Gets uncool boyfriends? (5)
I believe the answer is:
dates
'boyfriends?' is the definition.
The answer and definition can be both people as well as being plural nouns.
Maybe there's an association between them I don't understand?
I cannot understand how the rest of the clue works.
Can you help me to learn more?
(Other definitions for dates that I've seen before include "Dried fruit" , "Meetings arranged in advance" , "Days in calendar" , "Fruits for social engagements" , "Trysts" .)