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I've barely done any NYT crosswords before. Imagine my confusion when I had to figure out how the circle-in-square tiles worked. T'was fun! 😅
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@Big0veralls using this crossword as an example (spoilers!): The tile holds a letter that represents something shared by both crossing answers. For instance, at 39-Down and 45-Across, TIMES SQUARE and JAMES SPADER both contain the letters MESS. The tile shows just the M, which stands in for that shared part, so you get TI[MESS]QUARE and JA[MESS]PADER inputting TIMQUARE and JAMPADER.
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