for the first time as a child on the golf course when he is caddying and she is there to play.

Also for certain, he sees her for the second time after many years at the same golf course, when they are both there separately to play.

If you count that whole summer and the following year or so as a single encounter, which is probably the best way to organize your thoughts about “Winter Dreams,” then Dexter sees Judy for the third time about a year later. He’s engaged to a girl named Irene, but at the moment Irene isn’t feeling well, so he’s not hanging out with her on this particular night. He’s at the University Club at a dance, standing around, bored, when suddenly he hears a “familiar voice” say “Hello, darling,” and Judy is there, approaching him and wanting to talk and drive around town together. This is when they get back together for the final time, but it’s only for about a month—and that’s it. They never rekindle their romance after that. Even though Dexter ends his relationship with Irene, he never marries Judy—and Judy marries someone else.

But let’s back up. If you’re counting individual encounters and you want to know when Dexter and Judy cross paths for the third time, then let’s go back to that golf game, when we know for certain that they see each other for the second time. In that case, Dexter sees Judy for the third time not long after the game, when he’s floating on his raft on the lake, and she zooms up to him in her motorboat. She’s avoiding a boring date who’s waiting back at her house, and she asks Dexter to drive her boat so she can ride behind it on her surfboard. That’s when they begin their first fling.

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In "Winter Dreams," under what circumstance does Dexter see Judy Jones for the first time?

The story begins with an introduction of Dexter, a caddy, whose father owned the second best grocery store in Black Bear. During the winter, Dexter skied and felt the melancholy of the season. Despite this melancholy, as winter approached again, Dexter would be filled with visions of himself as a golf champion. During one such day dream, Dexter imagines winning easily or coming from behind in dramatic fashion. 

The narrator brings the reader out of that day dream. Dexter informs Mr. Jones that he is too old to caddy. Mr. Jones doesn't want him to leave but Dexter has made up his mind. Dexter hands in his badge and walks home. In the next lines, the reader learns that Dexter's encounter with a young Judy Jones is what prompted him to quit in the first place: 

The little girl who had done this was eleven--beautifully ugly as little girls are apt to be who are destined after a few years to be inexpressibly lovely and bring no end of misery to a great number of men. 

Young Judy Jones is condescending to Dexter, calling him "boy" even though he's three years older than her. Subsequently, Dexter quits. 

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