A Pragmatic Analysis of Crossword Puzzle Difficulty
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2015
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Swarthmore College. Dept. of Linguistics
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Thesis (B.A.)
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Abstract
The language of crosswords is intended to trick readers to some degree while still eventually
leading them to the correct answer. While crosswords are governed by fairly strict rules dictating
word length, grid structure, and clue content, clues are often purposefully ambiguous
and provide a level of context that would be insufficient for normal conversation. In many
newspapers, including the New York Times, daily puzzles become more difficult as the week
progresses. For a puzzle later in the week, the creator may assume that solvers are seasoned
enough to know the basic crossword patterns and can begin to play with conventions.
This thesis explores how the methods by which crossword creators write difficult clues
mirror the Gricean maxims. It breaks down crossword entries into several difficulty factors:
requirement of cultural knowledge, obscurity, ambiguity, underspecificity, and trickiness.
Each of these factors is explored at length and then analyzed quantitatively using a large
data set of entries from New York Times crosswords.
My findings indicate that many of these factors are interrelated. The distinction
between puzzles at each day of the week is more nuanced than some abstract, monotonically
increasing "difficulty" function. Some of the factors tum out to not be highly correlated to
difficulty at all. In some cases, clues later in the week appear to favor entertainment value
over sheer difficulty level.
Additionally, I show how pragmatic theories can be applied to a highly restricted and
unnatural form of communication. My work extends similar research into the use of Gricean
maxims in jokes and advertisements. This thesis combines natural language processing
approaches on a full corpus with detailed manual analysis, demonstrating that computational
methods can be used to address an area such as pragmatics.