This is a slightly wacky sentence. It’s not wrong - it does make sense and communicates the idea, it just forces you to do a bit of work to straighten it out in your head.
I think the biggest issue is the way they unnecessarily used present continuous tense with “be starting to get”.
It’s convoluted and adds syllables. You could eliminate the “be” and “to” entirely and change it to “start getting”. That starts with an active verb which feels stronger and more natural.
So then it would be:
“This can’t possibly be the same 9pm I used to start getting ready for a night out at”.
That preserves the flow & punch of the delivery but shortens & simplifies it a lot without losing anything imo.
Also ending a sentence with a preposition can be awkward. You read “at” and you need to refer it back to 9pm near the start of the sentence. Plus it comes after another preposition, which itself is not acting as a preposition but as part of the nouned phrase “night out”, so you end up with “out at”. Again, not wrong, but it can be awkward. I think using “at which” can move it closer to the noun it’s referring to but it’s not necessarily better that way.
Make that change and it’s, “This can’t possibly be the same 9pm at which I used to start getting ready for a night out”.
It’s a little easier to parse, but honestly I think it loses something, because it doesn’t have a casual delivery. “At which” is evidence that the sentence was very deliberately constructed. It adds a syllable and loses some punch. I’d stick with just the first change personally.
Yeah, that scans for me. It breaks up “getting ready…for a night out”, but I think it works.
I think honestly it’s just a reality that, if brevity is the soul of wit, then a punchy sentence needs to be compact and that means you need to get a bit funky with the grammar, so maybe the audience has to do a little work.
Maybe also “at which” is fine too, and I was just overthinking it.
One thing I won’t bend on is that “to be starting to get ready” is objectively worse in every respect and is the main thing that throws people about the sentence.
This is a slightly wacky sentence. It’s not wrong - it does make sense and communicates the idea, it just forces you to do a bit of work to straighten it out in your head.
I think the biggest issue is the way they unnecessarily used present continuous tense with “be starting to get”.
It’s convoluted and adds syllables. You could eliminate the “be” and “to” entirely and change it to “start getting”. That starts with an active verb which feels stronger and more natural.
So then it would be:
“This can’t possibly be the same 9pm I used to start getting ready for a night out at”.
That preserves the flow & punch of the delivery but shortens & simplifies it a lot without losing anything imo.
Also ending a sentence with a preposition can be awkward. You read “at” and you need to refer it back to 9pm near the start of the sentence. Plus it comes after another preposition, which itself is not acting as a preposition but as part of the nouned phrase “night out”, so you end up with “out at”. Again, not wrong, but it can be awkward. I think using “at which” can move it closer to the noun it’s referring to but it’s not necessarily better that way.
Make that change and it’s, “This can’t possibly be the same 9pm at which I used to start getting ready for a night out”.
It’s a little easier to parse, but honestly I think it loses something, because it doesn’t have a casual delivery. “At which” is evidence that the sentence was very deliberately constructed. It adds a syllable and loses some punch. I’d stick with just the first change personally.
I think I was able to bring the ‘at’ closer to the time, but I’m not sure it’s correct:
‘This can’t possibly be the same 9pm I used to start getting ready at for a night out’
I’m tempted to remove the ‘used to’ and just put it in simple past for brevity, but that would hold back half the punch.
This is one of my favorite types of discourse. Polishing jokes and grammar in the gravitas it deserves.
Yeah, that scans for me. It breaks up “getting ready…for a night out”, but I think it works.
I think honestly it’s just a reality that, if brevity is the soul of wit, then a punchy sentence needs to be compact and that means you need to get a bit funky with the grammar, so maybe the audience has to do a little work.
Maybe also “at which” is fine too, and I was just overthinking it.
One thing I won’t bend on is that “to be starting to get ready” is objectively worse in every respect and is the main thing that throws people about the sentence.