Gloomy, we ask person to include option upfront (9)
I believe the answer is:
woebegone
'gloomy' is the definition.
(thesaurus)
'ask person to include option upfront' is the wordplay.
'ask' becomes 'beg' (begging is a kind of asking).
'person' becomes 'one' ('one' can mean an unspecified person).
'to include option' becomes 'woe' (I am not sure about this - if you are sure you should believe this answer much more).
'upfront' says to put letters next to each other (some letters go in front of others).
'beg'+'one'='begone'
'begone' put after 'woe' is 'WOEBEGONE'.
'we' is the link.
This may not be correct. It may be part of another bit of the clue.
Can you help me to learn more?
(Other definitions for woebegone that I've seen before include "Sad, miserable" , "Sorry" , "dismal look" , "Dismal-looking" , "forlorn state" .)