How crazy can “and” be?

Question

After seeing completely insane examples of "and" usage in this question , I realized that I have no clue how to use the word "and" grammatically:

How far does the insanity go? Are the following grammatical?

1. John is, and Sally hates, cooking.
2. John has once ineptly, and Sally hates, cooked meat.
3. Sally hates, and Michael said that John has ineptly, boiled vegetables.
4. Sally, at the bakery, bought, and the makeup on her nose, cakes.

If 2 is grammatical, what does Sally hate exactly? If 3 is grammatical, does Sally hate boiled vegetables, or boiling vegetables? If 4 is grammatical, I'm going to cry.

This question is inspired by trying to incorporate "and" into a mechanical parsing of English, which, surprisingly, is a lot tougher than anything else.

Answer 1

All of your examples, while not exactly nonsensical, are highly unusual. They all include words that are forced to display multiple incompatible meanings:

1. The verb form is cooking, versus the noun cooking

2. The verb form has cooked with the object meat, versus the noun phrase cooked meat

3. The adjective boiled, versus the verb form has boiled

4. The verb bought with the object cakes, versus the verb form cakes

The question you linked asks about who serving as both object and subject; this is allowable because the sense of the word who is preserved. Though it serves multiple grammatical functions in the sentence, it displays only one meaning.

Though all of your examples can be parsed, they are not natural constructions in any dialect of English, and no native speaker would regularly produce them. The problem is that this is a question not of syntax but of semantics. A parser that recognises statements such as these must allow terms not only to have multiple simultaneous meanings, but also to overlap one another.

Answer 2

At least one word in each example is shifting both in meaning and in part of speech. An author may employ this shift for stylistic effect, but the more complex the shifts, the more difficult it is to parse, and the less effective the play on words becomes.

I would be hard pressed to find someone who used such phrasing in conversational English. You will see simple examples in writing when authors are striving for parallelism or perhaps humor. For example, Alexander Pope writes in The Rape of the Lock:

There stands a structure of majestic frame,

Which from the neighb'ring Hampton takes its name. ...

Here thou, great Anna! whom three realms obey,

Dost sometimes counsel take— and sometimes tea.

To take counsel and to take tea are very different activities despite sharing the word take, but the meaning of take (to accept or consume) and the part of speech (verb) do not change. There is little chance of confusion, and the turn of phrase is deemed clever.

None of your examples, however, will be mistaken for the writings of Alexander Pope.

The first example may pass muster because it is short, with no modifiers, and while cooking is the main verb in the first part and the gerund object of hates in the second, it still refers to the same activity.

There is too much going on in the other examples to make any sense.

John had once ineptly, and Sally hates, cooked meat.

In the first part, had cooked is the verb with meat as its object, whereas in the second, hates is the verb and cooked meat the object. Perhaps some would read had as the first verb with cooked meat likewise its object, except that ineptly would not make sense. The third example has the identical ambiguity with regards to boiled vegetables, but simply adding Michael has adds enough complexity to make it difficult to parse. The fourth example, in which cakes is alternatively a verb and a noun and an already unnatural word order is interrupted with multiple commas, is quite unreadable.