Red-headed lady losing heart without confidence (8)
I believe the answer is:
gingerly
'without confidence' is the definition.
I can't judge whether this definition defines the answer.
'red-headed lady losing heart' is the wordplay.
'red-headed' becomes 'ginger' (I can't justify this - if you can you should give a lot more credence to this answer).
'losing heart' says to hollow out the word (remove centre letters).
'lady' with its centre removed is 'ly'.
'ginger'+'ly'='GINGERLY'
Can you help me to learn more?
(Other definitions for gingerly that I've seen before include "With soft steps" , "Cautiously (as if in pain?)" , "With extreme care and delicacy" , "In a careful manner" , "Showing caution" .)