This isn’t quiet a shidduch story but it’s cute.
To preface, chabad have a minhag that when a guy and girl decide to get engaged they go to get resting place of the last chabad Rebbe zatzal before announcing the engagement, I think they go, say some tehillim by the kever, then announce the engagement
There is a chabad couple in kiruv, living out in the middle of nowhere, by a Shabbos meal their young daughter says a dvar torah and in it mentions the word cemetery. One of the guests curiously asks her “do you know what a cemetery is?”, the little girl says “yes, it’s a place where people who passed away are buried, and where people go to get engaged”
I personally know this couple although I did not hear this story from them