His empty pockets won't succeed with her

[GoodTaste]

Pocket: financial resources:
His empty pockets won't succeed with her.

Source: Random House Learner's Dictionary of American English

I understand "His empty pockets won't succeed with her" as "His empty pockets won't win her as his girlfriend". Am I on the right track？

 

[Skrej]

More or less. It means he won't impress her with his lack of money. Exactly why he's trying to impress her, we don't know for sure. However, romantic interest is probably the most likely reason, yes.