Something after work? Go with gentleman (9)
I believe the answer is:
weeknight
'something after work?' is the definition.
I can't judge whether this defines the answer.
'go with gentleman' is the wordplay.
'go' becomes 'wee' (both can mean to urinate).
'with' means one lot of letters go next to another.
'gentleman' becomes 'knight' (I can't justify this - if you can you should give a lot more credence to this answer).
'wee'+'knight'='WEEKNIGHT'
Can you help me to learn more?
(Other definitions for weeknight that I've seen before include "time to sleep after work" , "Bit of time" , "evening between Monday and Friday" , "appears between working days" , "Friday even, for example" .)