[Grammar] After an awkward silence, Kelly continued trying to break

[Nikitus]

Hello.

Are the following sentences grammatically correct?

"After an awkward silence, Kelly continued trying to break the ice with Tim, whom he had not seen in person for 20 years, and with which his relationship was limited to say "Hello" to each other when they met in the corridors of the high school."

Thanks.

 

[teechar]

Tim, whom he had not seen

The "whom" refers to Tim, and the "he" refers to Kelly. Is Kelly male or female?

and with which his relationship was limited to saying "hello" to each other when they met in the corridors of the high school."

Do you see the mistake there?

 

[Nikitus]

Dear teechar: First of all, thanks for your answer.

Kelly is a female, so

Kelly continued trying to break the ice with Tim, whom she had not seen in person for 20 years.


and with which his relationship was limited to saying "hello" to each other when they met in the corridors of the high school."

I believe using the pronoun which is a mistake in this case.

and with their his relationship was limited to saying "hello" to each other when they met in the corridors of the high school."

Are the changes correct?

Thanks.

 

[teechar]

Kelly is a female, so

Kelly continued trying to break the ice with Tim, whom she had not seen in person for 20 years.

That's right.

and with which his relationship was limited to saying "hello" to each other when they met in the corridors of the high school."

I believe using the pronoun "which" is a mistake in this case.

Yes, "which" is wrong. The reference is still to Tim. Try again.

and with their his relationship was limited to saying "hello" to each other when they met in the corridors of the high school."

That's incorrect.

 

[Nikitus]

Dear teechar: Once again, thanks for your answer.


"Kelly continued trying to break the ice with Tim, whom she had not seen in person for 20 years. In the past, the relationshiop between them was limited to saying "hello" to each other when they met in the corridors of the high school."

Is that grammatically correct?

Thanks!

 

[teechar]

That's okay. You could have also said "... with Tim, whom he had not seen in person for 20 years, and with whom his relationship was, etc."