Be sure never to keep/ to never keep your desk unclean.

Question

1. Be sure never to keep your desk unclean.2. Be sure to never keep your desk clean. Which is grammatical?

GPY · Accepted Answer

Are you sure you typed the question exactly as you intended?

Michelle Cha · Answer

Sorry for the mistake. My actual questions are

1. Be sure never to keep your desk unclean.

2. Be sure to never keep your desk unclean.

Which is grammatical?

GPY · Answer

These both sound convoluted and odd. I can't imagine either being used. You would say "Be sure to always keep your desk clean/tidy".

In a more natural context, I would accept both "be sure never to + verb" and "be sure to never + verb". The former is probably more traditionally correct.

CalifJim · Answer

Michelle Cha 1. Be sure never to keep your desk unclean. 2. Be sure to never keep your desk clean. Which is grammatical?

The advice has long been not to split an infinitive (insert a word between 'to' and the verb), and I still follow that advice whenever possible. Therefore, I much prefer never to keep over to never keep. However, the split infinitive is now used by many writers, so it is not looked upon so negatively as it used to be.

There are other problems with your sentence that should be mentioned.

1. It is not usual to use 'unclean' as the opposite of 'clean'. A floor may be clean or dirty. A desk may be tidy/clean or untidy/messy.

2. To keep something in a given condition (clean, tidy) requires active effort. It takes no active effort for something to become dirty or messy, so keep is the wrong verb. We let things get dirty or messy. It takes no effort. When we let our desks get messy, it is because we have failed to keep them clean.

3. You don't have to use an infinitive after "be sure", but I think you already knew that.

I suggest (AmE):

Be sure that you never let your desk get messy.

CJ

Be sure never to keep/ to never keep your desk unclean.

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