set one's cap for, to

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set one's cap for

Pursue someone romantically, as in We all thought Anne had set her cap for Joe, but we were wrong. In the 1700s this term, which may have alluded to donning one's best headgear, was applied to members of either sex, but by the early 1800s it generally described a woman chasing a man. It is probably obsolescent.
See also: cap, set
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

set (one's) cap for

To attempt to attract and win as a mate.
See also: cap, set
American Heritage® Dictionary of the English Language, Fifth Edition. Copyright © 2016 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

set one's cap for, to

To pursue someone as a potential mate. This term dates from the eighteenth century, and although at least one writer believes it refers to ladies choosing their most becoming headgear in order to attract gentlemen, it was originally applied to both sexes. By the early nineteenth century, however, it was used mostly for females chasing males, as in Byron’s Don Juan of 1832 (“Some who once set their caps at cautious dukes”) and Thackeray’s Vanity Fair of 1848 (“Have a care, Joe; that girl is setting her cap at you”). Shirlee Emmons’s biography of Lauritz Melchior (Tristanissimo, 1990) says Melchior’s children believed “that Kleinchen deliberately set her cap for this young man who lived alone and far from his family.”
See also: cap, set
The Dictionary of Clichés by Christine Ammer Copyright © 2013 by Christine Ammer
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