Our Gemara on Amud Aleph teaches us that, although a Jewish slave often has the option to choose to continue his servitude after undergoing the ritual of having his ear pierced, there are certain situations where he will not be allowed to remain a slave under any circumstances. This is because the verse states, "I love my master" (Shemos 21:5), implying a state of relative equivalence and harmony between master and servant. Thus, the Gemara rules:
הוּא אוֹהֵב אֶת רַבּוֹ וְרַבּוֹ אֵינוֹ אוֹהֲבוֹ – אֵינוֹ נִרְצָע, שֶׁנֶּאֱמַר: ״כִּי טוֹב לוֹ עִמָּךְ״. רַבּוֹ אוֹהֲבוֹ וְהוּא אֵינוֹ אוֹהֵב אֶת רַבּוֹ – אֵינוֹ נִרְצָע, שֶׁנֶּאֱמַר: ״כִּי אֲהֵבְךָ״. הוּא חוֹלֶה וְרַבּוֹ אֵינוֹ חוֹלֶה – אֵינוֹ נִרְצָע, שֶׁנֶּאֱמַר: ״כִּי טוֹב לוֹ עִמָּךְ״. רַבּוֹ חוֹלֶה וְהוּא אֵינוֹ חוֹלֶה – אֵינוֹ נִרְצָע, שֶׁנֶּאֱמַר: ״עִמָּךְ״
Furthermore, if he loves his master but his master does not love him, he is not pierced, as it is stated: "Because he fares well with you" (Deuteronomy 15:16), indicating that it is good for both of them to be with each other. If his master loves him but he does not love his master, he is not pierced, as it is stated: "Because he loves you." If he is ill and his master is not ill, he is not pierced, as it is stated: "Because he fares well with you," which excludes a sick person. Similarly, if his master is ill and he is not ill, he is not pierced, as it is stated "with you," which equates the well-being of the pair.
Then one Amora asks a question based on these rulings:
בָּעֵי רַב בִּיבִי בַּר אַבָּיֵי: שְׁנֵיהֶם חוֹלִין, מַאי? ״עִמָּךְ״ בָּעֵינַן – וְהָא אִיכָּא, אוֹ דִילְמָא ״כִּי טוֹב לוֹ עִמָּךְ בָּעֵינַן״ – וְהָא לֵיכָּא? תֵּיקוּ.
Rav Beivai bar Abaye raised a dilemma: If both of them are ill, what is the halakha? Do we require only that the slave be "with you," i.e., in the same condition as the master, and that is the case here, as they are both ill, and the slave can be pierced? Or perhaps we require "because he fares well with you," i.e., it must be good for both of them, and that is not the case here, as they are both ill. If so, he cannot be pierced. No answer was found, and therefore the Gemara says that the dilemma shall stand unresolved.
Ritva raises a question: since the entire process is voluntary to begin with, why do we need a verse to tell us that he does not get pierced nor does he stay if he hates his master? Ritva answers that the verse teaches us that even if he is impoverished and wishes to stay but really dislikes his master, he is not permitted to make a "marriage of convenience." He may only stay if he truly likes his master.
Returning to the unresolved question of the Gemara regarding a situation where both master and servant were equally disabled, it seems that the question revolves around the adage "misery loves company." That is, since both master and servant are unwell, is there an automatic affinity, or are they each miserable in their own unique manner?
As an interesting aside, Malbim (Shemos 2:13) uses this as a rationale to understand how Moshe knew that Dasan and Aviram were both evil. After all, why not just say the person who was hitting the “victim” was the evil one, and the other one was just fighting in self-defense? Malbim answers that it is in the nature of man when he is in dire straits to become friends with a comrade, not enemies. The fact that Dasan and Aviram were quarreling under the relentless persecution of their Egyptian overlords indicated something corrupt about both their natures.
This reminds me of something told to me by a person who had been single for a long time before she found her bashert. She said, "Often, because I was a little bit eccentric or different, people would set me up with somebody else who was offbeat and different, but to the point of social inappropriateness. They must have reasoned, well, she’s crazy and he’s crazy, so they’ll probably get along." This kind of thinking could be dangerous. Yes, in some sense we should look for certain compatibilities or complementarity when making matches, and if one person has a disability, there is rationale in looking for a partner with a disability of a similar degree. Yet, we must be careful when we do this, and we see from our Gemara’s implicit ethics, that such a strategy could still lead to incompatibility.
Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation 
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