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Advent is from the Latin, "ad" = to, toward + "venire" = "come."

The most common translation into English is "Coming."

Season of the fulfillment of Old Testament expectations — as the Old Testament is interpreted by Christians!

Season of John the Baptist.

It is a season of "memory and hope" (Ratzinger). We remember how the Jews awaited a King who would restore David's dynasty and we hope for Jesus Second Advent in glory to judge the living and the dead, to restore all things and to make all things new. "All will be well, and all manner of things will be well again, I know" (Julian of Norwich).

The Two Advents of Jesus

The readings for the season of Advent operate on two different levels because there are two different comings (advents) of Jesus under consideration.

In Humility and Suffering

The season of Advent recapitulates the history of Israel and Judah (the remnant of Israel) waiting for and looking forward to the Messiah who would recreate the dynasty of King David and fulfill God's covenant with David.

The First Coming (Advent) of Jesus was his birth as a man.

Cur Deus Homo?

One of my many complaints about the Harry Potter series is that Christmas is treated as a winter holiday, utterly divorced from any spiritual meaning.

Many of my students write about "the reason for the season" in their reaction papers. None of them have ever hit the nail on the head from my point of view — I guess that is an indictment of me as their teacher! The reason for Jesus' birth was to heal a broken world, to forgive sin, and call all of us to repent and believe the Good News.

St. Anselm: "Cur Deus Homo" — "Why did God become human?"

Unbelievers are accustomed to bring this question up against us, ridiculing the basic claim of the Christian faith as absurd. Many believers ponder the question in their hearts: for what reason or need did God became man? Why did God by his own death, as we believe and affirm, restore life to the world? Couldn't He have done this by means of some other being, angelic or human, or merely by His will?

Advent is a season to be mindful of sin, both Original and personal. Much more importantly, it is a season to stand in awe of God's answer to sin: He became "he had to become like his brothers in every way, that he might be a merciful and faithful high priest before God to expiate the sins of the people" (Heb 2:17). "For we do not have a high priest who is unable to sympathize with our weaknesses, but one who has similarly been tested in every way, yet without sin" (Heb 4:15").

The priest prays at every Mass: "By the mystery of this water and wine, may come to share in the divinty of Christ Who humbled Himself to share in our humanity."

In Glory

It is a dogma of the Church, expressed in the Nicene Creed, that Jesus will "come (advent) again in glory to judge the living and the dead."

The readings at the end of Ordinary Time focus on this second Advent in Glory and reach a climax in the Feast of Christ, the King, the last Sunday of the liturgical cycle. At the end of the Church's Liturgical Year, we look forward to the End of the World.

History of Advent

Catholic Encyclopedia, "Advent":
A synod held (581) at Mâcon, in Gaul, by its ninth canon orders that from the eleventh of November to the Nativity the Sacrifice be offered according to the Lenten rite on Monday, Wednesday, and Friday of the week. The Gelasian Sacramentary notes five Sundays for the season; these five were reduced to four by Pope St. Gregory VII (1073-85). The collection of homilies of St. Gregory the Great (590-604) begins with a sermon for the second Sunday of Advent. In 650 Advent was celebrated in Spain with five Sundays. Several synods had made laws about fasting to be observed during this time, some beginning with the eleventh of November, others the fifteenth, and others as early as the autumnal equinox. Other synods forbade the celebration of matrimony. In the Greek Church we find no documents for the observance of Advent earlier than the eighth century. St. Theodore the Studite (d. 826), who speaks of the feasts and fasts commonly celebrated by the Greeks, makes no mention of this season. In the eighth century we find it observed not as a liturgical celebration, but as a time of fast and abstinence, from 15 November to the Nativity, which, according to Goar, was later reduced to seven days. But a council of the Ruthenians (1720) ordered the fast according to the old rule from the fifteenth of November. This is the rule with at least some of the Greeks. Similarly, the Ambrosian and the Mozarabic Riterites have no special liturgy for Advent, but only the fast.
"Those Were the Days of Giants ..."
But long gone are the days of a forty day fast beginning on Nov 12. The observances were every bit as strict as Lent. St. Martin's Feast Day was a day of carnival (which means literally “farewell to meat” (carnis + vale)). In those days the rose vestments of Gaudete were really something to rejoice about, since the fast was relaxed for a day. Then back into the fast until Christmas. Lent too began with Mardi Gras (fat Tuesday), as the last of the fat was used used up and the fast was enjoined beginning the next day.
And the fast and abstinence were far more than the tokenary observances we have today. In most places, all animal products were strictly forbidden during Advent and Lent. There were many regional differences about the rest of the details. While most areas permitted fish, others permitted fish and fowl. Some prohibited fruit and eggs, and some places like monasteries ate little more than bread. In some places, on Fridays of Lent and Advent, believers abstained from food for an entire day; others took only one meal. In most places, however, the practice was to abstain from eating until the evening, when a small meal without vegetables or alcohol was eaten.

Advent Rage

Advent is a season of great sorrow and great joy, much happiness and much frustration. We want things to be nice. We want families to love one another. We want to give and receive gifts joyfully. Some of us become angry and intemperate about the sins we see in others: consumerism, commercialism, materialism, shallowness, manipulation, loss of the religious dimension of Christmas, vapid seasonal music, neglect of the family, resurrection of old resentments, etc. It's one of the tricks and strategies of the enemy to get us to pay more attention to others' sins than to our own — and to forget that this is precisely why Jesus became human. What we see and reprehend is what He saw and came to heal.