Plight of a boyfriend after fine? (8)
I believe the answer is:
affiance
'plight' is the definition.
('affiance' can be a synonym of 'plight')
'a boyfriend after fine?' is the wordplay.
'boyfriend' becomes 'fiance' (I can't justify this - if you can you should give a lot more credence to this answer).
'after' means one lot of letters go next to another.
'fine?' becomes 'f' (abbreviation).
'fiance' put after 'f' is 'ffiance'.
'a'+'ffiance'='AFFIANCE'
'of' is the link.
Can you help me to learn more?
(Other definitions for affiance that I've seen before include "Betroth, become engaged" , "Bond" , "Betroth with face I fan" .)