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Example sentence:

She cried on her boyfriend's chest. It wasn't until she had dried (out) and drenched his shirt, that she began explaining.

Does it make a difference if you include the out in situations like these? Why or why not?

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OP's text is a very clumsy usage in the exact context, because it confuses two different usages...

1: To cry oneself out (as discussed on wordreference.com)
to cry until you feel you have no more tears to shed, either because you've recovered to some degree or you've given up.
(note that this idiomatic usage always includes a reflexive pronoun - oneself, herself, etc.)

2: To dry something out (thefreedictionary.com)
to make or become dry


In practice, it's probably more accurate to classify OP's text as invalid, rather than simply clumsy, because native speakers never use to dry or to dry out for sense #1 above. So it should be...

It wasn't until she had cried herself out and drenched his shirt...

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The out modifier indicates that an action is completed, for example you can say that a product is sold out if all stock of it has been sold.

The milk had sold out long before I got to the shop.

dried out means that something is completely dry, and no further water is left.

Its usage in this context is unusual, and maybe is intended to suggest that she could cry no more because there was nothing left in her tear ducts. I would expect to see until she was cried out. This usage appears in the Alison Moyet song "All Cried out".

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