This sentence from an article strikes me as somewhat unusual. Since the modified antecedent is a point in time, why is "that" the relative pronoun instead of "when"?

I met Jonathan Annicks shortly after the night two years ago that he was shot sitting in his brother’s car outside his home.

Also, can the relative pronoun in this situation be omitted? Namely, can I write a sentence such as:

I met him shortly after the night he was shot.

This sentence reads totally fine to me, but according to several online sources the relative pronoun can be left out only when it is the object of the verb in a defining relative clause, but this sentence doesn't seem to be such a case.

  • I think, here applies definition #7 a, from TFD in which, that is, the night in which he was shot. – Lucian Sava Nov 11 '18 at 16:28
  • It's not uncommon at all. google.com/… From The Grammarian: "That small, nasty exchange had colored his whole trip, and the night that it happened he fantasized about slitting the man's throat." Grammar can do that to you. – Tᴚoɯɐuo Nov 11 '18 at 17:03
  • You can certainly omit the "that": the rule you have is too narrow. It can be omitted except when it is the subject. Eg "the table [that] I put it on". – Colin Fine Nov 11 '18 at 19:01

"that" and "when" are interchangeable in the first sentence. Which night was it? "The night on which he was shot" "The night that he was shot" "The night when he was shot" all work.

As for your second question: In your example, you can leave the pronoun out. The original sentence can't. Why? Because of "two years ago". If you try to leave the pronoun out of the original sentence, you get

"the night two years ago he was shot" which is clearly incorrect. You could rearrange it, however, and make it "the night he was shot, two years ago".

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