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The sentence is in a letter by Thomas Jefferson, where he describes the agonies of love. I don't understand the meaning: is he fine or not?

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    Can you post the entire sentence, please?
    – stangdon
    Jun 16, 2023 at 13:45

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Context is everything here. Usually, "in a pretty trim" would mean in a good condition, well-balanced, a boat that's all ready for sailing; but in this case, it means just the opposite. The surrounding lines are:

Seated by my fire side, solitary and sad, the following dialogue took place between my Head and my Heart.

Head. Well, friend, you seem to be in a pretty trim.

Heart. I am indeed the most wretched of all earthly beings. Overwhelmed with grief, every fibre of my frame distended beyond it’s natural powers to bear, I would willingly meet whatever catastrophe should leave me no more to feel or to fear.

The Heart's reply shows us exactly what the Head meant - that the Heart is in an awful condition. You could think of "you're in a pretty trim" in this case as being equivalent to "you're in quite the state".

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  • More so a few centuries ago, perhaps, but pretty, like fine, is still closely associated with satirical negative assessments. This is a fine state of affairs - we're in a pretty pickle now! Jun 16, 2023 at 17:24
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    @FumbleFingers - yes, we can say satirically 'this is a pretty kettle of fish' about a notably muddled or awkward state of affairs. Jun 16, 2023 at 17:51
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Without the full context of Jefferson's letter being in "pretty (or good or fine) trim" usually means being clean, well maintained and / or smart. It is mostly applied to vehicles in good condition. For example ships, cars, trains and aircraft. Often use by used car salesmen to describe their wares.

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