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The idiom "to cast a shadow over/on something or someone" means to fill something with grief, dread or any strong emotion. I am going to make up an example with it.

(ex) John used to like math a lot when he was young. However, his repeated failures in the subject made him lose total confidence and have cast a shadow on him ever since.

Am I using the idiom correctly? Thanks a lot.

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    It's usually over, not on. But in your precise context the usage is potentially ambiguous. Most likely you mean that John himself felt "weighed down" by past failures, but it could also be taken to imply that other people view John less favourably because of those failures. – FumbleFingers Jan 15 '17 at 17:05
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Grammatically your ex. is correct, but the idiom feels a little strong and repetitious here. Simplifying it would be better:

John used to like math a lot when he was young. However, his repeated failures in the subject have cast a shadow on his confidence ever since.

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