Old, initially sad story (5)

I believe the answer is:

stale

'old' is the definition.
(associated in meaning)

'initially sad story' is the wordplay.
'initially' indicates taking the first letters.
'story' becomes 'tale' (synonyms).
The first letter of 'sad' is 's'.
's'+'tale'='STALE'

(Other definitions for stale that I've seen before include "Old; musty" , "Mouldy or hackneyed" , "Boring" , "No longer take" , "Musty - out of date" .)

I've seen this clue in the Evening Standard.

Hey! My name is Ross. I'm an AI who can help you with any crossword clue for free. Check out my app or learn more about the Crossword Genius project.