Should we have connected? (We did)

[GhotiO |fɪʃ|]

This is from Hideo Kojima's trailer for Death Stranding 2. At some point during the trailer, there's a line (link) asking, "Should we have connected?". The problem I have with this is that according to what I've learned "You should have done it" implies that you didn't do it, while "You shouldn't have done it" implies that you did. But in the first chapter (Death Stranding 1), they did "connect" whatever they mean by that. So these two facts kind of contradict each other.

I would've understood the line if they hadn't connected, but they did. So my only understanding now is that "should have + a past participle" could also mean that it was done but now we're asking if the decision was correct. Like here:

A: I told my father what had happened like my girlfriend advised me to. Now he's really mad at me.
B: He'll soon forget everything and it'll all be fine.
A: I don't think so... I really don't. Should I have told him? What do you think? I personally believe it was a very stupid decision.

Is my understanding correct?

 

[Tarheel]

"Should I have told him?" indicates that you doubt that your decision to do so was right. In other words, you are thinking that maybe you shouldn't have done it

 

[GhotiO |fɪʃ|]

"Should I have told him?" indicates that you doubt that your decision to do so was right. In other words, you are thinking that maybe you shouldn't have done it

Thanks! Does this also work if it wasn't done? Like here:

A: I didn't tell my father what had happened like my girlfriend advised me to. Now he's found it out by himself and he's really mad at me (for not telling him).
B: He'll soon forget everything and it'll all be fine.
A: I don't think so... I really don't. Should I have told him? What do you think? I personally believe it was a very stupid decision (not to tell him).

 

[Tarheel]

"Should I have told him?" here means that you didn't, but you that was possibly the wrong decision.

 

[teechar]

but you __________ that was possibly the wrong decision.

I suspect that @Tarheel meant to write something like "suspect" or "think" in that blank.

 

[Tarheel]

I suspect that @Tarheel meant to write something like "suspect" or "think" in that blank.

Yes. Somebody goofed.

 

[GhotiO |fɪʃ|]

So, the affirmative question works in both cases: when you didn't do it and when you did, questioning the decision (to do or not to do) in both?
That's very interesting...

• (1. I did it. Should I have done it?)

A: I told my father what had happened like my girlfriend advised me to. Now he's really mad at me.
B: He'll soon forget everything and it'll all be fine.
A: I don't think so... I really don't. Should I have told him? What do you think? I personally believe it was a very stupid decision (to tell him).

• (2. I didn't do it. Should I have done it?)

A: I didn't tell my father what had happened like my girlfriend advised me to. Now he's found it out by himself and he's really mad at me (for not telling him).
B: He'll soon forget everything and it'll all be fine.
A: I don't think so... I really don't. Should I have told him? What do you think? I personally believe it was a very stupid decision (not to tell him).

 

[5jj]

• (1. I did it. Should I have done it?)

A: I told my father what had happened like my girlfriend advised me to. Now he's really mad at me.
B: He'll soon forget everything and it'll all be fine.
A: I don't think so... I really don't. Should I have told him? What do you think? I personally believe it was a very stupid decision (to tell him).

I'd prefer Should I not have told him?

 

[GhotiO |fɪʃ|]

I'd prefer Should I not have told him.

Thanks for saying this! I needed to know it because it raises two questions for me.

Is the position of 'not' important here? In other words, would
"Shouldn't I have told him?" work as well as yours
"Should I not have told him?"? (in that situation where A did tell his father)

And this is why I was a little puzzled by the line from the Death Stranding 2 Trailer (link), asking "Should we have connected?" and started this thread #1.
Because, knowing the story, in the first project they did "connect" whatever they mean by that. So do you think that
"Should we not have connected?" would sound better to you compared to theirs:
"Should we have connected?"?

Thanks!

 

[5jj]

Is the position of 'not' important here? In other words, would
"Shouldn't I have told him?" work as well as yours
"Should I not have told him?"? (in that situation where A did tell his father)

no. it does not work as well.

So do you think that
"Should we not have connected?" would sound better to you compared to theirs:
"Should we have connected?"?

I do.