Nick starts this chapter by listing all the guests who attended one particular party at Gatsby’s. It’s a fairly comprehensive list, divided into groups from East Egg and West Egg and detailing what exactly made these guests important. One guest was notable for being brother to a man who strangled his wife. Another is well-known for staying so long at Gatsby’s parties as to be considered a “boarder.”

None of these people, of course, know their host well enough to really be considered his friends, and Nick doesn’t seem to think highly of them. He lists them only to indicate to the reader that all Gatsby’s parties were attended by the rich and glamorous. This gives them a sheen of importance and, also, of superficiality. Painting a picture of the residents in both East and West Egg provides insight on the divide between old and new money. 

Nick doesn’t really get to know Gatsby until he drives up one day and invites him to lunch out of the blue. Together, they drive into the City, discussing Gatsby’s past, and Nick realizes that Gatsby likely isn’t an Oxford man as he often claims to be. At one point, Gatsby even makes the mistake of saying San Francisco is in the Midwest. This makes Nick suspicious of Gatsby, but no less interested and not unwilling to forgive him for lying, because the way he does it is so awkward and insecure that it seems he’s desperate for Nick to like him; and then of course there are some parts of his story that are true. He really does have a medal from Montenegro, where he fought in World War I, and he really did go to Oxford. He even has a picture to prove it.

Having earned some of Nick’s trust, Gatsby asks him to speak with Jordan Barker, who will tell him something important; but Gatsby won’t say what that thing is or explain why he needs Jordan to tell Nick about it for him. So by the end of their drive Nick isn’t sure what to think or why Gatsby’s being so cryptic.

Only during lunch does Nick understand that Gatsby needs to lie about certain things in order to protect himself. He’s involved in the bootlegging business, just like everyone says, and has a “friend,” Mr. Wolfsheim, who is a prominent figure in the New York City underworld and who runs the business Gatsby profits from.

Gatsby brings Nick to lunch with Wolfsheim in order to earn Nick’s trust. He seems to think that, if he shows Nick a fraction of the truth, then he’ll be more inclined to help him later. He happens to have a favor he wants to ask, but he can’t do it until Nick trusts him, feels sorry for him, and hears the story that Jordan tells him later that afternoon. It’s sensitive in nature.

Fitzgerald dips into Jordan’s perspective to tell us the story of how Gatsby and Daisy first met. It was back in 1917, when Jordan was sixteen and Daisy was eighteen. Gatsby was just a young military officer in a clean white uniform. Jordan happened to walk by Daisy’s house one morning and saw them sitting in Daisy’s car, speaking very intimately.

She wasn’t friends with Daisy then and didn’t know all the details of their affair, but did hear through the town’s rumor mill that Daisy wanted to go up to New York to say goodbye to Gatsby before he was shipped off to war, but her family wouldn’t let her. It seems that Gatsby wanted to marry her, but Daisy wouldn’t consent to it because he was poor and didn’t seem to have a future. Soon after, she got engaged to Tom and seemed to be happy.

Then, the day of her bridal dinner, she received a letter from Gatsby and nearly called off her engagement; but the next day she married Tom and left for a three-month vacation. When Daisy got back, Jordan says, she was crazy about her husband, and everything appeared to be well; then Tom started cheating on her, and their marriage began to sour. It wasn’t until Daisy heard Gatsby’s name at that first dinner that she realized Gatsby was in town. Jordan hadn’t made the connection.

When the narrative switches back to Nick’s perspective, it’s later that same day, and Nick and Jordan are still in New York. Jordan asks Nick for the favor Gatsby wants: to let him and Daisy meet at his house. Nick tacitly agrees and in the light of a street sign draws Jordan to him and kisses her.

Allusions

1919 World Series. This was the last World Series without a Commissioner of Baseball. It’s believed to have been “fixed” or rigged by a ring of gamblers who conspired with members of the Chicago White Sox to intentionally throw games. This scandal is commonly referred to as the Black Box Scandal.

If Meyer Wolfsheim is really behind this scandal, as Gatsby claims, then he’s a very powerful and very dangerous person. Gatsby would be wise to extricate himself from any and all of their business dealings. Fitzgerald uses the danger Gatsby faces to both call into question his life choices and elicit sympathy from the reader.

