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Sort the sixteen terms into four categories. The four categories are joined by a common thread, with that being the solution. I think this one will play hard, so good luck!

SQUASH ARTICHOKE EARLY SPRING CUPID'S ARROW
PUPPY LOVE EMPATHIZES ACQUITTAL CROWD SURGE
BLACK HISTORY YOUR STOP PROM NIGHT DEVASTATE
WASHINGTON 5PM ROMAINE AMETHYST
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I think the common theme between the four categories here is:

Valentine's Day (which is today, of course - February 14th...).

The categories should be:

Group 1: A time to 'get off'
5PM (from work), ACQUITTAL (from a criminal charge), PROM NIGHT (with your date), YOUR STOP (when using public transport).

Group 2: Words meaning 'Crush'
CROWD SURGE (a physical crush in a public place like a stadium), DEVASTATE (crush, emotionally), PUPPY LOVE (a romantic crush, typically when young), SQUASH (crush physically).

Group 3: Things that have a heart
ARTICHOKE, CUPID'S ARROW (traditionally depicted as having a heart-shaped head), EMPATHIZES (i.e. cares, or 'has a heart'), ROMAINE (the lettuce, sold in 'hearts').

Group 4: Connected with the month of February
AMETHYST (February's birthstone), BLACK HISTORY (February is Black History Month), EARLY SPRING (the first bulbs and shoots begin to show in February, in the Northern Hemisphere), WASHINGTON (George Washington's birthday).

Considering all of these together...

Valentine's Day is a time to 'get off' (though some might phrase that more tenderly...) with a partner or a crush, is associated with hearts, and is celebrated in February.

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