What should I actually ask about when checking a shidduch?ask your rav
Ask only about what matters for a life together: character and everyday yiras shamayim, not school grades or minor habits -- compassion, patience, whether someone tends to give or to demand, anger and pride, relationships with family and friends, behavior in a dorm, whether there's a rav or mentor, goals in learning and earning a living -- and for each point, ask for a concrete example. The point of checking is not 'is this a good person' but whether he or she is right for you; after a reasonable check, what's left is tefillah.
He suggests asking trustworthy people only about what's directly relevant to the shidduch itself. "Only ask about what's directly connected to the shidduch itself." Two versions tie this to readiness to give to a spouse, to compromise, and to work on one's character, rather than trying to predict the whole future. When a suggestion is suitable and the girl is interested, he warns against dragging things out over something unimportant.
They suggest questions about compassion, patience, and other traits important to you, relationships with close family, temperament, and long-term goals in learning and earning a living. "Does this match up with the most important traits on your list?" Family difficulties don't always count against a candidate; they advise discussing troubling circumstances with a rav.
In a letter he points to a lack of information about a girl's real, everyday attitude toward Yiddishkeit and mitzvos. This matters for the future home: "The running of the home, and to a great extent the husband's conduct too, depend on the attitude of the woman of the house." The question concerns actual behavior, not one general label.
He suggests looking at character and yiras shamayim, not academic achievement. "The focus should be on her middos and yiras shamayim, not her scholastic ability." He also prefers a stronger yiras shamayim over the father's scholarship as the advantage of one family over another.
A father who asked only about a young man's scholarship heard from him that he was looking for a prestigious son-in-law for himself, rather than a good husband for his daughter. One needs to find out how he treats others in the dormitory and dining hall.
“His great sharpness in learning Keszos won't do his wife much good!”
She suggests gathering opinions and meeting people from the candidate's life -- family, friends, a rav, and an employer. After the necessary checking, there's still the limit of human knowledge: "After that, only tefillah can help." This combines effort with an acknowledgment of its limits.
Instead of minor everyday details, he advises finding out about upbringing, honesty, generosity, sensitivity, and attitude toward other people's needs. He especially singles out anger and pride: "These traits can destroy shalom bayis." The questions should reveal whether a person tends to give or to demand, and whether he's able to consider someone else.
He acknowledges the general topics of health, family, and upbringing, but beyond that doesn't propose imposing the same list of qualities on everyone. "There won't be an objective checklist: personal inclinations and preferences matter." A person needs to understand who he personally would be happy with.
She defines the purpose of reference checks through personal compatibility. "You're finding out not whether this is a good person, but whether he's right for you." The order in which the two sides make their calls can differ.
She advises starting with a simple request to describe the person -- while keeping in mind the frame of reference the other person is answering from. From there, the questions follow: how would you describe his character; what stands out about him; does he show maturity and depth -- with an example; does he notice other people's needs -- with an example; is he close with his family; is he well liked and well received by his peers; what's his strongest trait; is he materialistic, and in what way exactly; is he "geshikt," meaning capable and competent, and how; do you see him as emotionally stable. Asking for an example here isn't a formality -- it's exactly what separates a real answer from general praise.
“Do you consider him an emotionally stable person?”
About a young man, she advises asking: how does he relate to his mentors and to his friends; if you're speaking with a roommate -- is he considerate of him, and does he keep his things in order; is he serious about learning, and how much longer does he see himself learning full-time; is he conscientious about coming to davening and to his learning partner on time; does he have a rav he consults and follows; is he learning for the right reasons; if he's not in the beis medrash all day, does he have his own set learning schedule; what do you think matters to him in a girl, and where do you see him in ten years. About a girl -- describe her religiously and in outlook; does she genuinely want a husband who learns, and for how long; does she value a husband who puts learning above leisure; does she have a mentor she turns to for advice; were there role models that shaped this desire; how does she present herself, and does her tznius and style of dress match her outlook; how does she spend her free time; is her personality gentle or strong; is she well liked by her peers; does she help at home, and in what way; and what are her character traits overall.
“Do her modesty and style of dress line up with her outlook?”
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