The chapter begins with Winston recalling his experience with a prole prostitute he’d met three years ago. As he fills his diary with details of this experience, he wonders about the Party’s hatred of sex. He realizes that the Party regards sexual desire as a detriment, an obstacle to be managed and regulated in the name of the common good. To this end, the Party aims to make sex drab and unappealing to its subjects. According to the Party, the sole purpose of sex is to procreate. Marriages are subject to the Party’s approval; the Party also routinely prevents any union suspected to be based on sexual desire. Accordingly, relationships that are non- or extra-marital are strictly prohibited and harshly punished. On the other hand, when it comes to members of the underclass, the occasional fling is deemed okay and is also exempt from harsh punishment. Orwell also sheds more light on Winston’s past in this chapter.
We find out that Winston’s marriage to Katharine was rather incompatible. Katharine was an ardent follower of the Party’s teachings. There was no pleasure or chemistry in their sexual relationship either. Since their marriage produced no kids, they were eventually able to separate. According to the government, not having kids is the only criterion for separation. Currently, Winston is unaware of Katharine’s whereabouts.
Every few years, Winston’s need for intimate physical contact drives him to the proletarian section of the town. Here he hopes to vent his sexual desire in brief and joyless sexual encounters. Sex is exchanged for either cash or gin. He finds his last encounter particularly disturbing. The woman he finds appealing on account of her painted face and scent turns out to be very old and completely toothless. Despite his surprise and repulsion, he goes through with the act nonetheless.