A History of Short Words

From the New York Times Crossword Puzzle

WOO

Wed, 2 Apr '25
Try to win
Wed, 12 Mar '25
Court
Thu, 27 Feb '25
Try to win over
Sun, 11 Aug '24
Romance
Thu, 11 Jan '24
Try to see?
Thu, 29 Jun '23
Sweet-talk, maybe
Sat, 29 Apr '23
Court
Thu, 6 Apr '23
Seek favor with
Wed, 11 Jan '23
Pursue romantically
Fri, 2 Sep '22
Romance
Fri, 6 May '22
Court
Sun, 23 Jan '22
Court
Mon, 11 Oct '21
Try to win over romantically
Mon, 1 Mar '21
Ply with chocolates and roses, say
Tue, 29 Dec '20
Sweet-talk and send chocolates, say