| Quote #1
When he was twenty-three Mr. Hart – one of the gray-haired men who like to say "Now there's a boy" – gave him a guest card to the Sherry Island Golf Club for a week-end. So he signed his name one day on the register, and that afternoon played golf in a foursome with Mr. Hart and Mr. Sandwood and Mr. T.A. Hedrick. He did not consider it necessary to remark that he had once carried Mr. Hart's bag over this same links, and that he knew every trap and gully with his eyes shut – but he found himself glancing 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 which lay between his present and his past. (2.4)
Dexter is a self-made man: he has used his wits to make a fortune. However, the implication of the term "self-made man" is that you have made yourself from scratch, that you have no origin point except your own talents and skills. So the new Dexter is, quite literally, a different man from the kid who used to caddy at the Sherry Island Golf Club. No wonder he is having some trouble with "the gap which lay between his present and his past."
| Quote #2
The tune the piano was playing at that moment had been gay and new five years before when Dexter was a sophomore at college. They had played it at prom once when he could not afford the luxury of proms, and he had stood outside the gymnasium and listened. The sound of the tune precipitated in him a sort of ecstasy and it was with that ecstasy he viewed what was happening to him now. It was a mood of intense appreciation, a sense that, for once, he was magnificently attuned to life and that everything about him was radiating a brightness and a glamour he might never know again. (2.28)
As Dexter lies out on the raft in the middle of Black Bear Lake, it's as though he has found some way to bring together his poorer past self and his rich present self. Listening to the music, he can remember that pure appreciation of the life he wants. This is one of the few moments in "Winter Dreams" when Dexter finds his past life and his present life in harmony. What makes that possible? Will he ever have this feeling again?
| Quote #3
In then, with a rustle of golden cloth. He slammed the door. Into so many cars she had stepped – like this – like that – her back against the leather, so – her elbow resting on the door – waiting. She would have been soiled long since had there been anything to soil her – except herself – but this was her own self outpouring. (4.35)
We know that Dexter has a definite past he doesn't want people to remember, as a caddy at the Sherry Island Golf Club. But somehow, Judy does not seem to have a past that she wants to deny. Even though she has had many love affairs, none of them have left her with a bad reputation. How did she get away with that?