- Is he a morning person or a night owl?
It is sometimes hard for a night owl to get along with a morning person; when one is up and chipper, the other only wants to sleep, and when one is just getting going, the other is drooping, so it is a valid question.
- Does he make friends easily?
This question might have already have been answered by one of the previous questions.
- What do you consider his best quality? (subjective question)
It is helpful to hear what friends and family find admirable in a boy.
- What do you consider his worst defect?
Be weary of repeated: "He is such a wonderful boy I cannot think of anything at all!" No one is perfect, if they cannot think of anything it may mean that there is something they do not want to say, and it is so big in their mind they cannot come up with a minor infraction they can say. Therefore if one person cannot think of anything, it may happen but if more than one gives you such an answer ask a few more people.
- What kind or a drinker is he? How does he behave after a few drinks?
As mentioned previously, in Lubavitch many boys drink at Farbrengens, is that something we should worry about? We are not talking here of alcoholics, Ch V’Sh. So why would we even ask? Well, some of us do not like the results of drinking. We do not wish to have our husband brought home after a Farbrengen, more unconscious than not, and we do not wish to deal with the aftereffects of a hang over. Others, do not mind and do not think it is necessarily a bad thing if occasionally they go overboard. Therefore, it really depends on whether this kind of drinking bothers your girl or not. You should look into it at least to make sure that there is no real drinking problem and go vaiter. (This is one of the 3 things mentioned in the Gemora, see above)
Another concern to keep in mind: Some boys and girls are projecting an image. He is considered the best bocher, a baal chessed etc. She is considered a leader in her clique, cheerful, studious, outgoing etc.
These girls and boys could be acting in a certain way because of their present surroundings. They know a certain behavior is expected and they provide it. But if taken out of these situations, do they have the personal resources to be what they project or is it only an image? Is he truly studious or it is part of his image to sit with a sefer and he thinks of ______ (pick your subject) while looking at the open sefer. Is she enterprising in public but not at home? Even more, is he/she courteous to friends and strangers but abrupt and unfriendly with family?
When looking for a shidduch for your child do not be taken in by an image. Make sure that what you get from your inquiries are solid answers and not the usual patter of “he is a wonderful boy...” “she is a great girl...”. And when your child goes out she should not be taken in by pretty manners put on show for the date, see how he behaves with waiters or attendants, parking valets etc. The same way people will not be totally truthful on a job application, similarly young people will act in the accepted way publicly so that they may get married.
Some may act more frum than they are, some may stop trimming a beard just for a shidduch etc.
Caveat: We should not go crazy checking every last thing, after all sometimes from "shelo lishmo bo lishmo" they have acted a certain way so often they get in the habit of it. The point is if there is a particular thing you are makpid on, do diligent research. I repeat: one particular thing, let us not go overboard and consider everything particular.
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