Hotel Metropole and Rosey Rosenthal. The Hotel Metropole on West 43rd Street, right by Times Square, where Herman Rosenthal, a small time bookmaker, was gunned down by members of the Lenox Avenue Gang in July of 1912. Rosenthal’s murder was widely believed to have been ordered by Lieutenant Charles Becker, one of three police officers in the case against Rosenthal.

The subsequent trial, in which five men (including Becker) were convicted and executed, proved so complex that it stopped and then started up again two years later after police could investigate the crimes in greater detail. Wolfsheim indicates that he was in the Hotel Metropole at the time of the murder and that this makes it too painful for him to eat lunch there. This allusion cements the reader’s idea of him as an underworld figure and implies that the Metropole may have been a place frequented by crime lords like Wolfsheim.

“The Sheik of Araby.” A jazz standard composed in 1921 in response to Rudolph Valentino’s performance in the hit silent film The Sheik. Fitzgerald quotes a few lyrics from the song near the end of this chapter, when Nick and Jordan leave the Plaza and walk New York City’s streets. He uses the song to evoke the mood and feeling of the Jazz Age, but may also be using the lyrics “I’m the Sheik of Araby. / Your love belongs to me” to characterize Gatsby’s love of Daisy as possessive and a little unhealthy.

Von Hindenburg. Paul Von Hindenburg, second President of Germany, was Chief of the German General Staff from 1916 to 1919, at roughly the time when Gatsby met Daisy and left to fight in the war. One of the guests at Gatsby’s Sunday morning gatherings mentioned Von Hindenburg as a way of suggesting that Gatsby has unsavory connections to the Nazi regime. These allusions taken together underscore the pervasive fear and distrust of Germans in America at that time.

Character Development

In this chapter, we see how reckless decision making has led the main characters (Daisy and Tom in particular) to their current predicaments. Daisy made the snap decision to marry Tom after receiving Gatsby’s letter and nearly calling the wedding off. Tom begins having an affair almost immediately after returning from his wedding trip. Gatsby, meanwhile, has been doing business with Wolfsheim, which is perhaps the most dangerous decision of all. It seems every character in this book has made terrible life choices, including Nick, who, in moving to New York City, has exposed himself to a lifestyle that he professes to disdain.

It is also important to point out the fact that characters such as Wolfsheim are characterized by racial and cultural sterotypes imposed upon them by white Americans. Wolfsheim, who is Jewish, is characterized as evil, dangerous, and greedy, especially when it comes to money. Physically, he is seen by Nick as a stereotype, as seen with his "small, flat" nose, "tiny eyes," and overall sense of "darkness."

Important Motif

Music. In addition to “The Sheik of Araby” and “Jazz History of the World”, there are many references to music in the novel, which describes names as “melodious,” car horns as “three-noted,” and Daisy’s voice as “full of money.” These sounds and musical notes enhance the lively mood of the party scenes and reinforce the fact that this novel is set during the Jazz Age.

Symbols

Cars. Fitzgerald characterizes people through the description of their cars. Gatsby has what Nick calls a “gorgeous yellow car” (yellow having been previously associated with wealth and luxury), whereas Daisy drove a white roadster when she was eighteen and started dating Gatsby.

Their cars are symbols of their social status and reflect their personalities. That Daisy no longer drives a car of her own after marrying Tom emphasizes the fact that she isn’t a free woman and has to rely on men to travel. That Tom rips the front wheel off his car while driving around with a conquest of his equates him with the drunken party guest in Chapter II who crashes a car with Owl Eyes in it. This is, of course, not a very flattering comparison.

Flowers. Picking up on Daisy’s earlier description of Nick as “a rose, an absolute rose,” Fitzgerald uses flowers in this chapter both as symbols and as tools of characterization. A number of Gatsby’s party guests have “the melodious names of flowers.” When a hearse passes, it’s “heaped with blooms.” Daisy’s home in Louisville has the biggest lawn and, presumably, the most beautiful flowers. In this way, flowers become symbols of life and death as well as the ways in which a lavish lifestyle is a mask for the depressing, dark emotions that are sweeping America at this time.