Not Disturbing One's Children Until The Proper Time

One should not disturb one's son's or daughter's tranquillity [regarding a shidduch] before there is a concrete suggestion that is capable of being actualized and acted upon. For what possible benefit can there be [to the son or daughter] by knowing that [their parents] are thinking [about a shidduch for them].

[Aside from there not being any benefit to them from this knowledge,] it is impossible for this knowledge not to disconcert them, at least to some degree. And after all this, a concrete proposal has yet to be offered. This matter will prove particularly disconcerting, as it inevitably is connected - at least to some degree - with issues such as earning a livelihood and the like.

(Igros Kodesh, Vol. XVI, p. 114)

Not Disturbing One's Children Until Something Actually Presents Itself

... You ask me in your letter whether it would be appropriate to begin involving your son with a shidduch.

It has been my observation - both here as well as in other places - that when one begins speaking to young men about a shidduch, this immediately leads them to distraction (pizur hanefesh).

Quite often these conversations are entirely without benefit, as it takes a goodly amount of time until a suitable proposal is found, at which time the subject finally becomes of real and actual concern (nogei'a l'poel).

In light of the tender age of your son, these apprehensions and misgivings exist to an even greater degree.

It is therefore my considered opinion that when the time arrives that you want your son to actually get married and there will be an actual proposal [of a suitable person], then it is worth considering whether this proposal should immediately be presented to your son.

(Igros Kodesh, Vol. XVII, p. 274)

Not Allowing Too Much Lag Time Between The Engagement And Marriage

With regard to the content of your letter about the shidduch [of your daughter]:

I believe that I immediately expressed my puzzlement to you, mostly relating to the tender age of your daughter tichyeh.

Even more so now, after you write that "she is a very good teacher, and in order for her to receive the proper degree, she must continue her studies for some time."

Additionally, and this is of greatest import: Your suggestion that she should become engaged now and the wedding will take place after two years or a year and a half, is entirely improper. For the present generations are not similar to days past, and a girl of her age should not be bemused with such thoughts for such a lengthy period of time, from the time of her engagement till the time of her marriage.

It is also self-understood that to have her marry in just a few months would not do at all. It would seem [from your letter] that you feel this way as well.

In light of all the above, you should leave her to her own devices and studies and her sacred labor of providing children with a Jewish education. G-d will increase her measure of success in all that she does. In a little more than a year or so, she can begin interesting herself in a shidduch.

(Igros Kodesh, Vol. XIX, p. 189)

When To Meet And When Not To Meet

You write about your acquaintance with a certain young man and your intentions regarding this acquaintanceship - that it lead to a shidduch. You also remark about the positive and negative consequences of this acquaintanceship.

... You also write that in consideration of your present age, you will have to wait at least a year and then some until you will actually be able to marry.

In light of the above, it is patently obvious that this [manner of conduct] is not in keeping with my views, for such conduct is not at all consonant with the view of our Torah of Life. This is particularly so as both of you are of Sefardic extraction, where such behavior is especially not sanctioned.

Moreover - and this, too, is of primary importance - it is entirely inappropriate to be acquaintances and friends, and doing so for the purpose of marriage, and at the same time to decide that many, many months - at least - must pass before the actual marriage will take place.

As mentioned above, it is entirely inappropriate for G-d-fearing young people to become acquainted and friendly, etc., except subsequent to the time of the decision that the time for marriage has arrived.

Clearly, the directives of our Torah of Life benefit the individual not only in the World to Come, after "one hundred and twenty years," but also benefit the Jewish person in this world as well, enabling one to live a happy life materially and spiritually.

(From a letter dated Chai Elul, 5718)

When It Is Wholly Inappropriate To Meet

... You write that you are presently fifteen years old. At this age, the friendship about which you write is wholly inappropriate and entirely improper, not only in light of the directives of Torah, but even according to simple human intellect, leading as it does to entirely untoward results.

Surely, your enfeebled health and mental stress are at least partially a result of the above, or as a result of thinking about the above.

With regard to your question as to how to discontinue this friendship - the answer to this, as well, lies in that which was stated above:

It is not that you are breaking off with someone, rather you are fulfilling the directives of Torah, the Torah of Life. Moreover, this is [of benefit] not only to you, but for him as well.

If he is truly religious, he should also [understand full well that it is incumbent upon him as well to] act accordingly, doing so with a complete understanding of the directives of the Torah.

(Igros Kodesh, Vol. XXIII, p. 171)

When One Feels Entirely Unready For A Shidduch

If you have absolutely no feelings [towards the matter of a shidduch], why think of involving yourself in it at all?

You don't enter into a shidduch because of your mother's aggravation [at your not yet being engaged], or the like.

(Private Yechidus, Shevat 5730)