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Introduction to Kiddush Levana: Thanksgiving
Kiddush levana expresses our thanks to God for having made the moon, which affects our lives (tides, weather, crops, biological clocks) and provides us benefits in many ways (light at night, basis for determining our calendar and our holidays).
Challot for Evening Kiddush
To use two challot for kiddush instead of wine:
  • Wash hands and say blessing al netilat yadayim.
  • Say kiddush but substitute ha'motzi for borei pri ha'gafen.
  • As soon as you finish saying kiddush, eat the bread as normal.
 
Shabbat: Your Own Kiddush Cup
As on Jewish festivals, if you want to drink kiddush wine, you may hold your own cup of wine (or grape juice) during kiddush or receive wine or grape juice from the kiddush leader's cup, but neither is required.
Yom Kippur: No Kiddush If You Must Eat
If you must eat on Yom Kippur (for health reasons), do not make kiddush and do not use two loaves of bread, even if Yom Kippur coincides with Shabbat.
Rosh Hashana: Evening Kiddush: New Fruit for SheHecheyanu on Second Night
Place a “new” fruit--over which you may say she'hecheyanu--at the table for kiddush on the second night of Rosh Hashana.
Reason So the she'hecheyanu of kiddush also covers the fruit. 
Note B'di'avad, still say she'hecheyanu even if you do not have a new fruit.
Jewish Festivals: Daytime Kiddush
To fulfill the two requirements for Jewish festival daytime kiddush:
  1. Say, or hear, at least #b and #c of these Jewish festival daytime kiddush blessings/segments:
    a) Eileh mo'adei Adonai mikra'ei kodesh asher tikri'u otam b'mo'adam.
    Note It is not a universal custom to say the above sentence.
    b) Va'yidaber Moshe eht mo'adei Adonai el bnei yisrael.
    Note It IS a universal custom to say the above sentence. AND
    c) Borei pri ha'gafen (if on wine or grape juice), OR
    She'hakol nihiyeh bi'dvaro (if on other beverage/chamar medina).
    Note For Jewish festival (or Saturday) lunch and havdala, you may use any beverage (chamar medina) commonly drunk for social purposes (not just for thirst) in the country in which you are saying kiddush (say the blessing she'hakol instead of borei pri ha'gafen where appropriate).
    Note There is never any requirement on an indvidual to drink kiddush wine (except at the Passover seder), but the kiddush wine must be drunk by one or more persons.
  2. Establish a halachic “meal” (kovei'a se'uda).
    You must establish the halachic meal required for kiddush shortly after hearing Jewish festival morning kiddush. See How To Fulfill Eating Jewish Festival Second Meal.
    Note If you make Jewish festival morning kiddush on any beverage except wine or grape juice, you must also eat mezonot or bread to establish the kiddush meal. If you do not want to eat bread or mezonot, only drinking 3.3 fl. oz. (99 ml) of wine or grape juice within 30 seconds will fulfill all of the requirements for kiddushIf you have not fulfilled the requirements for kiddush, you may not eat other foods, such as fruit or fish at a kiddush.
Jewish Festivals: Evening Kiddush
To fulfill the two requirements for Jewish festival evening kiddush:
  1. Make Kiddush
    Say, or hear, the three Jewish festival evening kiddush blessings/segments:
    1. Borei pri ha'gafen (if on wine or grape juice—preferred option), OR
      Ha'motzi (on two challot if you have no wine or grape juice, since no chamar medina is allowed for Jewish festival evening kiddush; see Jewish Festivals: Kiddush: Challot for Kiddush) AND
    2. Asher bachar banu mi kol am.... mekadeish Yisrael v'hazmanim, AND
    3. She'hecheyanu on all Jewish festival nights, except the last two nights of Passover.  So say she'hecheyanu on:
      • Both nights of Rosh Hashana (in or outside of Eretz Yisrael),
      • First two nights of Passover (1 night in Eretz Yisrael),
      • Both nights of Shavuot (1 night in Eretz Yisrael),
      • First two nights of Sukkot (1 night in Eretz Yisrael), and
      • Nights of Shmini Atzeret and Simchat Torah (same day in Eretz Yisrael).
      Note There is never any requirement on an indvidual to drink kiddush wine (except at the Passover seder), but the kiddush wine must be drunk by one or more persons.
      Note A woman who had said she'hecheyanu when she lit the Jewish festival candles does NOT say she'hecheyanu again if she makes kiddush for herself, even when making kiddush at the Passover seder.
      Note There is no need to eat a new fruit after saying she'hecheyanu on the second night of  Shavuot, Passover, or Sukkot. This is not comparable to Rosh Hashana, since the second festival night was instituted due to uncertainty of the actual date of the holiday, while Rosh Hashana is considered to be one single, long day.
  2. Establish a halachic “meal” (kovei'a se'uda).
    For how to establish a halachic meal, see Introduction to Jewish Festival “Eating a Meal” Requirements.
Note For evening kiddush, the custom is to go straight to the meal without delay (with no mezonot or snacking first).  B'di'avad if you snacked, it is still OK.
Note At night on Jewish festivals (or Shabbat), you may not say kiddush at a place where you will not eat your evening meal (even if you will hear or say kiddush again at the place where you will eat the meal).
Jewish Festival Night Kiddush Beverage
Wine (or grape juice) is the only drink permissible for Jewish festival (or Friday) evening kiddush. See Challot for Kiddush, below, if you do not have wine or grape juice with which to make Jewish festival (or Shabbat) evening kiddush.
Women: When To Make Kiddush after Candle Lighting
For when women can make kiddush after Friday night candle lighting, see Shabbat: Candles: When To Light.
 
