I ask myself why, oh why

from Wyclef Jean – Gone Til November Lyrics on Rap Genius

Meaning

He asks himself why because she knows that he has to make a run because he can’t work a regular job and she should understand that when he gets back they’ll be financially stable.

He wonders why she cries, because she knows the nature of his work. Its like how dudes pursue strippers and then wonder why they do what they do AFTER they start dating them.

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