Slaves, Their Wives and Their Children

Rashi: "If he comes alone"
meaning that he was not married, as Onkelos renders:
"he shall go out alone"
if he was not married at first, his master may not give him a Canaanite maidservant from whom to beget slaves.

if he is a married man: to an Israelite [woman].

"his wife shall go out with him"
Now who brought her in that she should go out? Rather, whoever purchases a Hebrew slave is [also] responsible for supporting his wife and his children.

Baal HaTurim: "she shall go out"
this word appears 3 times:
(1) "his wife shall leave with him." [verse 3]
(2) here, and
(3) "she shall leave his house and marry another man" (Deut. 24:2), for the acquisition of a bondswoman is comparable to getting a wife; just as a wife can be consecrated through [three methods, one of which is] the transfer of a legal document, so too can a maidservant be acquired through the transfer of a legal document.

Ramban: He who acquires a Hebrew servant must provide food [also] for his wife and children. Too, the word "with him" means that a master cannot separate him from his wife and children and thus tell him, "be together with the handmaid I gave you and sleep with her at night, and not with your Israelite wife," for the servant has the right to choose for himself.

"He comes alone, he should leave alone. If he has a wife, his wife should leave with him."
alone [in Hebrew, 'begapo'] is an obscure noun.

Onkelos agrees with Rabbi Ishmael (Mechilta) and Rabbi Eliezer b. Yaakov (Kiddushin 20a): If he arrives alone, without a wife, he leaves without a wife.

Rabbi Akiva (Mechilta), Rava (Talmud), and ibn Ezra: The word is derived from the root guf, meaning "body." If he enters servitude with his body unimpaired, he leaves unimpaired. This applies also in verse 4.

Rashi and Ibn Ezra: "If he has a wife" - whoever purchases a Hebrew servant must feed his wife and children.

Ramban: This is a rabbinic obligation, not a biblical one; biblically, the master is only required to feed the servant's family if they work for him.

Zohar Mishpatim 105:
"If he came in by himself, he shall go out by himself." If he entered the world alone, without children, and did not care to strive after that [by taking a wife] and left the world alone, without children, he moves like a stone in a sling up to that place in the strong rock. There he enters, alone, at once his spirit goes [there] solitary like a snake that does not keep company on the road.

Whereupon he leaves that place of the strong rock, alone , and roams in the world until he finds a redeemer for his improvement. That is, "If he came in by himself, he who did not wish to marry and beget children, he shall go out by himself".

But, "if he is married" he who did marry and tried with her but could not have children, such a man is not driven away like the other, nor comes out alone. But, "if he is married," G‑d does not withhold reward from anyone. Even though he did not have children, it is written, then "his wife shall go out with him". The two incarnate, and are able to unite again. He does not marry a divorced woman, but marries the same woman with whom he tried before yet they had no children. Now they shall attain it together, if they act well. Hence it is written, "then his wife shall go out with him."

BeRahamim LeHayyim:
The Holy Zohar above holds that being married is where it's at. Period. That even if one did not fulfill the mitzvah of "be fruitful [have a boy] and multiply [have a girl]", that is still OK as long as one is married and tried to have children. For if a couple tried but was unsuccessful, still the couple can reincarnate and unite again, and the next time, they will succeed to have children.

Now that is not much support for our dear infertile friends who struggle with the pain and agony of unsuccessfully trying to bear children, but it is spiritual science nonetheless. What is troubling for us post-moderns is the condemnation for the man who did not "strive" to have children, he is "like a snake that stayed alone on the road." Now in these strange times I know many men who are not married and do not have children. In fact, some of them are among the most connected and loving folks I know. Yet the Zohar is trying to reveal a mystical parable from the initial language of our Torah portion, that " if a man came in by himself [and did not marry and try to have children] then he shall go out by himself."

We know from the Talmud that if one teaches someone else Torah, it is as if he was the other's father. Maybe we students will be called to attest in their defense come Judgment Day.

Perhaps too modern engagements—that may have broken up, or modern divorce—all too common, or the death of a spouse, may count to the surviving person's spiritual accounting. Who knows?

The Zohar is trying to discourage the lone wolf life of the playboy who seeks only carnal satisfaction and pays no attention to the importance of connection to another person beyond the physical. Maybe that is the person who "If he came in by himself, he shall go out by himself".