I’m writing this in reply to a Twitter conversation.
When you listen to a video or a CD and don’t understand, how many times should you repeat it or replay it?
As many times as it takes. However, are you taking notes? Can you check words in a dictionary. Can you repeat what the speaker says?
If you can take notes, this helps. You will get hints about conversational topics and maybe even guess how the topic will change.
If you can check words in a dictionary, you can check that you understand correctly.
If you can repeat what the speaker says, you can use your phone to take notes, then make paper notes too.
I hope this helps.