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When someone says something like "He will have his work cut out for him when he gets there" is it somehow implicit that the person who is saying it doesn't believe that the person he is talking about will be able to do the task, that he will fail, give up or something like that?

Also, can this expression be used figuratively, and even with a bit of sarcasm, like in the phrase:

Are you sure that he's gonna marry her? Well, he will definitely have his work cut out for him.

Finally, is it possible to use "is gonna" instead of "will have", for example: "He is gonna have his work cut off for him, no doubt about it".

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    You see gonna in sub-titles, but it is not good in writing unless you are writing dialogue. the work cut out for you comes from cutting the pieces in sewing which then have to be sewn up, that's the work.
    – Lambie
    Jun 11 '19 at 20:49
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    There is no implicit suggestion of failure in that phrase; more of a challenge. Jun 11 '19 at 20:50
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There is no implicit suggestion that the person will fail, only that it will be difficult. Instead it suggests that success is possible if the person works hard.

It is possible to use "going to" for the future tense instead of "will".

The example with the marriage is odd. It seems to suggest that his bride will be difficult, but the context seems odd. It is not a very nice thing to say about her, and makes the speaker sound rather unpleasant.

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    Thanks a lot for your help, James. Just to make sure I can understand it correctly, the phrase about the marriage is odd because the expression in question is not commonly used figuratively, or because it's not something very nice to say about someone. Thanks again.
    – Itamar
    Jun 11 '19 at 21:30
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    @Itamar IMO in the quoted marriage context it is odd, because who ever is saying it is suggesting that dealing with the bride with be a tough job. That is a slightly unusual thing to say about a prospective marriage, but it is perfectly possible. The expression is often, indeed mostly, used figuratively, but not so often about a marriage. Jun 11 '19 at 22:04
  • Thank you, David, for making that clear for me. Thank you all, you guys, for helping me with this question.
    – Itamar
    Jun 11 '19 at 22:21

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