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

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amarang9 eNotes educator| Certified Educator

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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Winter Dreams

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