to set one's cap at
- idiom
- Archaic
- She is trying hard to set her cap at the new teacher, hoping to win his affection.
Examples
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Didn't I tell you that Blanche had set her cap at him?
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Why set your cap at Willoughby when you've already made such a conquest?
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After months of flirting, he finally decided to set his cap at his longtime crush.
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It's clear that she has set her cap at that charming gentleman at the party.
Synonyms
To try to start a romantic relationship with someone
Try to show romantic or sexual interest in someone by making advances
To try to win someone's love, often to form a serious relationship
To try to begin a romantic relationship with someone
Say you want to marry someone and ask them to marry you
Antonyms
How Interested
Surface Forms
Morphology
set + one's + cap + at
The meaning 'to try to attract or pursue someone' cannot be derived from the literal parts 'set' (put), 'one's' (possessive), 'cap' (hat) and 'at' — there is no obvious compositional link between placing a hat and courting. This is an archaic, culture-specific idiom whose historical signaling of romantic interest is not transparent to a B1 learner, so the expression is unpredictable from its constituents.
Etymology
The idiom set one's cap at may come from an old custom where a woman would set her cap toward a man she liked, a small hat signal that showed her interest. So, it came to mean 'to try to attract or win someone', often with the idea of 'to marry'.