Haircut during the thirty days to avoid obstruction for Tefillin
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Question
A mourner within the thirty days for his brother, whose hair is very long, is he allowed to cut his hair to avoid obstruction for Tefillin?
Answer
A mourner should not cut the hair on his head even if he fears it may be an obstruction, and he should not comb the hair against its natural growth.
Source
There is a disagreement between the Rosh and the Rashba regarding whether there is a prohibition of obstruction for the Tefillin on the head. In the Shulchan Aruch, Orach Chaim, Siman 27, סעיף 4, it is written: "There should be nothing that obstructs between the Tefillin and the body, whether on the hand or on the head." In the Mishnah Berurah, there, סעיף קטן 16, it is written that even the straps necessary for tying the Tefillin should be without obstruction beneath them, where possible.
The Machatzit HaShekel writes: "For this reason, I am disturbed by those who grow long hair, besides the fact that it is a way of pride and arrogance, and there is a slight prohibition as written in Yoreh De'ah, Siman 178, סעיף 1, it is also forbidden when placing Tefillin, since they are too long to say that it is their natural growth, and they obstruct. And even according to the Rashba, who said that in practice we do not pay attention to obstruction on the head, in such a case, perhaps the Rashba agrees. And as it is forbidden for him to wear a thick hat, as written in MA, סעיף קטן 7, because it is not called placing on the place where the softness of the infant's head is. The same applies to long hair, they are like a thick hat." This is also brought in the Mishnah Berurah, there, סעיף קטן 15.
In the Aruch HaShulchan, Orach Chaim, Siman 27, סעיף 14, it is written: "There are those who want to be stringent even when the hair is very long, and I do not see any reason in this, because how can you set a boundary for the length of hair, and the hair on the head is considered as part of the head. Perhaps if he has long hair that also surrounds the sides of the head, in this case, there is certainly an obstruction, but not in the natural hair growing in this place, and this is the simple custom, and there is no need to doubt this."
However, the later authorities questioned the opinion of the Machatzit HaShekel, that hair is an obstruction, and do not say that it is their natural growth, how can a Nazirite wear Tefillin? And they answered that since his commandment is to grow the hair, in the case of a Nazirite, all agree that it is their natural growth. And so in the case of a mourner, who is forbidden to cut his hair, since it is his commandment, it is certainly their natural growth.
However, in the Kitzur Shulchan Aruch, Siman 191, סעיף 12, it is written: "It is forbidden to shave his hair all thirty days, whether the hair of his head, the hair of his beard, or the hair on any place. And for his father and mother, it is forbidden to shave until his friends rebuke him. And regarding the measure of rebuke, there is a disagreement among the authorities, and in these countries, it is customary not to shave all twelve months, unless for necessity. For example, if his hair becomes too heavy for him, or if he goes among the nations and becomes disheveled among them due to his hair, then it is permitted to shave." From his words, it is clear that in a case of necessity, when "he goes among the nations and becomes disheveled among them due to his hair," he is permitted to shave after thirty days even without rebuke.
And to satisfy those who hold that even hair is an obstruction, he should not comb the hair on his head to the sides but let them grow as they are in their natural state, and thus even according to the Machatzit HaShekel, there is no prohibition of obstruction unless he moves the hair not in their natural state, such as combing them backward, etc.
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