Like hundreds of dates accepted by male singer, American tough guy (6)

I believe the answer is:

badass

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'like hundreds of dates' is the definition.
I don't know anything about this answer so I can't tell whether it can be defined by this definition.

'accepted by male singer american tough guy' is the wordplay.
'accepted by' is an insertion indicator.
'male singer' becomes 'bass' (I've seen this before).
'american tough guy' becomes 'da' (I can't justify this - if you can you should give a lot more credence to this answer).
'bass' placed around 'da' is 'BADASS'.

Can you help me to learn more?

I've seen this clue in The Guardian.

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