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When someone says: Prepare (by wearing nice clothes) for tonight's date. Over and over again, whenever that person sees you, he tells you that, not to annoy, harras, or bully you, but to make sure that you understand how important is your preparation for that special night.

So, we say: He ______ to get prepared for tonight's date.

I thought of:

He "assured me" to get prepared for tonight's date.

And

He "made sure/confirmed" that I get prepared for tonight's date.

But I found that their meanings are reassure which is like the other way around of the word I want.

The text I have that needs that word (and some correction in its construction, I think) is:

I'm not sure of how Nathan would react to my preparations. He ______ that I get prepared for our only and last night.

That sentence is what a girl says about Nathan, her husband, with a neutral tone, after she didn't have the time to get prepared as she was being told.

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    What kind of tone would you like to express? – mathewb Aug 24 '18 at 17:21
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    If Nathan succeeded in his efforts (i.e. - if you were prepared), you could just say He ensured [that] I was prepared for tonight's date. If he failed (you weren't properly prepared), but you still want to convey that he did try hard, you could include an idiomatic little construction: He was at pains to ensure [that] I was properly prepared - but I'm not ready, so I feel I've let him down. – FumbleFingers Aug 24 '18 at 17:58
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    But to be honest I think there's something not quite right about the required meaning here. If Nathan ensured something, that means he made sure it would happen. Which doesn't make much sense in your cited context, where apparently the speaker has made preparations of his own (which Nathan doesn't even know about, so I don't see how we can talk about Nathan making sure of anything, if he doesn't know exactly what's happening). All you can say is that he wanted you to be ready, or he tried hard to make you get ready. – FumbleFingers Aug 24 '18 at 18:09
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    Every time I saw him he would reiterate that I should prepare for tonight's date. – James Aug 24 '18 at 18:24
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    It isn't really clear what you're asking here when you say "over and over". Are you saying that this person is repeatedly telling you to prepare, that he is nagging or pestering or hectoring or hounding you? Or that he is actually undermining your confidence by constantly telling you to be prepared? – Tᴚoɯɐuo Aug 24 '18 at 19:05
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You say the statement is made with a "neutral" tone, by which I take you to mean that there's no criticism of Nathan's behavior here. You write "as she was being told" so it seems you might want a verb like demanded or made clear or expects.

Nathan demanded that I be ready for the date. I'm not sure how he will react when he finds out that I won't be ready.

or

Nathan made it very clear that he wanted me to be ready for the date. I'm not sure how he will react when he finds out that I won't be ready.

or

Nathan said multiple times that he expects me to be ready for the date. I'm not sure how he will react when he finds out that I won't be ready.

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This is a phrasal verb, not a single word, but it sounds like keep on may fit the bill. It can be used in different ways, but a simple definition is: to continue or persist. A couple of options, depending on what you would like to emphasize would be:

I wasn't sure of how Nathan would react to my (lack of) preparations. He had kept on insisting that I get prepared for our last and only night.

or:

... He had kept on about my preparing for our last and only night.

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The word you are looking for is "ensured."

Assure is more passive: telling someone that something will happen without intervention. It's more like a promise.

Ensure is active: making something happen through some enforcing action, such as reminders to prevent someone from forgetting.

I'm not sure of how Nathan would react to my preparations. He ensured that I get prepared for our only and last night.

  • How would you say that ensure differs from made sure, other than word count? – mathewb Aug 24 '18 at 17:24
  • Nothing really, other than the present tense conjugation ensure is equivalent to make sure, while past tense ensured is equivalent to made sure. – Duncan Aug 24 '18 at 17:27
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    @matthewb I would say that "make sure" is less formal and more colloquial than "ensure" is, as well. – Sparksbet Aug 24 '18 at 18:06
  • Despite my having suggested ensure in a comment, it seems pretty obvious from OP's subsequent comments that Nathan failed to ensure his desired outcome, so it can't be the right answer. – FumbleFingers Aug 25 '18 at 17:24

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