The squadron finally receives the go-ahead to bomb Bologna, but by this time Yossarian does not feel like going over the target even once. He pretends that his plane’s intercom system is broken and orders his pilot, Kid Sampson, to turn back. They land at the deserted airfield just before dawn, feeling strangely morose. Yossarian takes a nap on the beach and wakes up when the planes fly back. Not a single plane has been hit. Yossarian thinks that cloud cover must have prevented them from bombing the city and that they will have to make another attempt, but he is wrong: facing no antiaircraft fire, the Americans bombed the city without incurring any losses.
Captain Piltchard and Captain Wren ineffectually reprimand Yossarian and his crew for turning back and inform the men that since they missed the ammunition dumps the first time, they will have to bomb Bologna again. Yossarian confidently flies in, assuming there will be no antiaircraft fire, and he is stunned when shrapnel begins firing up toward him through the skies. He furiously directs McWatt into evasive maneuvers and fights with the strangely cheerful Aarfy until the bombs are dropped. Yossarian does not die—though many other men in the squadron do—and the plane lands safely. Yossarian heads immediately for emergency rest leave in Rome.
Luciana is a beautiful Italian woman whom Yossarian meets at a bar in Rome. After he buys her dinner and dances with her, she agrees to sleep with him, but not right then—she will come to his room the next morning. She does, but then angrily refuses to sleep with Yossarian until she cleans his room, disgustedly calling him a pig. Finally, she lets him sleep with her. Afterward, Yossarian falls in love with her and asks her to marry him. She says she won’t marry him because he is crazy; she knows he is crazy because no one in his right mind would marry a girl who was not a virgin. She tells him about a scar she got when the Americans bombed her town.
Suddenly, Hungry Joe rushes in with his camera, and Yossarian and Luciana have to get dressed. Laughing, they go outside, where they part ways. Luciana gives Yossarian her number, telling him that she expects him to tear it up as soon as she leaves because she thinks that he is impressed with himself that such a pretty girl would sleep with him for free. He asks her why on earth he would do such a thing. As soon as she leaves, though, Yossarian, impressed with himself that such a pretty girl would sleep with him for free, tears up her number. Almost immediately he regrets doing so, and, after learning that Colonel Cathcart has raised the number of missions to forty, he makes the anguished decision to go straight to the hospital.
In this section, the disordered chronology functions as an instrument for building suspense. The lengthy digression about the Great Loyalty Oath Crusade interrupts the tense buildup to the Bologna mission, which occurs shortly before the scene at the beginning of the novel, when the number of required missions is still thirty-five. The Great Loyalty Oath Crusade story is ironic and funny; the Bologna mission is a dismal story told in terms of endless rain and growing worry. By breaking off the Bologna story in the middle to tell the exaggerated parable of the Loyalty Oath Crusade, Heller heightens the sense of uncertainty and anticipation surrounding the outcome of the Bologna mission. During the description of the actual bombing run to Bologna, however, Heller devotes a chapter almost entirely to a single event, without his usual digressions. This very detailed, vivid account of the attack makes time appear to move more slowly, trapping the reader in the same drawn-out terror as the characters. The earnest, straightforward manner in which the Bologna story is told is a signal that we are meant to take this episode seriously—that there is nothing funny about this aspect of war.
Although Catch-22 is written mostly from the perspective of a third-person narrator who describes what each of the characters is thinking, we hear mostly what is happening in Yossarian’s mind, and many of the observations about the absurdity of the war seem to be his own. So, despite the fact that each chapter of Catch-22 bears the name of a character described in that chapter, the narrative generally returns to Yossarian. A significant departure from this organizational method occurs in the chapter entitled “Bologna,” however: instead of operating as a largely humorous description of the nature and history of one of the novel’s characters, this chapter remains almost entirely in the present of the story, and Yossarian is forced to confront his desire to live at the expense of everything else. The chapter title itself—a place name rather than a person’s name—marks a shift from a satirical and humorous focus on the unwitting characters engaged in the war to a serious focus on the present reali-ties of the war.