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If I have two sentences "You need to start choosing to not do bad things" and "You need to start choosing not to do bad things", is there a difference between the two? If so, what is it?

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    There is no difference in meaning, only in syntax. The not, like all operators with a focus, may go either immediately before its focussed constituent (in this case, before do bad things), or it may go immediately before any constituent that contains the focus (in this case, before to do bad things, since the infinitive clause starting with to contains the focussed verb phrase do bad things. Of course, every time you move the negative up one constituent, you introduce ambiguities because there's more stuff the negative could focus on. So it's not good practice in writing. Commented Sep 17, 2015 at 17:24

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Two sentences are grammatically correct with the exception that the first one is an example of "cleft infinitive/split infinitive"

As we all know SPLIT INFINITIVES are those where adverb/adverbials are placed between 'TO' and 'BARE INFINITIVE' and its propriety has been an issue of contention since nineteenth century. However, presently we accept it as a grammatical form but are reserved about its rampant usage.

Columbia Guide or Oxford dictionaries advise us to avoid Split Infinitive if we can. Our hesitation to split infinitive follows from the false notion that we regard "TO" to cling to the "BARE INFINITIVE" and inseparable.

According to modern grammar, the first example in the post has split infinitive. We are of the view that placing the negative before the marker(choose not to do) or negating the finite verb (He doesn't choose to do) is easy, natural and common construction. We should be on our guards not to use split infinitive unless otherwise so warranted as in:

She decided to gradually reduce her stock of teddy bears.

'Gradually' is placed here at the best possible position.

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While many will tell you that "to not" is just fine and in some cases has a different meaning from "not to", I would not recommend it. My personal reaction to "to not" is quite strong and quite negative. I always look for another way to phrase what I want to say so that I can avoid it. "to never" is equally awful to my ear.

In order not to bother my roommate, I left the apartment.

Not to bother you, but may I have some change?

Stolen from CalifJim here.

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    I'm sorry to hear that you have such a strong allergy to that string, @AboAmmar. I hope you recover soon. Commented Sep 17, 2015 at 19:36
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I don't know how relevant this is in English any more, but I was taught that "it is wrong to ever split an infinitive". In your sentence the infinitive is "to do" so you shouldn't put any words between "to" and "do".

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  • It is not wrong to split an infinitive and is very common in informal English and sometimes necessary in formal English even. Commented Sep 20, 2015 at 9:56
  • According to the wikipedia article for split infinitive, it is the most hotly contested construction in the English language. While it is widely used, there are still many grammarians who oppose its use. Commented Sep 20, 2015 at 15:41

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