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At the enchanted metropolitan twilight I felt a haunting loneliness sometimes, and felt it in others – poor young clerks who loitered in front of windows waiting until it was time for a solitary restaurant dinner – young clerks in the dusk, wasting the most poignant moments of night and life. (3.156)
You know all those clichés about big cities being lonely places? Fitzgerald thought so, too. He sees New York as being like one of Gatsby's parties, only less glamorous: full of people, and full of loneliness.
"Your place looks like the World's Fair," I said.
"Does it?" He turned his eyes toward it absently. "I have been glancing into some of the rooms. Let's go to Coney Island, old sport. In my car."
"It's too late."
"Well, suppose we take a plunge in the swimming-pool? I haven't made use of it all summer."
"I've got to go to bed."
"All right." (5.3-8)
Gatsby has a house full of people, and all he wants is one friend to go swimming with him. Talk about lonely.
Thirty – the promise of a decade of loneliness, a thinning list of single men to know, a thinning brief-case of enthusiasm, thinning hair. But there was Jordan beside me, who, unlike Daisy, was too wise ever to carry well-forgotten dreams from age to age. As we passed over the dark bridge her wan face fell lazily against my coat's shoulder and the formidable stroke of thirty died away with the reassuring pressure of her hand. (7.308)
Having seen the wrong end of thirty, Shmoop can assure Nick that it really isn't that bad. But at least he has someone to keep him company, right? Well, yeah—until things start going south and she's out. (But Nick is totally right about all the thirty-something men being married. Just saying.)