Roland endlessly bored by dame's male friend (3,4)
I believe the answer is:
old bean
'male friend' is the definition.
'old bean' can be an answer for 'friend' (I've seen this before). I'm unsure of the 'male' bit.
'roland endlessly bored by dame's' is the wordplay.
'endlessly' means to look at the middle letters (the ends of the words are removed).
'bored by' indicates putting letters inside (to bore something can mean to drill into it).
'dame' becomes 'DBE' (Dame of the British Empire).
The central letters of 'roland' are 'olan'.
'olan' placed around 'dbe' is 'OLD BEAN'.
Can you help me to learn more?
(Other definitions for old bean that I've seen before include "Familiar way to address" , "dated friend" , "Good friend" , "dear fellow" , "Affectionate form of address to a man" .)