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This question already has an answer here:

I understand it's grammatically correct to use apostrophe s for the plural of letters.

Dot your i's and cross your t's.

But not for proper nouns that end with s.

Here come the Jones's Joneses.

What would the plural of the name Jess be?

Jesses?

Which is also the plural of Jesse. So...

Both Jesses are dating both Jesses. Wait what?

English is just silly.

I understand Jess can stand for Jessica and to reduce confusion we could use Jessicas. However not all Jess..es (lol) are birthnamed Jessica.

And if that wasn't bad enough, we can give the plurals possession...

Both Jesses's cats are playing with the Jesses's dogs.

Now answer this, do the Jesses own cats or dogs? Oh English, you.

If Jesses is the correct plural for Jess, how can English avoid confusion with the plural for Jesse?

marked as duplicate by Mark Hubbard, tchrist, jimm101, Roaring Fish, Nathaniel Feb 9 '16 at 22:49

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    Related question, Family name pluralization and closer one which was closed as duplicate, How to pluralize a last name like Thomas. – user140086 Feb 5 '16 at 14:12
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    Surely in the last example if there are plural possessive names then the apostrophe should not have a following 's'? ... and that would distinguish them from the singular possessive case. – Charon Feb 5 '16 at 14:19
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    Your last example Both Jesses's cats are playing with the Jesses's dogs is simply wrong. As this NGram shows, if the relevant noun already ends with two separate s sounds, and you need to add another for the Saxon genitive (which wouldn't normally be pronounced anyway), you only write the apostrophe, not the extra s. – FumbleFingers Feb 5 '16 at 14:25
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    English and all other languages avoid confusion by being spoken in context and not by being subject to amateurish mocking. Still, even in context rich situations ambiguity cannot be avoided or it might even be intended. What is the beauty of language to one is the morass to another. Perhaps it depends on the person. – GoDucks Feb 5 '16 at 15:43
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    @GoDucks You've just (independently) summarised my answer. :) – Lawrence Feb 5 '16 at 15:44
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According to Jack Lynch, whose book The English Language: A User's Guide is well worth the modest investment for those without the patience to deal with the OED or Fowler,

Many people get spooked by the plurals of proper names, but the rules aren't that different...The only difference between proper and common nouns is that the proper names ending in -y shouldn't change form in the plural: just add an -s. The members of the Percy family are the Percys, not the Percies.

Lynch goes on to warn against pluralizing with punctuation:

Resist the urge to put an apostrophe before the s in a plural, whether in common or proper nouns. The term for this vulgar error is the "greengrocer's apostrophe," from the shopkeepers' habit of advertising their "potato's" and "apple's."

If one has in one's company a multiplicity of persons named Jess, then indeed they are "Jesses". The same spelling would apply in the case of two or more persons yclept "Jesse." They too would be Jesses.

The questioner asserts that "English is silly," which I think is an unkind thing to say about anyone's Mother Tongue. English is sometimes fickle, sometimes illogical, occasionally intractable, but it is capacious, flexible and alive. It tolerates confusion. In figurative and humorous usage, English even thrives on confusion. Comfortable speakers of the language use it as a platform for invention and improvisation.

In the questioner's example, wherein we have a hyperabundance of Jesses of unspoken origin or character, it is likely that one or more of them will have adopted or been given a nickname by their peers: "Spike," "Peach," "Two-Step" or "Four-Eyes." The possibilities of human interaction, mediated by English, are nearly endless!

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The question in your title is already addressed elsewhere, e.g. the site Rathony mentioned in comments (here and there). This answer addresses the ambiguity between the two sets of Jesses.

Words that look the same on the printed page but differ in meaning are called homographs. The inherent ambiguity is part of its nature - they won't be homographs otherwise. They appear in other languages as well: the linked page shows some Chinese examples, and here's another page that purports to show some French examples (though many of them look like English words to me).

Sometimes, very little context is required to disambiguate them. For example, St James St is clearly Saint James Street without the need for further information.

There are occasions where ambiguity is acceptable. You cite the example, "Both Jesses are dating both Jesses." Since both instances of both are not elaborated upon, I'll consider the identity of each reference to "both Jesses" to be prior knowledge. Although we don't know which group of "both Jesses" a particular Jess/Jesse is part of, it doesn't matter here because if one dates the other, then the latter automatically dates the former.

There will also be times when more context is required, such as with your example involving cats and dogs. That's simply the nature of homographs and language. In your dating example, you don't object to the ambiguity of which specific Jess/Jesse dates whom, a matter what is (conceptually, at least) distinct from the issue of homographs - it would still be ambiguous if the Thomases dated the Joneses.

With a rich language like English, ambiguity can sometimes be part of the fun. As the Thomas/Jones example shows, you can have ambiguity even without homographs. The richness of the language also allows other forms of expression when precision is needed and ambiguity is a liability.

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