- Angst? What Angst?: Leigh gets over Dad getting Bandit instead of him in the span of about fifteen seconds. It's kinda-sorta justified in that Leigh wants his dad to be happy, and also wants Bandit to be happy, but still...
- First Installment Wins: The sequel, Strider, is much, much less well known than the original novel; it won no awards at all.
- Protagonist Title Fallacy: Leigh is the novel's protagonist, with Mr. Henshaw being more of a device to move the plot along than anything.
- Retroactive Recognition: Pedro Pascal recorded audiobooks for both Dear Mr. Henshaw and Strider, years before starring in such works as Narcos and The Mandalorian.
- Sequelitis: Again, the decidedly mediocre Strider.
- Tear Jerker:
- Leigh's parents deciding not to get back together at the end, especially considering that Leigh really hoped they would.
- The scene with "the Pizza Boy". The ambiguity only makes it worse, not better.
- Leigh not getting to keep Bandit at the end, even if it was his own idea, and he was pretty chill about it.
- The Woobie: Leigh, oh so much. Bonnie counts as well, as she's obviously distraught over how her relationship with Bill turned out.
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