(Note: this is a collection of the meanings attributed to the cards by some occultists in the past centuries. It does not reflect my own study or opinion of the cards. It is only meant as a quick comparative reference as I develop my own take.)

Paul Foster Case (and Ann Davies)

The Two of Cups, astrologically, is assigned to the first decanate of Cancer, ruled by the Moon, time period June 22 to July 1.
The specific divinatory ideas associated with this Key are:
Well Dignified: reciprocity, reflection; gain and benefit through parents;
favors from the opposite sex; changes of residence.
Ill Dignified: reverses and losses through parents or the opposite sex; unfortunate changes of residence; fluctuations of mood; unwise decisions.
Keyword: Response to environment.
(From the Oracle of Tarot course)

A. E. Waite

A youth and maiden are pledging one another, and above their cups rises the Caduceus of Hermes, between the great wings of which there appears a lion’s head. It is a variant of a sign which is found in a few old examples of this card. Some curious emblematical meanings are attached to it, but they do not concern us in this place. Divinatory Meanings: Love, passion, friendship, affinity, union, concord, sympathy, the interrelation of the sexes, and–as a suggestion apart from all offices of divination–that desire which is not in Nature, but by which Nature is sanctified.
(From The Pictorial Key to the Tarot)

Aleister Crowley

The Two always represents the Word and the Will. It is the first manifestation. Therefore, in the suit of Water, it must refer to Love, which recovers unity from dividuality by mutual annihilation.

The card also refers to Venus in Cancer. Cancer is, more than any other, the receptive Sign; it is the House of the Moon, and in that Sign Jupiter is exalted. These are, superficially, the three most friendly of the planets.

The hieroglyph of the card represents two cups in the foreground, overflowing upon a calm sea. They are fed with lucent water from a lotus floating upon the sea, from which rises another lotus around whose stem are entwined twin dolphins. The symbolism of the dolphin is very complicated, and must be studied in books of reference; but the general idea is that of the “Royal Art”. The dolphin is peculiarly sacred to Alchemy.

The number Two referring to Will, this card might really be renamed the Lord of Love under Will, for that is its full and true meaning. It shows the harmony of the male and the female: interpreted in the largest sense. It is perfect and placid harmony, radiating an intensity of joy and ecstasy.

Of necessity, the realization of the idea in the Four (as the suit develops) will gradually diminish the purity of its perfection.
(From the Book of Thoth)

Golden Dawn’s Book T

A WHITE Radiant Hand, issuant from the lower part of the card from a cloud, holds lotuses. A lotus flower rises above water, which occupies the lower part of the card rising above the hand. From this flower rises a stem, terminating near the top of the card in another lotus, from which flows a sparkling white water, as from a fountain. Crossed on the stem just beneath are two dolphins, Argent and Or, on to which the water falls, and from which it pours in full streams, like jets of gold and silver, into two cups; which in their turn overflow, flooding the lower part of the card. Venus and Cancer above and below.

Harmony of masculine and feminine united. Harmony, pleasure, mirth, subtlety:
but if ill dignified — folly, dissipation, waste, silly actions.
Chokmah of HB:H (Marriage, love, pleasure).
Therein rule the Angels HB:AVa’aAL and HB:ChBVYH.

Etteilla

Love
Upright. This card, as far as the medicine of the spirit is concerned, means, in its natural position: Love, Passion, Inclination, Sympathy, Attraction, Propensity, Friendship, Benevolence, Affection, Attachment, Taste, Bonding, Galantry, Attraction, Affinity.
Reversed. Desire, Augury [= Aspiration], Vow, Will, Want, Cupidity, Concupiscence, Jealousy, Passion, Illusion, Appetite.

MQS