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Is there a specific night of Chanuka that is better to give out Chanuka Gelt?

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This is an unresolved dispute. To be safe you should give out every day of Chanuka, and on the 9th day too just in case. Its best to increase the amount of Gelt given each night (except according to Beis shamai). Its also unclear what form of "gelt" you need to give, so you should use Dollars, Shekalim and Chocolate to be yotzei according to all shitos. There is another question over what currency the chocolate coins should be in, but most poskim say you can be yotzei both in shekalim and in the currency of your current medina. On the other hand, the Satmar Rebbe holds you shouldn't use ... – Ariel K Dec 20 '11 at 19:49
... Shekalim even in Israel. For more information, consult volume 2 of the Artscroll Guide to Chanuka Gelt p.366. – Ariel K Dec 20 '11 at 19:54
@ArielK I can't tell if this is Purim Torah or not! But this shitta was definitely written by the children. :P – avi Dec 20 '11 at 20:00
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The Lubavitcher Rebbes used to give Chanuka Gelt on the fourth or fifth night.

R' Chein explains that there are two reasons why one may want to give on the fifth night:
1. It never falls out on Shabbos, so one can give gelt on a consistent day.
2. On the fifth night there are more candles lit than not lit (which makes it a somewhat auspicious time).

However, some write that the custom is to give it every night, just add a little more on the fourth or fifth night.

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My grandmother would give us 1 piece of gelt for every candle lit that night. There also tended to be 1 question asked for each candle lit, including the shamesh.

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That's funny. When I was in Yeshiva I tried to eat one Sufganiyah for each candle that was lit. I made it to day 4, then wavered on day 5, and then somehow managed to eat one a day for days 6, 7 and 8 without getting sick. – Seth J Dec 20 '11 at 19:52
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My favorite question was "How many candles do we light during all of chanukah?" at which point we would get $44 if we gave the correct answer. – avi Dec 20 '11 at 20:02
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