Chat carelessly during trophy and learn the latest (5,2)
I believe the answer is:
catch up
'learn the latest' is the definition.
I can't tell whether this defines the answer.
'chat carelessly during trophy' is the wordplay.
'carelessly' is an anagram indicator.
'during' means one lot of letters goes inside another.
'trophy' becomes 'cup' (cup is a kind of trophy).
'chat' anagrammed gives 'atch'.
'atch' placed within 'cup' is 'CATCH-UP'.
'and' is the link.
Can you help me to learn more?
(Other definitions for catch up that I've seen before include "Do things which should have been done earlier" , "Backward student must try to do this" , "Sauce" , "Prepare to overtake" , "Lag no longer" .)