This happened to a former student of mine (I heard it from him)-
He’s driving her back after a great second date (the first one went great as well) when she asks if she can ask him some questions. He agrees.
“So, thinking about your upbringing, can you relate to me a decision that your parents made that you agreed with and a decision that they made that you don’t agree with?”
He was totally caught off guard and was speechless.
She told him that if he didn’t have an answer right away she’ll go on to the next question and he can think about it and give her an answer on the next date.
“So, thinking about your current chavrusa and a former chavrusa, can you tell me something that you like better about your current chavrusa and something you like better about your former chavrusa?”
Again he’s caught off guard and is speechless. She again offers to go on while courteously allowing him to bring an answer to that question as well to the next date.
Without looking up from the road he asked her if she’s reading these questions off a paper or something, but she said that she forgot the list of questions at home so she’s going by her memory.
By the time he got to her house he hadn’t been able to answer a single question of hers but she gracefully allowed him to answer all her questions on a subsequent date.
Unfortunately for her- there was none.
A few weeks later I noticed that he wasn’t by the Mincha that we usually went to and his brother told me that he was on a date.
I sent him a text- “So, thinking about the girl you’re currently dating and a previous girl you dated, tell me something that you like better about this girl and something that you liked better about the other girl?”
He texted back that they both found it hilarious. (They eventually got married.)