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I couldn't seem to get clarity from the NYT archive on this.

Here's my situation:

a former coworker who they play golf with and feel comfortable directly texting or calling anytime with questions

See here:

A century ago, it was standard to write any time as two words in all contexts. But it’s now perfectly acceptable to write anytime as one word when you’re using it as an adverb. However, some readers still consider it a casualism, so you may want to stick to the two-word version for extremely formal writing.

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Bryan Garner (Modern English Usage, 4th Ed., 2016) ranks anytime (adverb = at any time; whenever) at Level 5 ("fully accepted") in his Language Change Index, commenting as follows: "Some writers consider this term a casualism, but it is highly convenient and has—for whatever reason—gained more widespread acceptance than anymore (in positive contexts) and *anyplace" (p. 58).

Last edited by David, Moderator

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