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In Chapter 2 of the Mishnah Torah on Repentance, the Rambam presents an achingly romantic view of "Complete Repentance" (doubly romantic as it involves love between both a man and a woman and a man and Hashem):

אֵי זוֹ הִיא תְּשׁוּבָה גְּמוּרָה. זֶה שֶׁבָּא לְיָדוֹ דָּבָר שֶׁעָבַר בּוֹ וְאֶפְשָׁר בְּיָדוֹ לַעֲשׂוֹתוֹ וּפֵרַשׁ וְלֹא עָשָׂה מִפְּנֵי הַתְּשׁוּבָה. לֹא מִיִּרְאָה וְלֹא מִכִּשְׁלוֹן כֹּחַ. כֵּיצַד. הֲרֵי שֶׁבָּא עַל אִשָּׁה בַּעֲבֵרָה וּלְאַחַר זְמַן נִתְיַחֵד עִמָּהּ וְהוּא עוֹמֵד בְּאַהֲבָתוֹ בָּהּ וּבְכֹחַ גּוּפוֹ וּבַמְּדִינָה שֶׁעָבַר בָּהּ וּפָרַשׁ וְלֹא עָבַר זֶהוּ בַּעַל תְּשׁוּבָה גְּמוּרָה. הוּא שֶׁשְּׁלֹמֹה אָמַר (קהלת יב א) וּזְכֹר אֶת בּוֹרְאֶיךָ בִּימֵי בְּחוּרֹתֶיךָ

What is complete repentance? He who once more had in it in his power to repeat a violation, but separated himself therefrom, and did not do it because of repentance, not out of fear or lack of strength. For example? One who knew a woman sinfully, and after a process of time he met her again privately, and he still loving her as theretofore, and he being in a state of potency, and the meeting is in the same land where the sin was first committed, if he parted without sinning, he has attained complete repentance. Of such Solomon said: "Remember then thy Creator in the days of thy youth" (Ecc. 12.1)" (Translation from Sefaria)

What, however, would be the logistics of such a demonstration of complete repentance? Would yichud be required? If so, would one get a "pass" for committing this transgression in order to seek complete repentance? If one or both parties had divorced in the meantime, would the repentance be any less complete?

If yichud is required, would that not be a serious transgression of the following principle set forth in Avodah Zarah 17a (as well as elsewhere):

עולא כי הוה אתי מבי רב הוה מנשק להו לאחתיה אבי ידייהו ואמרי לה אבי חדייהו ופליגא דידיה אדידיה דאמר עולא קריבה בעלמא אסור משום לך לך אמרין נזירא סחור סחור לכרמא לא תקרב

The Gemara relates: When Ulla would come from the study hall, he would kiss his sisters on their hands. And some say: On their chests. And the Gemara points out that this action of his disagrees with another ruling that Ulla himself issued, as Ulla says: Mere intimacy with a woman with whom one is prohibited from engaging in sexual intercourse is prohibited, due to the maxim: Go, go, we say to a nazirite, go around, go around but do not come near to the vineyard. Just as a nazirite is warned not even to come into close proximity of a vineyard lest he consume a product of the vine, so too one is obligated to distance himself from anyone with whom intercourse is forbidden." (Translation from Sefaria)

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R. Ephraim Luntschitz indeed explains (Kli Yakar Bamidbar 19:21) that the penitent must seclude himself with the woman that he previously sinned with. He thus explains the statement of the Sages that in the place where penitents stand even the wholly righteous cannot stand: the penitent must seclude himself with the woman in order to repent but the righteous individual is not allowed to seclude himself with the woman.

ויש אומרים שזה כוונת חז"ל במקום שבעלי תשובה עומדים צדיקים גמורים אין יכולים לעמוד שם כי הבעל תשובה צריך לעמוד במקום אשר עמד שם בראשונה ולהתיחד עם אותה אשה אשר חטא אבל לצדיק גמור אסור היחוד כי אסור להביא נפשו בנסיון נמצא שיחוד דהיינו עצם התשובה מטמא הטהורים ומטהר הטמאים

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  • How antinomian!
    – Double AA
    Commented Mar 20, 2018 at 0:02
  • Well, @DoubleAA, that's not a sin that can very well be repeated/shrunk from in the middle of a crowded coffeeshop, is it? Commented Mar 20, 2018 at 2:31
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I think this question is a mistake (notwithstanding the checked answer!) The Rambam doesn't say or mean that you are supposed to do this. He simply describes examples of two different kinds of situations, one where the test is as severe as it was originally, one where the test is much easier to pass. Let me add more of the quote from above:

וְאִם לֹא שָׁב אֶלָּא בִּימֵי זִקְנוּתוֹ וּבְעֵת שֶׁאִי אֶפְשָׁר לוֹ לַעֲשׂוֹת מַה שֶּׁהָיָה עוֹשֶׂה אַף עַל פִּי שֶׁאֵינָהּ תְּשׁוּבָה מְעֻלָּה מוֹעֶלֶת הִיא לוֹ וּבַעַל תְּשׁוּבָה הוּא. אֲפִלּוּ עָבַר כָּל יָמָיו וְעָשָׂה תְּשׁוּבָה בְּיוֹם מִיתָתוֹ וּמֵת בִּתְשׁוּבָתוֹ כָּל עֲוֹנוֹתָיו נִמְחָלִין

[Whereas] if he does not repent until his old age, at a time when he is incapable of doing what he did before, even though this is not a high level of repentance, he is a baal-teshuvah. Even if he transgressed throughout his entire life and repented on the day of his death and died in repentance, all his sins are forgiven...

If you pass the first type of test it is called teshuvah gemurah, for you have completely demonstrated that you have changed. If you do teshuvah in the second situation, you are not being tested as severely (or at all, as on the day of his death), but it counts as well.
The Rambam is not giving advice here, or orders. He is explaining how forgiveness works.

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