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Suppose there was a man, A, that underwent an operation whereby afterwards A now considers themselves female. Suppose one is generally unclear as to the specifics of the operation, but that A definitely now consider themselves female (e.g female clothing, restroom, etc.).

May a man be in yichud with A? Is it different if one did know the specifics of the operation (i.e is there a specific boundary that has any halachic significance)?

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    Does transgender surgery have any halachik status? I would think not. – ephraim helfgot Feb 4 '16 at 2:09
  • Related (although not a dupe, and not comprehensive enough to answer this question): judaism.stackexchange.com/questions/57490/transgender-erva Also related, and possibly able to help with this question: judaism.stackexchange.com/questions/34058/… – Salmononius2 Feb 4 '16 at 2:10
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    @ephraimhelfgot Please see the second link from my comment above. There is an opinion of the Tzitz Eliezer that says surgery does affect halachic status. – Salmononius2 Feb 4 '16 at 2:11
  • Because we now assume that the Jews of their previous gender will be 'interested' in them? I would posit that, most of the time, this is not the case. – ephraim helfgot Feb 4 '16 at 2:17
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    I think it is worth also exploring the counterpart: can she be in yichud with other women? – Shimon bM Feb 4 '16 at 2:46
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This is an interesting question. I have not an absolute answer but perhaps some matter for right thinking.

  1. Androgynos

    Let us have a look at the Tosefta called "Androginos" (known as 4th chapter of Massechess Bikurim) The androginos bears similarities with males and with females. In matter of Ychud he does not have the right to be alone with men or with women. Before we start, we draw attention to the fact that Yichud between two men is allowed. We do not suspect benei Israel for this "לא נחשדו ישראל על כך". But if there are strong suspicions, then, automatically, we get a strong prohibition. For example kutim are suspected. Here is an extract of our Tosefta:
    ‏ -ב כֵּיצַד שָׁוֶה לָאֲנָשִׁים. מְטַמֵּא בְלֹבֶן, כָּאֲנָשִׁים. וְנוֹשֵׂא, אֲבָל לֹא נִשָּׂא, כָּאֲנָשִׁים. וְאִמּוֹ יוֹשֶׁבֶת עָלָיו בְּדַם טֹהַר, כָּאֲנָשִׁים. ‏ ‏ וְאֵינוֹ מִתְיַחֵד עִם הַנָּשִׁים, כָּאֲנָשִׁים ‏‏. וְאֵינוֹ נִזּוֹן עִם הַבָּנוֹת, כָּאֲנָשִׁים. וּמִתְעַטֵּף, כָּאֲנָשִׁים. וְעוֹבֵר עַל בַּל תַּקִּיף וְעַל בַּל תַּשְׁחִית וְעַל בַּל תִּטָּמֵּא לְמֵתִים, כָּאֲנָשִׁים. וְחַיָּב בְּכָל הַמִּצְוֹת הָאֲמוּרוֹת בַּתּוֹרָה, כָּאֲנָשִׁים: ‏
    He is not entitled to isolate with women, as a men are not.
    ג כֵּיצַד שָׁוֶה לַנָּשִׁים. מְטַמֵּא בְאֹדֶם, כַּנָּשִׁים. ‏ ‏ וְאֵינוֹ מִתְיַחֵד עִם הָאֲנָשִׁים, כַּנָּשִׁים ‏ ‏ . וְאֵינוֹ זוֹקֵק לְיִבּוּם, כַּנָּשִׁים. וְאֵינוֹ חוֹלֵק עִם הַבָּנִים, כַּנָּשִׁים. וְאֵין אוֹכֵל בְּקָדְשֵׁי הַמִּקְדָּשׁ, כַּנָּשִׁים. וְאִמּוֹ יוֹשֶׁבֶת עָלָיו בְּדָם טָמֵא, כַּנָּשִׁים. וּפָסוּל מִן הָעֵדוּת, כַּנָּשִׁים. וְאִם נִבְעַל בַּעֲבֵרָה נִפְסַל מִן הַתְּרוּמָה, כַּנָּשִׁים: ‏
    He is not entitled to isolate with men as women are not.
    As says @magicker72 (and I am very grateful to him for the knowledge) the Rambam in Issurei Bia chapter 22, Halacha 11 wrote that mans are permitted with tumtum and androgynoss.
    ‏ אַנְדְּרֻגִּינוֹס אֵינוּ מִתְיַחֵד עִם הַנָּשִׁים; וְאִם נִתְיַחַד--אֵין מַכִּין אוֹתוֹ, מִפְּנֵי שְׁהוּא סָפֵק. אֲבָל הָאִישׁ מִתְיַחֵד עִם הָאַנְדְּרֻגִּינוֹס, וְהַטֻּמְטוֹם. ‏
    An androgynos may not enter into privacy with women. If he does, he is not given physical punishment, because his status is doubtful. A man may enter into privacy with an androgynus or a tumtum.

