Complying with old boy looking on (7)
I believe the answer is:
obeying
'complying' is the definition.
The answer and definition can be both to do with social activities as well as being present participle verbs.
Perhaps you can see an association between them that I can't see?
'with old boy looking on' is the wordplay.
'with' means one lot of letters go next to another.
'old' becomes 'o' (common abbreviation eg in OE for Old English).
'boy' becomes 'b' (abbreviation used in schools).
'looking' becomes 'eying' (I've seen this before).
'on' is a charade indicator (letters next to each other).
'o' next to 'b' is 'ob'.
'ob'+'eying'='OBEYING'
Can you help me to learn more?
(Other definitions for obeying that I've seen before include "Following orders" , "Carrying out orders" .)