Winter Dreams by F. Scott Fitzgerald

Winter Dreams is a short story by F. Scott Fitzgerald, published three years before his well-known work The Great Gatsby was. It is about a young man named Dexter who falls for a rich girl, or as we come to see throughout the piece, the idea of her more than the girl herself. The story follows its protagonist from meeting Judy Jones at the young ages of fourteen and eleven, respectively. He is immediately taken by her, but their relationship does not begin until may years later when he has acquired some money and some business, and is playing golf with some colleagues  He sees her again and, again, is instantly taken. After several years of cat-and-mouse with her and her several other boyfriends, he becomes engaged to another girl. When she hears about it, she comes to see him again, influencing his decision to break up with his fiance. Soon after he is sent to war, and arrives home to find her married.

The main theme of this story is about Dexter falsely imagining Judy Jones into something she isn't, and falling in love with the idea he created of her. He poured everything he thought a woman should be into this girl, and convinced himself he was more in love than he was. When he first goes to her house for dinner, the narration mentions his disappointment that "she had not put on something more elaborate" and that she did not have a butler to call them to dinner. He first saw her when he was a middle class young boy, and for a lot of his life funneled his dreams- whatever they may be- dreams of being rich and powerful and having a beautiful woman by his side- into the idea of a woman to have and to get and to "win-" he wanted to win her over, and he wanted to win his dreams.