This might not count as a Shidduch story since my friend and his wife were engaged at the time but it definitely messed up someone else’s proposal.
This friend goes out to a fancy restaurant to eat with his (at the time) kallah and asks for a table for two. The waiter asks him if his name is Dovid to which he responds, “Yes, Why?”, the waiter just winked at him and said, “Don’t worry everything has been taken care of”.
After they were done eating the waiter asked if they were ready for dessert. A minute later the waiter gave her a cake that said “Will you marry me?”.
They all had a good laugh and he was very thankful it didn’t happen on their first date.