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What event shocked the boss in "The Fly"?

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The boss in "The Fly" is shocked when Woodifield, his old friend, casually mentions seeing the grave of the boss's son during a visit to Belgium. This unexpected reminder of his son's death in World War I brings back suppressed emotions and sorrow. To cope with his distress, the boss later distracts himself by torturing a fly, highlighting his struggle to manage his grief and the emotional impact of the conversation.

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The answer to this question can be found about halfway through this great short story. Woodifield and the boss are talking with each other and sharing a bit of top shelf whisky. Woodifield is quite pleased to be allowed some of the drink because his family no longer lets him have any of it at home. Soon after commenting on the amazing taste of the drink, Woodifield announces that his daughters took a recent trip to Belgium. While there, they visited the grave of their brother. They also happened to see the grave of the boss's son. Woodifield then comments about how beautifully the cemetery is kept.

"The girls were delighted with the way the place is kept," piped the old voice. "Beautifully looked after. Couldn't be better if they were at home. You've not been across, have yer?"

Woodifield then tells a story about how his daughters felt ripped...

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off by the restaurant/hotel. By this point, the boss isn't listening very closely. He answers without understanding why he is answering.

"Quite right, quite right!" cried the boss, though what was quite right he hadn't the least idea.

The boss then shows Woodifield out, and we are told why the boss essentially shut himself down mentally from the conversation.

It had been a terrible shock to him when old Woodifield sprang that remark upon him about the boy's grave.

The boss never expected their dead sons to come up in conversation. The fact that it was brought up in conversation shocked him quite a bit. It has been many years since their deaths, and the boss has done an effective job of repressing/forgetting the emotional hurt of losing his only son. Unfortunately, Woodifield's comment brought all of those emotions rushing back, and the emotional flooding was a shock to the boss.

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The boss is catching up with his old friend, Woodifield. Both men lost sons in the First World War, and during their conversation Woodifield talks about his daughters' recent trip to Belgium to visit their brother's war grave. The old man appears quite calm and matter-of-fact as he tells the boss about the immaculate, well-kept graves, and how his daughters were ripped-off for a little pot of jam at the hotel where they were staying. He also casually mentions that his daughters saw the grave of the boss's son.

The boss hadn't been expecting Woodifield to remind him of his tragic loss. His remark about his son's grave had come as a bit of a shock to him, stirring up all kinds of unpleasant emotions he'd rather not have to deal with. But deal with them he must, and to take his mind off the immense sorrow he's now feeling he proceeds to torture a fly to death on his desk.

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