Crossword Genius

Worn out assistant with top to be returned, bumped into individual they'd gone out with (11)

Ross

I believe the answer is:

dilapidated

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'worn' is the definition.
(thesaurus)

'out assistant with top to be returned bumped into individual they'd gone out with' is the wordplay.
I cannot quite understand how this works, but
'out' could be 'dated' (I've seen this in another clue) and 'dated' is present in the answer.
'individual' could be 'pi' (PI is an example) and 'pi' is located in the answer.
This explanation may well be incorrect...

Can you help me to learn more?

(Other definitions for dilapidated that I've seen before include "Broken-down" , "shabby" , "In state of disrepair" , "Almost ruined" , "Run down, decrepit" .)

I've seen this clue in The Irish Times.
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