Paid companion shows his age when in trouble (6)
I believe the answer is:
geisha
'paid companion' is the definition.
'geisha' can be an answer for 'companion' (I have seen 'female companion' mean 'geisha' so perhaps 'companion' could also mean 'geisha'). I am unsure of the 'paid' bit.
'his age when in trouble' is the wordplay.
'when in trouble' indicates an anagram.
'his'+'age'='hisage'
'hisage' is an anagram of 'GEISHA'.
'shows' acts as a link.
Can you help me to learn more?
(Other definitions for geisha that I've seen before include "girl from the orient" , "A Japanese woman who entertains men" , "One employed to look after men" , "Hostess in a kimono" , "Japanese girl trained to entertain men" .)