Can a gay man who will likely never be married wear a Tallit Gadol during Shacharit and a Kittel during Rosh Hashonah , Yom Kippur, and for those who have that custom, on the night of Pesach?
Rabbi Shmuel Gelbrad in his Otzer Taamei Haminhagim (Rite and Reason in English, translated by Rabbi Nachman Bulman and published by Mifal Rashi Publishing) brings down that the majority of Ashkenazic communities are accustomed that men may wear a tallit gadol only after they get married and brings several reasons for this custom. He similarly explains that this is the custom as well with regard to a kittel though he avoids directly dealing with the reason of why only married men wear one.
There is a very clear and accepted precedent in halacha, brought in numerous sources for accepting extra minhagim (customs) on oneself. A classic example is wearing a gartel (a ritual belt worn by most chassidik Jews). While many are not born into a family with this custom, it is clearly accepted that there is no problem with taking it on.
Further, the Mishna Brura (17:3) clearly paskins that a man should wear a tallit gadol from the age of 13 onwards and is very surprised by the minhag some ashkenazi communities have of waiting for the time of marriage.
Therefore, it would seem that if someone wanted to take on this minhug, there would clearly be no halachik difficulties given that many sephardic and even some ashkenazik communities already accept it.
The question of a kittel however is somewhat more difficult. While Rabbi Gelbrad does not discuss any reasons why unmarried men do not wear a kittel (the only reason I have ever heard is related to one reason he explains for wearing one at all: The kittel will remind a person of the garments that a person is wrapped in at the time of death and will cause him to remember that death could be close by and to do teshuva. Since a married man has a family to support, he will feel this closeness much more than the single man who has fewer responsibilities.), it would seem clear that there are no communities which are accustomed to allowing unmarried men to wear a kittel.
While technically it is not prohibited to do so, we have a general rule of minhagim that we do not accept new ones on ourselves which no one else does unless the person is a leader of the generation. A classic example is Rabbi Sheinberg, Shlita, one of the leaders of the generation who lives in Jerusalem. He is accustomed to wearing almost 300 pairs of tzitzit with every single different twist and turn of every single different custom. However, if the average person were to do such a thing, people would look at him as someone who is haughty and showy, as if to say, "I'm so much holier than the rest of you that I do things no one else does." Therefore, when there are no communities that allow such a minhug, we generally do not allow a person to take it on.
However, the case of a kittel is slightly different.
The talmud in tractate Brachot 17:B brings the case of a man who wishes to recite the Shema on the night of his wedding. The rabbis (majority opinion) say he may do so while Rabbi Shimon Ben Gamliel uses the above principle to say that he should not be showing off to say I can do things that most people wouldn't do. The talmud goes on to explain that the reason the rabbis permitted saying shema on the night of the wedding is because he would simply be doing what everyone else is doing and therefore would not stand out even though technically he should not be required to do this.
A parallel may be drawn to our case. Even though technically an unmarried man has no requirement to wear a kittel, since he would simply be doing what everyone else was doing and so would not especially stand out, it may be permissible for him to wear a kittel if he so desires. An important piece of information to remember however is that when accepting upon yourself these minhugim, you are making an oath to always follow them which may never be changed unless you specifically have in mind that this should not be an oath or if you go before a special rabbinical court to ask for permission to remove this oath.
As with all my svorot l'halacha, I must ask that as much as possible, you please do not take this on face value and first look into the sources and see if this makes sense to you and only then decide whether to follow this or not.
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