You can use either "reenter" or "re-enter." If you follow a style guide, check to see what it recommends. Otherwise, use what you prefer and be consistent.
Last week, our editor at Quick and Dirty Tips had a question about hyphens as she was working on a post about the anxiety people may feel when they re-enter society after the quarantine.
She found that online dictionaries list both versions as correct—“re-enter” with a hyphen and “reenter” without a hyphen—and she wanted to know which one I prefer.
Since I thought some of you might be facing the same question as you’re writing these days, I’ll share my thoughts.
Even though the trend these days is to use fewer hyphens, I like the hyphenated version when you encounter a double vowel, like those two E’s back-to-back in “reenter,” because I find those words easier to read with a hyphen.
And this is a case where you should definitely check your style guide if you are required to follow one. For example, you should leave out the hyphen if you follow AP style or Chicago style. It isn’t often that I disagree with both of these style guides, but in this case, I do.
So although AP style and Chicago style are “reenter” without a hyphen, Quick and Dirty Tips house style is now “re-enter” with a hyphen.
[Note 6/29/2020: A reader named Alfred charmingly suggested that I forgot an option: “reënter.”]
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