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When using the word "self" like this:

"My dumb self tripped over the rock,"

would "dumb" and "self" be hyphenated?

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No, you would not hyphenate them, as "dumb" is simply an adjective clarifying the noun "self", no different than any other adjective-noun pair (i.e. "a tall mountain" or "a long walk").

The time to hyphenate two words is actually when you are creating a compound adjective by combining two or more words into an adjective. For example, in the phrase I wrote above ("adjective-noun pair"), the words "adjective" and "noun" are combined to create a compound adjective that clarifies the noun "pair". So using your sentence, you would use a hyphen if you wrote something like "my stone-dumb self tripped over the rock".

Hope that helps!

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No. You are simply the subject and object of a prepositional phrase, and dumb is an adjective describing the object (self). It is entirely equivalent to:

My expensive cell-phone exploded in my briefcase.

I've hyphenated cell phone for clarity.

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