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Tear Jerker / All the Wrong Questions

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As a Moments subpage, all spoilers are unmarked as per policy. You Have Been Warned.

It's not exactly a Lemony Snicket series if it doesn't have its own doses of sad moments.

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     Who Could That Be At This Hour? 
     When Did You See Her Last? 
  • Near the end of When Did You See Her Last? the book seems to end on a surprisingly positive note for a Snicket story; Cleo’s been found, Ellington's escaped. Then Snicket remembers that Hangfire's still on the loose—and all the horrible plans he seemed to have in mind (including child shackles)— and admits to himself that he doesn't really know what to do, or where he belongs. Then he goes home and tries to cry himself to sleep next to his drunken chaperone. The next morning he gets what's probably the worst news he's ever had. His sister has been arrested because she couldn't lift the hatch on her own.
     Shouldn't You Be In School? 
  • Ellington, just, flatout bursting into tears when she unexpectedly sees a picture of her father. It's a sobering reminder that for all of the trouble and deceit, she's still a lonely young girl who's stuck in a horrible situation, and just wanted her father back.
    • Snicket hid it, but he had cried as well. Worse, if you had been theorizing, or had read the final book and reread this part because you know why he was crying: at this point he knows Hangfire is Armstrong Feint, and this situation was nothing short of downright cruel and devastating.
  • The book is full of these, but the very end of the book hits particularly hard with a reminder of the choices Lemony has had to make and how they've impacted not only him but also Kit:
"[...]Ellington Feint is just trying to rescue a member of her family. She would do anything and everything. I would do the same if I were in her position."
Josephine stopped walking. "No, you wouldn't[.]"
     Why Is This Night Different From All Other Nights? 
  • In Why is This Night Different From All the Other Nights?, his last conversation with Ellington, after Hangfire dies.
    It doesn't matter if you never see someone again, I told myself. There are millions of people in the world, and most of them never see each other in the first place. You hoped to know Ellington Feint forever, but there's no such thing as forever, really. Everything is much shorter than that.
  • At the end of the series, Lemony's friends break away from him. It's understandable—they've just witnessed him commit a horrible act—but it's still very painful to see, especially after all the sacrifices he made to keep them and the town safe. Even worse, this sort of rejection is merely a taste of the exile will come to experience as an adult.
    "What's the news, Moxie?" I asked quietly, but she just shook her head and turned away. Her expression was grim, and her eyes looked dark and haunted like the dead windows of so many buildings in town. I looked from her to the others, and everywhere it was the same. Friend or enemy, associate or stranger, they all shrank from me.
  • The sudden murder of Dashiell Qwerty, one of the nicest and most helpful people in the franchise. When the other characters are told, they're just as sad and horrified as the readers.

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