For an explanation of the methodology of this series, see the introduction.

"A widow, a divorcee, a woman who is profaned or a prostitute, he shall not marry [any] of these. Only a virgin of his people may he take as a wife." (Levit. 21:14)

Peshat (basic meaning):

Rashi: "a woman who is desecrated"
"Desecrated" here refers to [a woman] who was born from those unfit for the priesthood.

Remez (hinted meaning):

Baal HaTurim: "in her virginity [in Hebrew, 'Be’betuleha']" (from the previous verse)
[The letters denoting "in her"], the Beit (= 2) and the Yud (= 10), are superfluous, for it could be written "a virgin [in Hebrew, 'betula/']". The Torah uses the longer form to hint to 12 years [2 + 10], the age until which a woman's physical signs of virginity remain intact.

Derash (interpretive meaning):

Ramban: This means he is not to wed a woman who is not a virgin, this being a negative commandment derived from a positive one, and thus carries the force of the positive one. He forbids the High Priest by means of a negative commandment to marry a widow or any other disqualified woman, thus commanding him in a positive sense to take a virgin as a wife.

...a marriage which is prohibited by the Creator...cannot be a happy one...

Lubavitcher Rebbe : In all matters of matrimony, the happiness of two partners is involved, and if there is any issue between them, the happiness of children and future generations is at stake. Obviously a marriage which is prohibited by the Creator and Master of the Universe is one that cannot be a happy one, and is certain to be harmful to all parties. In other words, if the said kohen has feelings for the divorcee in question, he should realize that his marrying her would expose her to untold harm not only in the afterlife and in spiritual sense but also in this physical life.

The fact that it is beyond comprehension is immaterial, for it is certain that the Creator of the world knows what is best for His creatures, and since He has so strictly prohibited such a marriage, there can be no doubt that it is harmful. Therefore even on humanitarian grounds, the said kohen, if he has any feelings for the said divorcee, [for that reason also] should give up the idea and avoid causing himself and her irreparable damage, physically and spiritually. (From a letter)

Sod (esoteric, mystical meaning):

Zohar Emor 90:
"but he shall take a virgin of his own people as a wife".

A priest...must be...wholesome in body, whole in his wife...

The Faithful Shepherd opened and said, this commands the High Priest to marry a virgin, as said, "A widow, or a divorced woman, or a profaned, or a harlot, these shall he not take; but he shall take a virgin of his own people to wife." Why is it necessary for him to marry only an unblemished virgin? A woman is a cup of blessing, tasted is blemished. A priest who offers a sacrifice before G‑d must be whole and unblemished …in limbs, because blemishes make priests unfit. He should be wholesome in body, whole in his wife, so as to fulfill in him the verse, "You are all fair, my love; there is no blemish in you." (Song 4:7)

For the sacrifice is a gift. Israel need to send their gift to the King by a wholesome man, as they are the opposite of the Other Side, to which they would send a gift by an appointed man who is blemished, as written, "one lot for G‑d, and the other lot for Azazel." (Lev. 16:8) For other gods are all blemished on the northern side. In this way most heathen households are defective in respect to their wife, a ruin, Lilit, blemished, etc.

BeRahamim LeHayyim:
The word Betulah/virgin is sometimes used to symbolize the Feminine Divine Presence, and She is unblemished, even though She is with us in exile which is full of impurity.

The Above Zohar reveals the secret of why the High Priest must marry only a virgin: A woman is a cup of blessing, tasted is blemished, like a cup of wine that has been tasted. It tastes fine, may indeed be quite remarkable, but cannot be used for blessing purposes. 1

For a cup of blessing is just that—a vessel that contains the flow of beneficent radiance from the Almighty that is poured on the fortunate receptacle below. When we ask for a blessing, we seek to draw the sacred energy from our Maker to influx and fill up an area that needs light. And what is the greatest receiver—the feminine, the female, the woman, malchut, the Shechinah.
Women below represent the Shechinah Above.
Women below represent the Shechinah Above. They have more innate "holiness" than any man can aspire to, both in the role of "receiver" as well as that of "giver,", for they birth life, something that only the Divine can authorize.

All of this is upped tremendously when we concern ourselves with the idea of the Kohen Gadol, whose exemplary service facilitates the flow from Above to below. He, of all, needs to remain absolutely pure in all he does below.

A woman who is not a virgin is not physically blemished, but since she has received from another source—another male—she is not at a sufficient level of purity for the Kohen Gadol to give forth to her his personal Shefa/flow.

The job of the High Priest is to bless, and all of his being is for that end. For him not to avail himself of all that is of the highest caliber adds potential disruption to the science of the sacred flow.

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