and a part of his ambitions for a better life, is "no longer." It is a sort of death for him, an irrevocable piece of his own past, and thus a watershed. Tied to a youthful and beautiful Judy was an ambitious and determined Dexter, and he realizes that those two people have passed from the world into memory.

As a young man, Dexter is ambitious and determined. He dreams of being more than just a caddy. He has "winter dreams" of a better life. The narrator adds that he is not a snob, but he does have a desire for an upper class kind of life: 

Often he reached out for the best without knowing why he wanted it---and sometimes he ran up against the mysterious denials and prohibitions in which life indulges. It is with one of those denials and not with his career as a whole that this story deals. 

Dexter had this urge to reach out for something better or something higher. Perhaps, this is simply his understanding of what it means to reach for the American Dream. He associates Judy's looks and money with the upper class and the glittering world of his aspirations.

Judy's looks fade as she gets older. When Dexter learns of this, he comes to the realization that her beauty is/was superficial and fleeting. Likewise, the glittering world of the elite social class she belonged to also became quite superficial to him. Dexter has an epiphany that this once evocative, fantastic world of his dreams had always been superficial, shallow, and fleeting. It leaves him feeling empty that this dream is gone now because he sees that there was never any substance in it. 

When Dexter Green first sees Judy Jones, she is only eleven; however, he is struck by the beauty of this girl and "winter dreams" of attainable beauty and of being rich begin to dictate his life. For the first time, Dexter begins to "reach out for the best without knowing why"; he wants "the glittering things." Much like Jay Gatsby of Fitzgerald's novel, Dexter believes that if he attains those "glittering things," he can then have whatever he wants. 

After Dexter becomes wealthy from owning a large chain of laundries, he goes to the Sherry Island Golf Club and plays with some pretentious men. When one of the men loses his ball in the rough, "an enormous thing" happens to Dexter:  he encounters again the beautiful Judy Jones, who "plays through" her golf ball that has come flying past them. Later that day, Judy passes by him in a motor-boat; she invites Dexter to drive it so that she can ride her surfboard behind, and "for the second time, her casual whim gave a new direction to his life."

The next evening Dexter has a dinner date with Judy at her home. After dinner they sit alone on the sun-porch because her parents are gone. Judy explains her "moody depression" during the meal as caused by a man's revelation to her of his poverty when she had not suspected it, and it only shocked her because he had concealed it. As the evening continues, she kisses Dexter and he decides "that he had wanted Judy Jones ever since he was a proud, desirous little boy."

Further, Dexter "surrendered a part of himself to the most direct and unprincipled personality" he has ever encountered; he becomes one of many who receive attention from this beauty. As a result, Dexter becomes frustrated and dissatisfied. When he asks her to marry him, she replies emptily about someday,yet Dexter continues to find her desirable. After a while, he realizes that Judy has become indifferent to him, so he becomes interested in Irene Scheerer as a substitute for his loss, and eventually he proposes to her.

One night when Irene has a headache that puts her to bed, Dexter stands casually in a doorway at the University Club and Judy appears as part of a warm breeze that blows through the room; Dexter "could have wept at the wonder of her return" because everything that was mysterious had left with her; Judy is yet associated with all Dexter's "winter dreams." As they talk, Judy confuses Dexter by saying, "I wish you'd marry me" even though she knows of Irene. Overcome with emotion that his "beautiful, his pride" has returned, Dexter again surrenders to the dreamlike hold Judy has upon him, and he enters her house when she invites him after driving her home.But, Dexter cannot keep her and Judy terminates their engagement. So, he enters the war with a sense of relief, "welcoming the liberation from webs of tangled emotions."

