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23:31 ① Do not look at wine when it is red; ② when he puts his eye on the cup, ③ it goes smoothly.

① Do not look at wine when it is red =  Do not put your eye on it.

② When he puts his eye on the cup, it goes smoothly:  = Whoever is habitually drunk-all transgressions appear to him to be straight (smooth); all ways appear straight.

on the cup: Heb.. The Masoretic text reads: on the pocket; i.e., the drinker puts his eye on the cup, and the storekeeper puts his eye on this ones pocket.

Moral Instruction

Don’t be influenced by the sight of beautiful red wine, the seller often adds red coloring to the glass that he pours. The seller's eye is on the customer's pocket. He wants the customer to put his eye on the glass and buy more wine.

Practical Advice

Food coloring is a substance that is added to food to improve its external appearance; it enables the seller to sell at a higher price. Usually it has no nutritional value, and can even be harmful. Food Coloring is alluded to in our verse:

① Do not look at wine when it is red  = Do not look too much at the beautiful red color of wine.        

② when he puts his eye on the cup,

Eye = means organ of vision, also means color, tone or appearance of something        

When he puts his eye on the cup  = The pourer "gives eye" or adds color, appearance to the cup before pouring the wine to make it seem redder; And as a consequence the client too puts his eyes on the cup.    

③ it goes smoothly.

Smoothly  = directly, without opposition, and uninhibited;       

it goes smoothly =  When the customer sees the beautiful color, appearance, he goes directly to the seller and buys the wine. Or: The wine goes directly into his mouth. The color, appearance helps to remove inhibitions and resistance to the purchase.          

In the written version the verse has both words

kos       Means cup

kis        Means pocket

The customer puts his eyes on the cup [kos], and the shopkeeper puts his eyes on the pocket [kis]" ( Leviticus Rabbah 12:1 , Rashi), this is the main purpose for the food coloring.

The result of adding red coloring to the wine - (in the next verse) is:

32 At the last it bites like a serpent, and stings like a basilisk.

In food coloring there is some fraud; a deception of our instincts. Our body is accustomed to judge the quality of foods on the basis of their color and appearance among other things; an artificial change in color may cause us to consume foods that are not fit.

Parallels in Torah

This verse is reminiscent of the verse on the tree of the knowledge of good and evil in Genesis 3:6-7:

❶ And in Genesis 3:6-7:

6 And the woman saw that the tree was good for food and that it was a delight to the eyes, and the tree was desirable to make one wise; so she took of its fruit, and she ate, and she gave also to her husband with her, and he ate.

7 And the eyes of both of them were opened, and they knew that they were naked, and they sewed fig leaves and made themselves girdles.

❷ Proverbs 23:31-32:

31 Do not look at wine when it is red; when he puts his eye on the cup, it goes smoothly.       

32 Ultimately, it will bite like a serpent, and sting like a viper.  

In both accounts there is mention of a snake; according to Rabbi Meir, the Tree of Knowledge was grapes. Talmud. (Berachot 40).

In this parallel we can find an answer to the famous question: Why was man not allowed to eat from the tree of knowledge of good and evil. Didn't God want man to be intelligent?! The answer is, the tree of knowledge is like wine: when you take a little thought gets sharper, but when you take too much, delusions and hallucinations begin, this is expressed by the next verse:

23:33 Your eyes will see strange women, and your heart will speak confusedly. our eyes will see strange women: When you will become drunk, they will burn in you and entice you to ogle harlots.

❸ This corroborates the view of Raba who said: Wine and spices have made me wise.

"The tree of knowledge is good in a small quantity but bad in large quantities; It gives one a feeling that he knows good and evil, but like with wine, this feeling is only an illusion.

Subtleties

①  Do not look at wine when it is red;

This verse states this in a negative connotation, but there are those that have learned something positive from it: when you drink wine for a mitzvah (for example the four cups of Passover, or libation on the altar), that wine should have a nice color.

            ① R. Judah said: It must possess the taste and appearance of wine. Said Raba, What is R. Judah's reason? Because it is written, Look not thou upon the wine when it is red.11

            11 Prov. XXIII, 31. Thus it does not merit the name wine unless it has its appearance too.

Pesachim 108

            ② Now who is it that rules that one may not bring [old wine]? Obviously Rabbi; yet it says ‘But if one did bring it, it was valid’! — Rather said Raba, this is the reason for Rabbi's view; it is written, Look not thou upon the wine when it is red.11

            11 Prov. XXIII, 31. Hence red wine is the choicest; but after one year the wine loses its redness and brightness.

Menachot 87

            ③ R. Kahana the father-in-law of R. Mesharshya inquired of Raba: May white 22  wine [be used as a drink-offering]? — He replied unto him: Look not thou upon the wine when it is red. 23

            22. V. p. 405, n. 8.

            23. Prov. XXIII, 31. This implies that proper wine must be red. Hence, only red wine may be used for drink-offerings.

            And this is the ruling in the Shulchan Aruch

Baba Bathra 97

Excessive alcohol drinking can cause bloodshed.

