Which questions exactly should I ask when making inquiries about a candidate?

He sorts the inquiries into blocks. Family and background: what kind of family it is, whether the relationships are close, whether there are obligations to relatives. Future in-laws: are they emotionally healthy, do the parents have a healthy marriage, do they speak respectfully to each other, does the father have a daily shiur, how are they seen in shul, do they keep their word, will your child be comfortable with them, do they push unsolicited advice, would your child turn to them for support. Then values and beliefs, goals and plans, interests, style of communication and conflict resolution, routines and habits, history of relationships and friendships, willingness to grow and admit mistakes. About a young man he suggests finding out his plans, his connection with a mentor, his learning and davening, his attitude to family, money, alcohol, responsibilities and frustration. A concrete example: where can he be found on a Thursday night, asleep, learning or out with friends? About a young woman he suggests asking about reliability, maturity, the ability to give in, communication, tznius, consumer expectations and her relationship with her phone. Both lists include questions about reactions to discomfort and about the vision of the future marriage. Some of the items ask for subjective assessments and predictions, so they remain the author's questions rather than established facts about a candidate.

“Do the parents have a healthy marriage? Do they speak respectfully to each other?”

A father came to ask him about a bachur for his daughter: how diligent is he, does he speak up in shiur, how learned is he, is he strong in analysis and in original explanations, is he one of the illuyim, are his learning partners illuyim. As he was leaving, the father heard a question: and whom, exactly, was this bachur proposed for? For me, he answered. Precisely, said the rav: you are not looking for a good husband for your daughter but for a prominent chassan for yourself. When one seeks for the father-in-law, one asks whether he is a scholar; when one seeks for the girl, the main questions are about character: how he behaves in the dormitory and the dining room, whether he is considerate of others.

“you are trying to find a prominent chassan for yourself!”

Ask first of all about character, personality traits, life goals and values. And ask specific questions rather than general, subjective ones; that way you will get much closer to the truth.

“Asking specific questions, rather than general, subjective ones will more likely get you closer to the truth.”

Do not be afraid of very specific questions, and prepare them in advance: instead of asking whether she likes doing chesed, ask what chesed exactly she does, and ask for examples. Her own list: where and how long have you known the person; does he plan to learn long-term; the most striking features of his character; does he smoke; what should he work on; how does he plan to earn a living; an academic mind or practical street smarts; vacations; has there been a serious loss in his life, and did he see a professional; was there a broken engagement; physical, mental and emotional health; medications; what he does to relax; where he wants to live.

“Here is a list of questions you may want to ask during your inquiries”

Matches are made in Heaven, and the most unexpected combinations produce wonderful marriages, but a sensible educator or parent understands what his child needs and which spouse would be harmful; when such a person asks precise questions, it is clearly not a whim, and the answer must be precise too. Questions must be specific: general ones are an invitation to misunderstanding. One man's talmid chacham is another's am ha'aretz, and a forty-year-old mother of seven understands neatness quite differently from a newlywed; the words good, neat and friendly measure nothing. But whether he comes to shiur on time and whether he makes his bed in the morning leave almost no room for error.

“One man's talmid chacham is another's am ha'aretz.”

To get an answer to relative questions, find someone who knows both of you: only such a person understands what exactly you mean by sweet, refined, religious, good in learning, a sense of humour, outgoing. Outgoing: the life of the party, or simply able to hold a conversation? Good in learning: can translate the text, or knows Shas at his fingertips? Religious: keeps Shabbos, or stringent in everything? Someone who knows you will understand what you are really asking.

“your next step should be to try to find someone that knows both of you”

Similar-sounding English phrases from two mashgichim meant the exact opposite: one was praising an outstanding bachur, the other was saying that during davening the young man stands outside in the corridor. Hence his rule: answers must be followed up and pinned down with specifics, does he skip davening, does he attend the mussar shiur, how is he with people, and one should ask someone one trusts personally.