How do I distinguish simple past and past perfect with “should”?

Question

One type of construction that has always bugged me is the distinction between should (past tense of shall), and its past perfect form. Assume a character, let's call him John:

He lost the poker game. He should have quit while he was ahead, but he didn't listen.

So far, so good. However, moving to past perfect, do I still use the same construction? And if so, are these forms solely distinguished from context?

He had lost the poker game. He should have quit while he was ahead, but he hadn't listened.

This sounds weird to me and I am not sure if it's even correct. My knowledge of English grammar is very intuitive, rather than rule-based, so I was hoping somebody here knew the answer.

Answer 1

Yes, the construction in your second example is correct. There is no other form of 'shall' that could be used in that context, and no other construction using 'should' that would be grammatically correct. I believe that "He should have quit while he was ahead" is an example of the conditional perfect verb form. That part of the sentence doesn't change to be past perfect because it doesn't refer to an event, just to something that could have happened.

Answer 2

The question: How do I distinguish simple past and past progressive with “should”? isn't all that clear to me, because your example doesn't use a progressive tense.

The use of past perfect follows grammar rules with respect to the sequence of events. You may say for example, "He had lost the poker game before he broke up with his girlfriend." The act of losing the game occurred before breaking up and so the first verb is in the past perfect tense.

The sentence, which uses "should have listened" (conditional past) followed by "had not listened" (past perfect) isn't recommended.

"He should have quit while he was ahead, but he didn't listen." The use of simple past here sounds correct. Compare it with: "He wouldn't have lost, if he had listened."