            ④  Raba said: Look not thou upon the wine ki yith'addam: look not upon it, for it leads to bloodshed [dam].33

            33. [H] translated 'when it is red,' is taken as reflexive of [H] 'blood'.

Sanhedrin 70

③ it goes smoothly

In a negative sense, hints at addiction:

❶ Before addiction - the buyer is pleased with the beautiful color of the wine in the glass , he reaches directly  (immediately) into his pocket to buy the wine, because "he desires to increase his drinking, after he puts his eye on the cup" (Rabbi Yonah).

❷ The addiction itself - after the buyer begins to drinks, he releases all mental inhibitions: "one who is often drunk - all his offenses are to him like a plain, all roads are straight in his eyes" (Rashi, according to Yoma 75), especially in the area of intimacy "  (Leviticus Rabbah 12a).

            When it giveth its color in the cup, when it glideth down smoothly . 23 R. Ammi and R. Assi [dispute concerning it], one said: Whosoever fixes  his eye in the cup, 1 all incestual intercourse appears to him like a plain; 2 the other said: One who indulges in his cup, the entire world appears to him like a plain .3 Care in the heart, boweth it down. 4

            23 Prov. XXIII, 31.

            1 The Talmud takes the passage in this sense: When he puts his eye i.e., devotes his attention to the cup, when he is drunk.

            2 ‘Mesharim’ (‘smoothly’) is connected with Meshor, ‘a plain’.

            3 In his drunken state the man overlooks all handicaps to his desire, be they directed against illicit intercourse or against his neighbor's property.

            4 Prov. XII, 25.

[Talmud:Yoma 75]

❸ After the addiction - the house remains empty and flat like a plain, after the drunkard sells all his possessions in order to  get wine:

In the end his house he will permit a forbidden relation.

Do not look at wine when it is red; when he puts his eye on the cup, it goes smoothly.

B. In the positive meaning:

❹  As long as the buyer only looks  at the wine, only puts his eyes on the glass, he still walking in the plains (smoothly): The moment he puts his mouth to the wine, he can no longer go straight (smoothly).

❺ If the buyer gives the glass of his intellect, that is  he thinks well about the consequences of his drinking, and will also give pocket of his intellect, that is he thinks well about the cost, then there is a chance that he will walk straight (smoothly) and will not drink too much (according to Moshe David).

Cup , Purse and Anger

            R. Ila'I 3 said: By three things may a person's character be determined: By his cup,4 by his purse 5 and by his anger; and some say: By his laughter also.

            (4) Sc. by the effect of drink on his mind, or by the amount he consumes.

Eruvin 65

The commentators did not mention upon what Rabbi Ilai based himself, but there seems to be a hint that it comes from this verse:

Do not look at wine when it is red; when he puts his eye on the cup, it goes smoothly

When it is written "when he puts his eye on the cup" . The read word is cup kos (cup) the written  is kis   (pocket), and he gives his eyes = ayin = the letter "ayin" . If we put an ayin between  כס  we get kaas heaven forbid anger.

(Rabbi Yaakov Shechter)

My Commentary

① If the body is as a country then eyes are like the country's high officials.

If the officers are straight, all is well with the country. Likewise, when the eyes are guarded the mind and body are enhanced. The eyes perceive, observe, judge, appreciate the beauty of the world.

If the officers are corrupt beware for the country. Similarly when the eyes are corrupt from looking at wine, or immodest images etc., beware for the body.

② The seller adds coloring to the wine to trick none other than the eyes of the customer. The eyes are the ones that are susceptible to being tricked.

The possible result of eyes being tricked is an addiction to wine, or to vice (including gazing at immodesty). That is why the next verse reads:

"Ultimately, it will bite like a serpent, and sting like a viper."

This verse is compared to Genesis 3:6-7 where Adam and Eve ate of the forbidden fruit.

It was the eyes that tricked Eve into thinking the fruit was a delight.  After they ate they knew they were naked, their eyes were opened.

This verse tells us that our eyes are susceptible (compromised, weakened) to temptation and has to be guarded.

③ In my opinion the fact that wine must have a nice appearance means that although it has the potential to harm we should not make it unattractive,

We have guard ourselves, our hearts and our eyes, so that we do not fail. In the Shema which we read in the morning and in the evening every day:

"...and you will not follow the desires of your heart and your eyes which lead you astray"

Personally I think lost is a most destructive thing.   I keep away from immodest images as if they are poison (which they are) and my reward is very great. All of the emotion I would have wasted on immodest images is mine to use as I want with my friends, family, doing positive things I enjoy.

How do I keep away from it?

Talmud Kidushin 30b. Even so did the Holy One, blessed be He, speak unto Israel: ‘My children! I created the Evil Desire, but I [also] created the Torah, as its antidote; if you occupy yourselves with the Torah, you will not be delivered into his hand."