pronouns - Are you comfortable with who(m) he is?

• Are you comfortable with him? (correct)


• 
  

  Are you comfortable with whom he is? (??)

  
  


• 
  

  You're comfortable with whom he is. (??)

  
  


• 
  

  Are you comfortable with who he is? (??)

  
  


• 
  

  You're comfortable with whom? (correct)

  
  

Why does adding he is change the usage of who/whom? I understand that the is is reflective and takes the nominative case, but my brain is not "computing" because I've never seen anything following with ever be nominative...until now.

Please enlighten me.

PS: There are no tags for 'nominative' or 'dative' or likely any of the other cases.

Answer

Whom would be wrong in your example; it should be who. The reason is that a relative pronoun functions as part of the relative clause, not of the main clause. Don't let the question mark fool you: who is a relative pronoun here, not an interrogative one.

Are you comfortable with [the person] who he is?

This shows the structure of your sentence a little better. The person, the hypothetical antecedent of the relative clause who he is, is left out or enclosed in the relative pronoun who. In any case, who is part of the relative clause, not the main clause. That is why we should be looking at its function within the subordinate clause: it is subject (or subject complement) in who he is; therefore we need who, not whom.

It does not matter at all what function the (explicit or implicit) antecedent has in the main clause:

I fear him who gave me life.

I fear him whom I have wronged.

He who gave me life frightens me.

He whom I have wronged frightens me.

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If who/whom is used as an interrogative pronoun, i.e. not introducing a subordinate clause, it is its function in the main clause that matters:

Who are you?

Whom do you see?

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Note that who is now more frequent than whom in any case, and is accepted by most wherever traditionalists would have whom as explained above.