A History of Short Words

From the New York Times Crossword Puzzle

DRIP

Wed, 25 Oct '23
Boring person
Thu, 1 Jun '23
Possible cause for insomnia
Fri, 25 Nov '22
Problem for a plumber
Sun, 30 May '21
Good fashion sense, in modern slang
Sat, 6 Mar '21
Leak proof?
Mon, 11 Jan '21
What melting ice cream cones do