What circumstances cause Winston's varicose ulcer to bother him in 1984 by George Orwell?
Winston's varicose ulcer actually bothers him more than twice, but each time it does so coincides with him breaking away from the strict regimentation of Party life. The first time it begins itching "unbearably" in the novel, Winston is trying to think of what to write in his journal and coming up blank. The second time is when Winston wakes from his dream of the golden country and has to get up for his morning exercises. After the dream, he has a coughing fit, which causes his ulcer to start itching. The third time, Winston is trying once again to write in his journal when the ulcer starts up. The fourth time, it is "throbbing" because Winston has been walking around the streets of the city by himself. This is transgressive, as Party members are not supposed to do anything on their own. What Winston is doing is called "ownlife" and is considered eccentric. Further, Winston has been thinking about the past, the "half-forgotten" world of his childhood. Finally, after Winston has been tortured by O'Brien, the ulcer becomes "inflamed" again, although it doesn't particularly seem to bother him this time.
If we look at the instances that the ulcer itches or becomes inflamed before Winston's arrest, there is a pattern that it occurs at times Winston is either doing or thinking something that violates Party orthodoxy: writing in his journal, dreaming of the golden country, trying to remember his childhood, or tramping around the city on his own. There seems little doubt that the itching ulcer is triggered by the anxiety his actions cause him as he transgresses the unspoken rules he has internalized.