When we mention the FOUR QUESTIONS in any Jewish context, most assume it has to do with Pesach’s Mah Nishtana. But the FOUR SHIDDUCH QUESTIONS are applicable for the entire year.

One of the most frequently asked questions of me, by parents and singles alike, is “What should I be asking when I’m checking someone out?” In another blog, we’ll cover when to check someone out and how much checking to do. However, before agreeing to a first date, everyone should ask a few questions – FOUR QUESTIONS – so you don’t burn out by going out with the wrong people.

Remember that before you start the dating process, you will have already identified three criteria for agreeing to a first date. Now you want to ask questions that will help you determine if those criteria are met. For that, it is best to ask FOUR specific questions, and make sure they are open-ended questions. To decide whether to go on a first date, here are FOUR basic questions to ask.

Wait – hold on. Before you even get to the first question, you should be asking the premise question to the shadchan suggesting the match, whether it is a professional or amateur matchmaker: Why are you suggesting this shidduch?

Sometimes, the response will be, “I don’t know, just a gut feeling”, and to be honest, I have made some successful shidduchim based on that. But aside from those rare exceptions, you should be hearing answers that match your three “must haves”, your three priorities to say yes to a suggestion and compel you to agree to the match. If a matchmaker does not know the single they are suggesting, don’t waste your time. If someone wants you to take an idea seriously, they need to present it seriously. If you were looking for a job as a nurse, you wouldn’t want to take 100 calls from headhunters offering you secretarial work. If you were looking to buy a home in New York, you wouldn’t waste your time with realtors in Alaska offering you homes. Don’t waste your time with people who sign up for websites or email lists, click some buttons or randomly send emails of people who are totally inappropriate for you. Stay focused. Be serious. And be treated seriously. Or else you will waste your time, burn out, and hate the dating process even more than you already do!

The next few questions should be asked of the shadchan but also of references.

Question 1: What do you think he/she needs?

Here’s the problem in shidduchim. Sometimes a shadchan, or a reference, is so keen to help a single they know date, that they’ll try to make everyone be appropriate for you. They’ll ask you what you are looking for, and then make the potential date fit. Don’t let them happen here. Immediately ask the open-ended question of – what do you think he or she needs? Note, this is not about what the person says he or she is looking for, but rather needs. As you listen, think to yourself, are they are describing you?

Question 2: WHY do you say/think that?

This question is asked when a shadchan is describing personality traits of a prospective match. For example, the shadchan will say, She/he is such a nicer person. You want to ask an open-ended question – why do you think that? Please give me an example what makes this person nicer than someone else.

Or it could be asked in response to a shadchan saying someone is smart. Kind. Generous. Whatever the personality trait is. Remember, sometimes people do chessed because they are not married and have time to pass. Joining lots of chessed committees is not a sign that someone is very nice. You want the examples that show people are nice when no one is looking. Like the guy who stays after shul to put away the siddurim or chumashim others left behind. That is a genuinely nice guy. Not the person who signs up for every committee, sometimes out of boredom, sometimes for honor or glory. And yes, someone can sign up for chessed organizations and activities because they are genuinely nice. But you want to hear personal experiences and stories, not what you can already read on the shidduch resume.

Question 3: HOW do you see that?

This is asked in response to hashkafic/religious practice questions. Someone is modern orthodox machmir. Yeshivish. Modern yeshivish. How do you see that? Do you see it in dress? Behavior (i.e. do they watch movies, use the internet)? Someone is described as a Ben Torah – how?

Let’s be clear, people are often using the wrong terms to describe hashkafa. “Yeshivish” does not mean someone is learning in yeshiva all day. It means they follow yeshivish Rabbis. They follow the  Gedolei HaDor, the leaders of the yeshiva world. “Modern yeshivish” does not mean someone went to yeshiva but now works. Someone could be yeshivish and work in klei kodesh, or they could be yeshivish but also a doctor or lawyer or other professional. Modern yeshivish means that they don’t adhere to all the practices of the yeshivish world – they probably watch movies (here and there or more than that), they don’t dress in black and white, etc. Are you looking for a Ben Torah, someone who prioritizes Torah even if they have a professional job all day? Are you looking for someone modern orthodox, who may go mixed swimming or a girl who doesn’t plan to cover her hair after marriage? Don’t let someone just throw out a hashkafic term to you, but ensure that they explain what it means for the specific person they are suggesting to you.

Question 4: What would you say are his or her chisronos (weaknesses) that he/she needs someone to balance out with strengths in those areas? This is not designed to be lashon hara and to help you look for problems. Rather, it is to show you how you could partner with your spouse to help each other be better people. No one is perfect. How could you, working together, make a great team? For example, if someone is a neat freak, they would likely clash with someone who is super-messy. But if someone is borderline neat or messy, they need someone to push them over the top just a little, to be encouraging, to help them be a little neater or a little less freaked out by a small mess here or there. And someone who is more introverted may be looking for a partner who is quiet, but others who are very quiet and introverted may be looking for a more outgoing partner to help bring them out of their shell.  This is something fair to understand from the get-go.


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