In “Winter Dreams,” time brings both promise and despair, fulfillment and loss. Like the image of the falling clock in Fitzgerald’s The Great Gatsby, every moment in “Winter Dreams” comprises its own end.

Dexter looks both forward and backward. He seeks future success while reminiscing about moments that encompass his identity as an all-American success story. While a guest at the Sherry Island Golf Club, Dexter glances “at the four caddies who trailed them, trying to catch a gleam or gesture that would remind him of himself, that would lessen the gap between his present and his past” (664). Dexter revels in the feeling of becoming—the exhilaration of being on the cusp of one state and another. As he lounges by the lake outside of the Sherry Island Golf Club, Dexter recalls a tune that was played at prom “when he could not afford the luxury of proms” (665). The song elicits “a mood of intense appreciation, a sense that, for once, he was magnificently attune to life and that everything about him was radiating a brightness and a glamour he might never know again” (665). Although Dexter is grateful for what he now has and where he is in his life, he recognizes the fleetingness of the moment and the reality that his current state of youth and energy will not last forever.