    The Kesef mishney noted the discrepancy with the Mishna and give a Teruts.
    But the fact that the Magid Mishne see on Rambam a citation of the Tosefta is the proof that Rambam has a different version of the Tosefta. In responsa 130 Rabbi Menachem Azaria Mipano wrote, because he is not "spousable for a man", men departed from him. And when they see that he can spouse women, they consider it as a male. And Israeli men are not prohibited to enter in privacy with men. There is a broad spectrum of cases. If the androgynos he looks so much like a women, he do not enter in privacy with men. In the Shut he reported a Sugia in Masechet Yebamot: See Mishna Yebamot 8, 6:
    • רַבִּי יוֹסֵי וְרַבִּי שִׁמְעוֹן אוֹמְרִים, אַנְדְּרוֹגִינוֹס כֹּהֵן שֶׁנָּשָׂא בַת יִשְׂרָאֵל, מַאֲכִילָהּ בַּתְּרוּמָה. ‏
      Rabbi Jose and Rabbi Simeon stated: if a priest who was an hermaphrodite married the daughter of an israelite, he confers upon her the right to eat terumah. {this was the first opinion of Rabbi Yosi, but in Berayta he changed his view and said that Androgynos is a being apart, and they do not decide what is his gender}
    • רַבִּי יְהוּדָה אוֹמֵר, ... אַנְדְּרוֹגִינוֹס נוֹשֵׂא, אֲבָל לֹא נִשָּׂא. ‏
      Rabbi Judah stated: ... the hermaphrodite may marry [a wife] but may not be married [by a man]. {he is a mal and a man which penetrate it in which way is punished for homosexual intercourse.}
    • רַבִּי אֱלִיעֶזֶר אוֹמֵר, אַנְדְּרוֹגִינוֹס חַיָּבִים עָלָיו סְקִילָה, כְּזָכָר:‏
      Rabbi Eliezer stated: [for copulation] with an hermaphrodite the penalty of stoning is incurred as [if he were] a male.{do not agree with Rabbi Yehuda for an intercourse not typically homosexual}
    wrote explicitly that
    • if androgynos looks like a women it is prohibited in Yichud with men,
    • and if he has a penis obviously he is prohibited int Yichud with women.
    And he said this also according Rambam, and despite he considered that in the version of the Tosefta of the Rambam androgynose's Ychud is allowed.
  2. Transgender

    • Transgender is a man that want to be confused with a women and is obviously prohibited in Yichud with men.
      In conclusion it seems prohibited. One would think that transgenders and androgynes are roughly equivalents from the point of view of Yichud with mans. At first glance this seems obvious.
    • On the other hand, the fact that male which become which "female transgender" had no right to be alone with women is less obvious. But if he is technically able to have sexual intercourse with a woman, i.e. with erection (not "משמש באבר מת") Yichud is very probably prohibited with women.
    • I don't know, in cases where male sexual organ has been amputated, he can not have sexual relation with women ("ראוי לביאה או אין ביאתו ביאה") and I happen to believe that Yichud is allowed. (without being directly linked to Halacha, this recalls of the eunuchs harem wardens).

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    But see EH 22:12 that permits yichud of a man and an androgynus, and the Khelkat Mekhokek explains that this is because Jews aren't suspected of sexual impropriety with a safek zachar. The Beit Yosef suggests that Rambam (and those that follow his ruling here) had a a different girsa of the barayta. – magicker72 Feb 4 '16 at 15:33
  • I really modified the answer, with a little documentation. – kouty May 12 '16 at 16:46
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In ילקוט יוסף, אוצר דינים לאשה ולבת, פרק נ"ו, he writes about gender change surgeries. He initially discusses whether a woman would still need a get if her husband had a gender change surgery done and now considered himself a woman.

He then writes regarding the permissibility of performing such a surgery:

ועכ"פ ברור שאסור לאיש לעשות ניתוח כזה, דמלבד שמפקיע מעצמו מצות האיש (אף שיש לעיין דשמא עדיין חייב בכל המצוות כאיש) גם עובר על איסור סירוס, וא"צ להאריך בזה, ופשוט דהוא אסור ע"פ ההלכה.

In other words, it is forbidden to do the surgery because one will be removing himself from the obligation to do the mitzvos that a man is obligated to do (although he writes that it is possible that he is still obligated to do all the mitzvos incumbent upon men, despite his surgery).

The implication is that by doing the surgery he is effectively a woman and no longer obligated in mitzvos that are specifically for men. Therefore one might thing that Yichud should apply. However he himself is not completely sure as he adds that perhaps the person is still obligated in mitzvos. It is clear however that his primary inclination is that the surgery is effective.

Presumably at least as a safek R' Yosef would rule that Yichud applies.

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    He doesn't appear to mention Yichud at all. – Double AA Apr 5 '16 at 5:04
  • True, hence my last sentence: since his default position is that the person is no longer obligated in Mitzvos that apply to men, the extension of this is that the person is now considered a woman - how else could they now be absolved from all Mitzvos for men? He only parenthetically states that perhaps they remain obligated in those mitzvos - in other words, they remain a man for purposes of halacha. Therefore his default position, that they are considered a woman, presumably applies at least mi'safek to Yichud... – nagah Apr 6 '16 at 4:05
  • That would all be dandy if not for the fact that Yichud is not solely determined by Halachic gender. Things are not always so black and white where we can say that a person's practical gender for one issue must be the same as other issues. – Double AA Apr 6 '16 at 4:25

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