Women: Who May Make Kiddush
For women's obligation to say or hear Jewish festival morning kiddush, see Jewish Festivals: Kiddush: Who May Make.
 
Eating before Making Shabbat Kiddush
You may eat non-mezonot and non-bread food before praying Shabbat shacharit and without making kiddush, in order to avoid hunger or hypoglycemia (low blood sugar).
Drinking Cheekful for Shabbat Kiddush
As on Jewish festivals, the minimum total volume of Shabbat kiddush beverage that must be drunk--usually by the kiddush-maker (mevareich) but it may even be by several people combined--is a cheekful (m'lo lugmov), as follows:
  • 2 fl. oz. (59 ml) within 30 seconds of beginning to drink for d'oraita cases such as Shabbat evening kiddush (as well as first-night Jewish festival kiddush and all havdalas), and
  • 1.7 fl. oz. (50 ml) within 30 seconds of beginning to drink for d'rabanan cases such as Shabbat lunch kiddush (as well as first-day Jewish festival lunch kiddush and all second-day Jewish festival kiddushes).
Note If no one drinks the kiddush beverage, a blessing was made in vain (bracha l'vatala), and the commandment to say or hear kiddush has not been fulfilled.  
Pour Revi'it for Shabbat Kiddush
As on Jewish festivals, the minimum volume of kiddush beverage on which you may say Shabbat kiddush (or havdala) is a revi'it, as follows:
  • 4 fl. oz. (119 ml) for d'oraita cases such as Shabbat (or first-day Jewish festival) evening kiddush, and
  • 3.3 fl. oz. (99 ml) for d'rabanan cases such as kiddush for Shabbat lunch.
How To Do Shabbat Daytime Kiddush
There are two requirements for Shabbat daytime kiddush: Say or Hear Kiddush Segments/Blessings and Establish a Halachic Meal (kovei'a se'uda):
 
1. Say or Hear Kiddush Segments/Blessings
    You must say, or hear, the Shabbat daytime kiddush segments/blessings and someone
     must drink at least 2 fl. oz. (59 ml) of the kiddush beverage:
  • Say or Hear Kiddush Segments/Blessings
    • Torah segment(s): V'shamru bnei Yisrael (even beginning from al kein).
    • Blessing over at least 3.3 fl. oz. (99ml) of drink:
      • Borei pri ha'gafen (if on wine or grape juice), OR
      • She'hakol nihiyeh bi'dvaro (if on other beverage/chamar medina).
   Note For Saturday (or Jewish festival) lunch and havdala, you may use
  any beverage (chamar medina) commonly drunk for social purposes (not
  just for thirst) in the country in which you are saying kiddush. The ideal is to
  use wine or grape juice.
  • Drink at Least 2 fl. oz. (59 ml) of the Kiddush Drink
  This amount may be drunk by one person or by several people together.
 
2. Establish Halachic Meal (Kovei'a Se'uda)
    You must establish a halachic meal (kovei'a se'uda) shortly after saying or hearing
    Shabbat morning kiddush by either:
  • Drinking Wine--at least 4 fl. oz (119 ml) of wine (or grape juice) within 30 seconds, OR
  • Eating Bread/Mezonot--at least 1.3 fl. oz. (39 ml, or 1/6 cup) of bread or mezonot within four minutes.
Note The second half of making kiddush, “establishing a meal” (kovei'a se'uda), can be fulfilled simultaneously when you fulfill the subsequent, separate Shabbat requirement for “eating a meal” but in that case, you must eat 1.9 fl. oz. of bread.
Note If you make, or hear, Shabbat morning kiddush on any beverage except wine or grape juice, you must also eat at least 1.3 fl. oz. (39 ml, or 1/6 cup) of bread or mezonot within four minutes to establish the kiddush meal. If you do not want to eat bread or mezonot, only drinking at least 4 fl. oz. (119 ml) of wine (or grape juice) within 30 seconds will fulfill all the kiddush requirements. 
Note If you have not fulfilled the kiddush requirements, you may not eat other foods, such as fruit or fish at a kiddush.
Note   Once you have heard kiddush and either eaten the required bread or mezonot or drunk the required 4 fl. oz. of wine or grape juice, you do not need to say or listen to kiddush again if you eat your actual meal later (except if you need to say kiddush for other people who have not yet heard or said kiddush).
Eating Only after Fulfilling Shabbat Kiddush Requirements
Once you have said the amida of Shabbat shacharit, you may not eat any food until you have said (or heard) kiddush and finished kiddush requirements by either:
  • Drinking at least 4 fl. oz. (119 ml) of wine/grape juice, or
  • Eating at least 1.3 fl. oz. (39 ml, or 1/6 cup) of mezonot or bread.