A History of Short Words

From the New York Times Crossword Puzzle

HINT

Sun, 3 Dec '23
Inkling
Sat, 2 Dec '23
When doubled, comment made with a wink
Sun, 5 Nov '23
Pointer
Sat, 8 Oct '22
Touch
Thu, 6 Oct '22
With 35-Down, some common attire for cooks
Sat, 13 Aug '22
Leave a small tip
Thu, 5 May '22
When doubled, not-so-subtle nudge
Thu, 22 Apr '21
Bit of help