Seven years pass and Dexter has relocated in New York. One day a man named Devlin comes to the office on business; coincidentally, this man's best friend has married Judy Jones. Devlin tells Dexter that Judy was once very beautiful but having a husband who acts "outrageously" has had an affect upon her. As Devlin describes the mundaneness of Judy's life now, Dexter becomes aware that a "sort of dullness settled down" upon him. "The dream was gone." An animation is taken from Dexter and he can never return to it; Dexter cries at the loss, knowing that he "could never go back any more" to his youthful illusions:

Even the grief he could have borne was left behind in the country of illusion, of youth, of the richness of life, where his winter dreams had flourished.

An emptiness strikes at the core of Dexter as that idealization of beauty and love is now gone.

The short story "Winter Dreams" by F. Scott Fitzgerald tells of a boy, the son of a local grocery store owner, who starts off as a golf caddy but aspires to become rich, talented, and highly esteemed. Eventually he becomes prosperous, thanks to a thriving laundry business, and he pursues a relationship with a wealthy young woman named Judy Jones.

In the first part of the story, Dexter meets Judy on the golf course when he is fourteen and she is eleven. As Judy arrives, her nurse is carrying her clubs, but they are looking for a caddy to take over for the nurse. There are several exchanges between the nurse, Dexter, and Judy, and they lead up to a momentous decision that Dexter makes on the spur of the moment.

After Judy and the nurse approach the caddy house, Judy makes a few comments, and then the nurse says, "I don't know what we're supposed to do now." A moment later, Dexter laughs and starts to walk away. Judy calls him "boy" in a tone that probably makes Dexter feel like she considers him to be just another servant.

Judy inquires about the golf teacher and the caddy-master, but Dexter replies that neither is available. The nurse, obviously flustered and ill-at-ease, responds.

"We'd like to get a caddy," said the nurse. "Mrs. Mortimer Jones sent us out to play golf, and we don't know how without we get a caddy."

At this point, Judy gives the nurse "an ominous glance," and when Dexter states that he has to stay by the caddy house until the caddy-master comes, Judy and the nurse start arguing. Judy gets angry; first she hits a golf club on the ground, and then she tries to hit the nurse with it, but the nurse twists it out of her hands. Inwardly, Dexter sides with Judy against the nurse. "He could not resist the monstrous conviction that the little girl was justified in beating the nurse." He may feel this way because in his dreams and ambitions, he already considers himself to be a member of the upper class.

The caddy-master then shows up, and the nurse says, "Miss Jones is to have a little caddy, and this one says he can't go." Dexter repeats that he has been instructed to remain by the caddy house, but the caddy-master instructs him to go caddy for Judy. Judy's smug response is to drop her bag and walk off in a "haughty mince." Dexter, in turn, reacts by quitting his job. He does this because Judy has made him feel like one of her servants, and his "winter dreams" of prosperity will not allow him to be put in that position. The character traits that cause him to act this way are ambition, determination, and a sense of self-importance.

Dexter is normally a very down-to-earth guy, not someone who loses control of himself or overindulges in food, alcohol, or drugs. But when he finds out that Judy is no longer beautiful, for the first time in his life, he feels like drowning his sadness in alcohol:

A sort of dullness settled down upon Dexter. For the first time in his life he felt like getting very drunk. He knew that he was laughing loudly at something Devlin had said, but he did not know what it was or why it was funny.

Dexter's acquaintance has just reported that Judy is no longer a great beauty, that she looks just "okay" now, and that she's "faded" from the stunning, enchanting woman that she always was, ever since the tender age of eleven or so when she first charmed Dexter on the golf course. This news about Judy doesn't simply make Dexter sad; it destroys him and everything he'd dreamed about in his life. For him, Judy wasn't just a beautiful woman; she was beauty itself.

So you can forgive Dexter, or excuse his impulse, when he realizes he wants to use alcohol to erase the pain of this realization. In the context of other characters in Fitzgerald's body of work--that is, compared to the other young men and women in Fitzgerald's stories who indulge regularly in all kinds of excesses, including alcohol--Dexter remains an outlier, someone who typically exhibits self-control and moderation.

You can read more about these characters here to get a deeper understanding of why Judy's beauty is so important to Dexter.