set one's cap for - Phrases/Idioms
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.
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.