” “Can you give me the name of a friend of her father and a different friend of her mother I can speak to about her?
” “What are the circumstances that led to his parents’ divorce?
the polka dots where they get to express their taste? Discuss yeshiva's, seminaries, free will, how lucky we are to be religious, and the weather.
“Do you know if anyone in his family is taking medications and what those medications are for?
The first quality that comes to mind from the Torah is good Midos.
Avraham did not want Yitzchok to marry the daughters of Canaan (Breishis 24:3 and Kli Yakar there) since he did not want Yitzchok to learn from their bad Midos.
And yet it seems to me that the increasing level of investigation, and some of the latest practices surrounding shidduch dating, are not only failing to yield greater effectiveness or the desired results, but they are compounding some of the existing challenges in the system and are contributing to an inappropriate tone to dating.