Did flirt ruffle Daisy's skirts with toe? (5)
I believe the answer is:
toyed
'did flirt' is the definition.
('toy' can be a synonym of 'flirt')
'ruffle daisy's skirts with toe?' is the wordplay.
'ruffle' indicates anagramming the letters (I've seen 'ruffled' mean this).
'skirts' says to hollow out the word (remove centre letters) (retain the edges).
'with' is a charade indicator (letters next to each other).
'daisy' with its middle taken out is 'dy'.
'dy' after 'toe' is 'toedy'.
'toedy' with letters rearranged gives 'TOYED'.
(Other definitions for toyed that I've seen before include "Played" , "Trifled (with someone's affections)" , "fiddled" , "Engaged in an activity, but not seriously" , "Acted idly" .)