Flirt with depression in Yorkshire? Book twice for lodging (6)
I believe the answer is:
dabble
'flirt' is the definition.
(thesaurus)
'depression in yorkshire? book twice for lodging' is the wordplay.
'depression in yorkshire?' becomes 'dale' (as in the Yorkshire Dales).
'book' becomes 'b'.
'twice' shows that letters should be duplicated.
'for lodging' is an insertion indicator (inserted letters lodge within others).
'b' duplicated is 'bb'.
'dale' enclosing 'bb' is 'DABBLE'.
'with' acts as a link.
(Other definitions for dabble that I've seen before include "Engage in dilettante style" , "Wet by splashing or work casually" , "Study or work at casually, not seriously" , "Work (at) frivolously" , "Splash with the hands - work superficially" .)