“Winter Dreams”, analysis of the story by Fitzgerald

Plot Summary

Winter dreams are considered to be one of Fitzgerald’s most accomplished short stories. Published in 1922, Winter Dreams is a play on the American Dreams ideal perpetuated in that era and is a study of class, aspirations and relationships and obsessions through infatuation.

Dexter Green is the character around which the story is based. Son of a grocer in Minnesota, Dexter caddies at the local golf course during the Summer months to earn pocket money. Dexter looks up to the golfers that he caddies for with an aspiration of achieving their status and is inspired to better himself. By chance whilst working he meets the leading female character of the story, Judy Jones, who requests that Dexter caddies for him while she plays golf. Dexter is unable to comply due to other caddying commitments, at which point Judy sends out a potential warning signal that Dexter overlooks by striking her nurse who is with her on the golf course in a fit of frustration and anger, a reaction to her request not being fulfilled. Dexter promptly quits his job as a caddy in frustration.

Dexter demonstrates his determination to succeed by this act and it is the first sign of his desire to achieve his ‘Winter Dreams’. Stretching his finances to attend a highly reputable university, Dexter completes his education, borrows money and establishes himself as the wealthy owner of a chain of laundry businesses in the Midwest. Having achieved a very comfortable level of success he moves to New York to progress his social climb.

Dexter and Judy’s paths cross again on the golf course where once again Judy demonstrates a public display of impetuousness and bad manners to other players. But again Dexter overlooks this as he is becoming obsessed with making her his own, taming her perhaps, and establishing himself as a social equal.

After an evening of water skiing together Dexter and Judy agree to dinner at Judy’s where she admits, after asking Dexter’s permission to cry, that a man that she had been dating was not all he seemed and did not have the financial resources to look after her in the manner that she was expecting. Upon being asked Dexter volunteers that he may well be the wealthiest man in the region. Dexter becomes smitten fully but at this stage Judy disappears with another man, frustrating Dexter even further.

Judy has a number of acquaintances with other men and Dexter makes it his mission to attend an event where she may be present, in his ongoing and blinded attempt to woo her and win her affections. Eventually realizing that his quest is in vain Dexter meets Irene and they agree to become engaged. On the evening of the announcement, Irene is unwell and the engagement is postponed, at which point Dexter bumps into Judy yet again by accident. Judy takes this opportunity to discusses their previous passion together and suggests that he should ask her to marry him.

Taking Judy home that evening and having gone inside with her, Dexter falls hopelessly in love with her. It does not occur to him that he has upset Irene and her family by his actions, nor that his professional standing has been tarnished. All that Dexter can see is the love that he has for Judy, not seeing that her perceived love for him back was waning rapidly.

Events occur that force Dexter back to the East with the intention of selling his business. World War 1 breaks out and Dexter launches himself into basic training as something of a distraction from recent events. When he returns aged 32 Dexter learns that Judy has married a man who turned out to be a heavy drinker who cheated on her regularly. He also learns that she has lost her good looks and stays at home daily looking after her children.

Dexter is hit hard by this information he learns from a friend. He is devastated by the loss of her beauty and her personal situation but more importantly, he rues the time that he wasted pursuing his ‘Winter Dream’.

Winter Dreams – Analysis

Winter dreams studies a number of social issues that were prevalent at the time and are still relevant. Dexter Green was born and raised in a modest family environment and from an early age wanted to better himself financially and socially. His time caddying at the golf club gave him two clear insights into life and social status. He wanted to achieve that level of social mobility but simultaneously showed little patience with his perceived superiors and was keen to progress at almost any cost.

This almost blind determination to achieve his goals included having the appropriate wife and in the early stages of their meetings and liaisons Dexter was blind to Judy’s self-serving shortcomings as well as her impatience, arrogance and lack of respect for anyone. Happy to overlook these distasteful traits he blindly pursued her as almost a personal challenge.

Judy was clearly a spoiled and impetuous lady with no patience or acceptance of anything that didn’t go the way she wanted. Her treatment of staff and companions was disgraceful and she relied on her social standing and good looks to maintain what tenuous relationships she had with men. Working through a number of partners she never became satisfied and adopted an ongoing and relentless pursuit for the ideal partner, little realizing that she did not know how he would manifest himself if she ever did meet him. Settling for less than best due to the passage of time, her reputation and her diminishing looks she may well have regretted opportunities.

Winter Dreams is an insightful view of relationships, aspirations, class divides and social climbing. But perhaps, more importantly, it analyses the sometimes blind obsession that comes from infatuation. Had Dexter taken a more holistic view of events and allowed himself to really analyzed who and what he wanted then his Winter Dream may have had a chance to mature.

The book resonates with many people for many reasons, and there are people that will have perhaps been in similar circumstances to Dexter. Likewise, there may be people reading this from Judy’s point of view who realize that sometimes the best opportunities are staring you in the face yet are not instantly seen. Life lessons – certainly. Entertaining, without a doubt. Deep? Yes if you read between the lines.

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