Was that a double entendre or not? If not, you might make a literal translation to get the meaning across. If so, then a literal translation will not get the message across. Vice versa, if it was not a double entendre but you translate it as one, you may confuse the message and if it was and you translate it as such, then the human connection can be maintained.
That is also the tricky bit where you cross from being proficient in the language (say B1-B2) to fluent (C1-C2), you start knowing these double meanings and nuance and can pick up on them. You can also pick up on them when they weren't intended and make a rejoinder (that may flop or land depending on your own skill).
If you are constantly translating with a machine, you won't really learn the language. You have to step away at some point. AI translations present that in full: a translated text with a removed voice; the voice of AI is all of us and that sounds like none of us.