Brothers

When talking about brothers the Rebbe says:

“It is my considered opinion - and this is also my response to those who inquire of me regarding this matter - that with regard to sons, one is not to impede the marriage of the younger [brother] before [the marriage of] the older [brother]. This is especially so when the younger [brother] has already attained the age of twenty. [In fact,] haste in this matter is to be lauded. The older brother should have it explained to him that assisting his [younger] brother in performing an unambiguous and obvious law of our holy Torah also constitutes the older [brother's] own performance of a clear law of our holy Torah. Thus, the merit [of his performance of this law] stands him in good stead, that he should soon obtain a shidduch as well.”

(Printed in Kfar Chabad Magazine, Issue 851.)

“... As the verse, ["This is not done] ... to give away the younger [sister] before the older [sister]," is stated with regard to daughters; your brothers sheyichyu should interest themselves in shidduchim without one waiting for the other. Surely each one of them will completely forgive the others. This [act of forgiveness] will also serve as a segulah for a good shidduch for the brother who grants the forgiveness.”

(From a letter of the Rebbe, printedm in Mikdash Melech, Vol. III, p. 53)

For parents who are in this position, it is worth reading through the letters in Eternal Joy, either in the book form or on the web at http://www.sichosinenglish.org/books/eternal-joy-1/15.htm. The Rebbe answers cases where a brother has an older sister or a sister has an older brother etc.

Siblings

I received an email some time ago regarding older siblings who are "holding back" younger ones.
Sometimes the siblings are very close in age, and the older one is not ready or cannot find what s/he needs.
Sometimes the ages are not close, but the first one has had no mazel for the moment. What should a parent do?

When a family has siblings who are close in age, it is expedient when possible to start looking for the older daughter/son early. This way one has more time to find him/her a shidduch, before the younger sister is ready too.

Of course, if the older sister is not ready and one sees no signs of readiness at all, it is more complicated. The situation of a younger sibling who feels caged in by her older sister is a very difficult one for the whole family, and parents in such situations should not leave any option untried. Talking to a Rov, davening, taking on additional hachlotos, saying tehilim, helping other Kallos, tzedokah, etc. Chazal tell us that the gates of tears are always open. May your efforts be recognized, and may all those who need shiduchim soon find their Zivug.

I know about the case of two sisters who are 15 months apart. Everyone always praised the younger one for her beauty, although the older was just as pretty, although in a different way. The parents started looking for her in the middle of Sem Aleph and she got engaged in the middle of her Sem Beis year. Then the second one got married right after.

Unfortunately as they say "man proposes and G-d Disposes" or "man tracht und G-t Lacht". If one part of the couple is not ready, our plans do not work out, but we should not start off being pessimistic. If we look for the right things, minimize our list to the max, and make ourselves the best keily we can be (do our hishtadlus) then most of the time we will be successful.

There are differences in how one deals with girls or boys. To everyone who is in this position, please consult a Rov. Present the whole case to the Rov: how old the older sibling(s) is; how long and what efforts were made to marry them off; the age of the younger sibling(s) who is ready to go; the reasons why the family believe that sibling should go first, etc.

I am going to quote some of the Rebbe’s letters on this subject from Eternal Joy (published by Sichos in English). As you can see--although the Rebbe mentions in the majority of the letters that the younger one can go ahead if certain conditions are met, the Rebbe also says in another letter that the siblings should marry in order of age. Therefore, consult with Daas Torah and do not decide on your own as you are not an objective observer and could come to an erroneous conclusion.

In these letters the Rebbe speaks about sisters, and the Rebbe tells the parents to go slowly ahead with the shidduch of the younger sibling:

“In reply to your letter in which you notify me that a fine shidduch is being suggested for your younger daughter tichyeh, a shidduch that is finding favor by all, but your older daughter tichyeh is not yet married, and you ask my opinion in this matter: You should [first] obtain your older daughter's assent regarding this matter and her forgiveness regarding her sister preceding her in a shidduch. The kishurei hatena'im [of your younger daughter] should be celebrated in a restrained manner, and there should not be too much of a rush to make an early wedding. May it be G-d's will that in the interim your older daughter will find her mate, one that is fitting for her both materially and spiritually, and you will be able to inform me of glad tidings twice over. We do not know the wondrous ways of Divine Providence. It is possible that your older daughter's overcoming her natural inclination to envy her sister and forgiving her [for preceding her in a shidduch] with a perfect heart and true joy, will remove the final obstacle and impediment, and she will find her shidduch very speedily. With blessings that the kishurei hatena'im of your younger daughter take place in a good and auspicious hour, and that you speedily be able to transmit the glad tidings of the kishurei hatena'im of your elder daughter tichyeh.”

(Igros Kodesh, Vol. IV, p. 197)

“In reply to your question about the marriage of the younger sister before the older one: Presently, during the time of the four-fold darkness of Ikvesah deMeshicha, when the "Son of David" [i.e., Mashiach] will arrive [only] after all the souls will descend from the "Storehouse of Souls" known as Guf, then if the older sister will forgive [her younger sister] with complete forgiveness, this matter [of her getting married first] has been permitted [by our Sages]. It would be advisable that this forgiveness be in writing or take place in front of two witnesses. Understandably, all this applies only if the young man is G-d-fearing, etc. It would also be appropriate that in addition to the forgiveness, the younger sister as well as the parents set aside some money for the wedding expenses of the elder sister, to be utilized when she becomes engaged in a good and auspicious hour.”

(Igros Kodesh, Vol. XV, p. 326)

But in the following letter the Rebbe sees that in this case the situation merits that the younger sibling wait:

“In reply to your letter of Monday, in which you write that up until now a shidduch has not come up for your older daughter, and a shidduch is presently being suggested for your younger daughter: You are to exert yourself to find a proper shidduch for your older daughter - it is known of the many places in which our Sages, of blessed memory, have spoken about the tremendous responsibility that lies on the father to find an appropriate shidduch for his daughters. Since our Nesi'im have been exacting with regard to the verse, "This is not done ... to give away the younger [sister] before the older [sister];" therefore, only afterwards [i.e., only after you find a shidduch for your older daughter], should you seek a shidduch for your younger daughter.”

(Igros Kodesh, Vol. VII, p. 269)