Most gentle maiden that is hugging disheartened lad on street (7)
I believe the answer is:
mildest
'most gentle' is the definition.
('mild' can be similar in meaning to 'gentle')
'maiden that is hugging disheartened lad on street' is the wordplay.
'maiden' becomes 'm' (cricket abbreviation).
'that is' becomes 'ie' ('i.e.' can be a synonym of 'that is').
'hugging' is an insertion indicator.
'disheartened' says to hollow out the word (remove centre letters).
'on street' becomes 'st' (I've seen this in other clues).
'lad' with its middle taken out is 'ld'.
'ie' going around 'ld' is 'ilde'.
'm'+'ilde'+'st'='MILDEST'
(Other definitions for mildest that I've seen before include "calmer than all the others" , "Most gentle" .)