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  1. I can repair your car. Keith and Roger will make a mess of it.

  2. I can repair your car. Keith or Roger will make a mess of it.

  3. I can repair your car. Either Keith or Roger will make a mess of it.

If the idea is: I can repair your car. Keith will make a mess of it. Roger will make a mess of it too.

Which of the sentences should be used?

If there are two options: one being that I will repair the car and the other being that Keith and Roger will try to repair it together then obviously '1' should be used.

But what if we have three options: Either I will repair it; or Keith will try to repair it (and will make a mess of it); or Roger will try to repair it (and will make a mess of it)?

Which one should be used in that context?

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    Forget about the word either for your utterances here. Your third option is syntactically valid, but idiomatically very unlikely. Your first two examples are syntactically / idiomatically fine, and the and / or choice disambiguates between whether there are one or two alternatives (Keith and Roger working together, OR either Keith or Roger working alone).
    – FumbleFingers
    Nov 7, 2022 at 13:27
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    OP, it's worth noting that English is incredibly ambiguous, and, messy. For many formulations, such as your example, there is honestly no good solution. For example, when you are writing dialogue (eg, screenplays, etc) it's often extremely difficult to make things like that really clear, and short. Very often in real life we say the thing that is "wrong", and, hope it is understood.
    – Fattie
    Nov 7, 2022 at 14:34
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    In actual speech, another possible way to express the three options is: "I can repair your car. Keith would make a mess of it. So would Roger."
    – David K
    Nov 8, 2022 at 1:29
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    Casual speech does not conform to rigorous formal logic. Humans use whatever sounds the most sensible to them. For example, if I say "I want Bob or Harry to leave this room", in formal logic that would be an XOR, not an OR.
    – Flater
    Nov 8, 2022 at 5:59

4 Answers 4

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Each of your examples might be spoken by a mechanic working on a movie who has been told, "We need this car to work properly but it has to look dirty and battered." In that context it would mean,

I can repair it, then [either] Keith and/or Roger will make a mess of it.

But to mean what you want it to mean it might be better to use "would" instead of "will"

I can repair your car.

Keith and Roger would make a mess of it.
Keith or Roger would make a mess of it.

And instead of "Either Keith or Roger would...", I would say,

Both Keith and Roger would make a mess of it.

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    In my area (US, east coast) we would use "will" the way the OP means it. I think the subjunctive mood might be dying.
    – user3067860
    Nov 7, 2022 at 16:39
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    in the uk we would use either would or will actually we would say "they'd make a mess of it" or "they'll make a mess of it"
    – WendyG
    Nov 8, 2022 at 17:24
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If Keith and Roger are working independently then you only need 2. the "Either" in 3 is superfluous as we know it can't be both. All 3 are grammatically correct.

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Keith and Roger would make a mess of it.

This generally means Keith and Roger are working together, and they would make a mess of it.

Either Keith or Roger would make a mess of it.

Either-or would generally mean one of them would make a mess of it and the other wouldn't (and this doesn't specify which). But that is a strange thing to say, so without further context, most people would probably interpret this as: Keith would make a mess of it and Roger would make a mess of it.

Keith or Roger would make a mess of it.

This generally means either (a) one of them would make a mess of it and the other wouldn't or (b) Keith would make a mess of it and Roger would make a mess of it.

Both Keith and Roger would make a mess of it.

This generally means Keith would make a mess of it and Roger would make a mess of it. So this is probably the best one to go with for what you want to say.

Either of Keith or Roger would make a mess of it.

This is a slightly unusual phrasing, but it would also mean Keith would make a mess of it and Roger would make a mess of it.

"Either" roughly means "one of them", whereas "either of" means "it doesn't matter which one".

The more natural version of the above would use "them" to refer to Keith and Roger, e.g.:

Keith or Roger? Either of them would make a mess of it.

"or" translates to "and" in some examples above, because it's basically saying pick one of two (which is "or"), and the one you picked would make a mess of it (which means they would both make a mess of it, which is "and").

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Each of the three options that you have provided (be it a tutorial exercise or whatever) are a little ambiguous as they stand which leaves them open to be mis-interpreted... and hence your asking of the question as to which it is clearest and best way of getting across what you actually mean.

I would say that, in natural speech, it is better to be more explicit and add some extra words to make it very clear what you intend to say, and avoid any mis-understanding, for example:

It is best that I repair your car because Keith or Roger will make a mess of it.

or, using would (as Old Brixtonian suggests), and expanding the sentence further:

I think that it is better that I repair your car because Keith or Roger would make a [right old] mess of it.

These two examples leave no doubt that what you mean is that you are better placed, or equipped, to make the repair, than either Keith or Roger working seperately.

However, if the examples that you provide are part of a multiple choice exercise, and given the three options to the outcome (as stated in the latter part of your question) then I would state the option 2 is the most natural and closest to what you mean to say:

I can repair your car. Keith or Roger will make a mess of it.

Or, keeping the same "format", it would be better still to say

I can repair your car [for you]. Keith or Roger will/would [just] make a mess of it.

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