Breaking the Fast With an Odd Number of Dates
Question

Is breaking the fast with an odd number of dates a Sunnah from the Prophet (peace and blessings be upon him)? And is eating an odd number of dates a Sunnah during Ramadan or outside of Ramadan?
Praise be to Allah.It is not established that the Prophet (peace and blessings be upon him) deliberately ate an odd number of dates or recommended doing so, except on two occasions:
The first: Before going out for the Salah of `Eid Al-Fitr.
Al-Bukhari (953) narrated from Anas ibn Malik (may Allah be pleased with him) who said: "The Messenger of Allah (peace and blessings be upon him) would not go out on the morning of `Eid Al-Fitr until he had eaten an odd number of dates."
The second occasion:
Eating seven dates in the morning.
The Prophet (peace and blessings be upon him) said: "Whoever eats seven `Ajwa dates in the morning, will not be harmed by poison or magic on that day" narrated by Al-Bukhari (5445), and Muslim (2047).
As for breaking the fast, it is established that the Prophet (peace and blessings be upon him) would break his fast with fresh dates or dry dates, and it is not established that he (peace and blessings be upon him) intended a specific number or that they be an odd number.
The Hadith reported in this regard is weak.
It was narrated from Anas (may Allah be pleased with him) that he said: "The Prophet (peace and blessings be upon him) liked to break his fast with three dates or something that fire had not touched." Musnad Abu Ya`la (3305).
This is a weak Hadith and is not established, see: "Silsilat Al-Ahadith Ad-Da`ifah" by Al-Albani (966).
Some scholars have chosen to limit this to what is established from the Prophet (peace and blessings be upon him) and not to expand in seeking to eat an odd number.
Shaykh Ibn `Uthaymin (may Allah have mercy on him) said:
"It is not obligatory - nor even a Sunnah - that a person breaks his fast on an odd number: three, five, seven, or nine, except on the day of `Eid, `Eid Al-Fitr, as it is established "that the Prophet (peace and blessings be upon him) would not go out for the prayer on the day of `Eid Al-Fitr until he had eaten dates, and he would eat them in an odd number" and other than that, the Prophet (peace and blessings be upon him) did not intend to eat dates in an odd number." End quote from "Fatawa Nur `Ala Ad-Darb" (11/2) with numbering from Ash-Shamela.
Other scholars have taken a broader view on this matter, citing the saying of the Prophet (peace and blessings be upon him): "Indeed, Allah is Odd (Witr) and He loves odd numbers" narrated by Al-Bukhari (6410), and Muslim (2677) from the Hadith of Abu Hurairah (may Allah be pleased with him).
`Abd Ar-Razzaq (5/498) narrated this Hadith and then said: Ayyub said: "Ibn Sirin used to prefer odd numbers in everything, to the extent that he would eat an odd number." And this chain of narration is authentic.
It is mentioned in "I'anat At-Talibin (2/278):
"(His statement: 'And the most complete is that it be)
 i.e., breaking the fast with dates.
(His statement: 'With three')
 i.e., with three dates, and like dates, whatever one breaks the fast with, it is Sunnah to do so in threes." End quote.
Shaykh Saleh Al-Fawzan (may Allah preserve him) was asked:
"Is the practice of eating an odd number applicable to all permissible things, such as drinking coffee and others, or is it only for things that have been textually specified?"
The Shaykh answered (in summary), "All statements and actions can be done in odd numbers; this is from the Sunnah." End quote.
Shaykh Abdul Karim Al-Khudair (may Allah preserve him) was asked:
Should one intend worship of Allah by eating and drinking (and doing other things) in odd numbers?
He answered: "Yes, one should intend worship by doing so. If one eats, he should eat one date, three dates, seven, an odd number; because Allah loves the odd number." End quote.
What supports the view that it is preferred to eat an odd number of dates when breaking the fast is the action of the Prophet (peace and blessings be upon him) in doing so on the day of `Eid, and his recommendation to eat an odd number of dates in the morning; this indicates his preference of odd numbers at the beginning of what he would break his fast with from dates and fresh dates; thus, breaking the fast from fasting is like that.
The matter in this regard is broad, in sha Allah; whoever chooses the odd number, based on the general evidence previously mentioned, and what is attested by the action of the Prophet (peace and blessings be upon him) in the mentioned instances, or finds comfort in the specific Hadith reported in this regard, despite its weakness: there is no harm upon him.
And whoever sees that breaking the fast on dates, fresh dates, and the like, should be however it happens, without deliberately seeking an odd number or not, due to the lack of specific proof from the Prophet (peace and blessings be upon him): there is no harm upon him, and this position is also clear.
And Allah knows best.