Road worker to laze around with one old man and boy (unknown) (8,4)
I believe the answer is:
lollipop lady
'road worker to laze around' is the definition.
I don't know anything about this answer so I cannot tell whether it can be defined by this definition.
'one old man and boy unknown' is the wordplay.
'one old man' becomes 'lollipop' (I can't justify this - if you can you should give a lot more credence to this answer).
'and' says to put letters next to each other.
'boy' becomes 'lad' (informal term for boy).
'unknown' becomes 'y' (algebra).
'lollipop'+'lad'+'y'='LOLLIPOP LADY'
'with' acts as a link.
Can you help me to learn more?
(Other definitions for lollipop lady that I've seen before include "Woman seeing children safely across the road" , "Female crossing attendant" , "helps schoolchildren" , "Road crossing attendant" .)