One blessing over wine precedes the betrothal ceremony, another the nuptials ceremony. Because the two ceremonies retain their own integrity even though united, two cups of wine should be used for the two blessings over wine. The Tosafists add that since in ancient times the betrothal took place in the bride's home and the nuptials in the groom's (at different times), the two separate cups recall that history. The law also holds that one should not recite two prayers of ke'dushah over one cup, for mitzvot should not be bunched together; each deserves respect. While two wine glasses are definitely preferred, one may be used and then refilled.

The source for the drinking of wine is not explicitly stated in the Talmud, though some rabbis presume that it is implied. She'iltot is the basis of the final halakhic decision that it is preferred at the betrothal, but that only at the nuptial ceremony is it definitely required. Only kosher wine should be used and placed, sealed, under the chuppah alongside the two wine glasses. If kosher wine is not available, whiskey, beer, or the equivalent should be used.

Who should drink the wine was a subject of much debate. Some authorities held that the person who reads the blessing, the rabbi, should proceed to drink that for which he recited the blessing, and then serve it to groom and bride. Others held that only the couple need drink the wine; still others maintain that the rabbi drinks, but the bride and groom should not. Today it is customary that only the bride and groom drink the wine, as they are in fact performing the mitzvah, and the rabbi's blessing is recited on their behalf. While it is not necessary for the bride and groom themselves to recite the blessing, it is entirely proper that they recite the amen after the rabbi's blessing.

The wine need not be drunk entirely, only tasted. An interesting innovative suggestion is that when the couple sips the wine after the nuptials, when they are legally married, the groom should himself present the wine to his wife as the first demonstration of his obligation to support his wife. These are nuances of custom, however, and there are many possible variations.

Wine, in the Jewish tradition, is closely associated with the Sabbath and with festivals. At the onset of the Holy Day, wine ushers in the spirit of sanctity, kiddush, and at the end wine closes it, havdalah. This accomplishes a significant task: It marks the boundary lines and separates the holiness of the Holy Day from the secular character of the ordinary day. At the wedding, the wine symbolizes both kiddush, sanctity, and havdalah, separation, as the blessing itself indicates: "...who has sanctified us with His commandments and commanded us about [some say 'separated us from'] illicit relations…" As wine is used at the threshold of the Sabbath to sanctify it and to separate it, so it is used at the threshold of marriage to separate it from the prohibited and to sanctify the bonds of proper marriage.

Wine is associated in Jewish tradition with shirah, song and festivity. As such it is appropriate to joyous occasions like the Sabbath and marriage. Both are not only to be observed, but need to be celebrated. Marriage is very similar to the Sabbath. Both are covenantal, reciprocal love relationships. Abraham Joshua Heschel describes a rabbinic allegory:

"[Rabbi] Shimeon ben Yohai said: After the work of creation was completed, the seventh day pleaded: 'Master of the Universe, all that Thou has' created is in couples; to every day of the week Thou gayest a mate; only I was left alone.' And G‑d answered: 'The community of Israel will be your mate.'

"When the people of Israel stood before the mountain of Sinai, the L-rd said unto them: 'Remember that I said to the Sabbath: The community of Israel is your mate. Hence: Remember the Sabbath day to sanctify it' (Ex. 20:8). The Hebrew le'kadesh, to sanctify, means, in the language of the Talmud, to consecrate a woman, to betroth… With all its grandeur, the Sabbath is not sufficient unto itself. Its spiritual reality calls for companionship of man…"

This companionship is demonstrated anew every week: the custom of Rabbi Yanai was to put on special robes on the eve of the Sabbath and then address the day: "Come O bride, come O bride."

The Sabbath is a bride and its celebration is like a wedding. The Midrash makes many comparisons: "Just as a groom is dressed in his finest garments, so is man on the Sabbath; as a man rejoices all the days of the wedding feast, so does man rejoice on the Sabbath; just as man does no work on his wedding day, so does a man abstain from work on the Sabbath day; and therefore the Sages and ancient saints called the Sabbath a bride."

As the Sabbath was like a wedding, so the wedding took on characteristics of the Sabbath. Wine signaled the sanctification. As the Sabbath sanctified the day, investing the commonplace with the mystery and grandeur of holiness, calling activities such as eating and sleeping oneg (delight), marriage is able to sanctify the mundane routines of life with the sense of the holy and to endow personal relationships with the character of covenant. The sanctity of marriage means embracing life and elevating it to the level of the sacred. As the Sabbath made a sanctuary of time, marriage must make a sanctuary of a human relationship.

The saintly Shelah drew more specific comparisons: There are seven blessings in both the Sabbath silent devotion and in the nuptials. The central prayers are those of ke'dushah—the Sabbath devotion's ata kidashta, and the wedding's kiddushin. There is recognition of the quality of joy, simchah, in both—on the Sabbath the prayer yismach moshe, and the same'ach te'samach blessing at the wedding. As the Sabbath has an "additional" service, mussaf, the wedding contract prominently contains an "additional" commitment of support, tosefet ketubah.