Praise be to Allah

Firstly: 

It is recommended for the fasting person to break his fast with fresh dates. If they are not available, then he should break his fast with dried dates, and if they are not available, then with water. 

This is proven from the actions of the Prophet (blessings and peace of Allah be upon him). 

Abu Dawood (2356) and at-Tirmidhi (696) narrated that Anas (may Allah be pleased with him) said: The Messenger of Allah (blessings and peace of Allah be upon him) used to break his fast with fresh dates before praying. If no fresh dates were available, he would break his fast with dried dates, and if none were available, he would break his fast with a few sips of water.

Classed as saheeh by al-Albaani in Saheeh Abi Dawood. 

Ibn al-Qayyim (may Allah have mercy on him) said: 

There is a very subtle reason why the Prophet (blessings and peace of Allah be upon him) would break his fast with fresh dates, or dried dates, or water, because when one fasts, the stomach becomes devoid of nourishment, so the liver will not find anything in the stomach that it can absorb and send to other parts of the body. Sweetness is the quickest to reach the liver and is what it prefers, especially if it is fresh, so if a person eats fresh dates, they will be absorbed quickly by the liver, which will benefit it and other parts of the body. If fresh dates are not available, then dried dates are the next best thing, because they are sweet and nourishing. If there are no dates available, then a few sips of water will extinguish the flame of the stomach and the heat of fasting, thus preparing the stomach to accept food with ease. 

End quote from Zaad al-Ma‘aad (4/287) 

Secondly: 

There is no proof in the Sunnah that the Messenger of Allah (blessings and peace of Allah be upon him) intentionally broke his fast with an odd number of fresh or dried dates. In order to follow the Sunnah, it is sufficient for the Muslim to break his fast with fresh or dried dates, without paying attention to the number or counting them. 

Shaykh Ibn ‘Uthaymeen (may Allah have mercy on him) said: 

It is not obligatory – and in fact it is not Sunnah – to break the fast with an odd number, three or five or seven or nine, except on the Day of Eid al-Fitr, as it is proven that the Prophet (blessings and peace of Allah be upon him and his family) would not go out for prayer on the Day of Eid al-Fitr, until he had eaten some dates, an odd number thereof. Apart from that, the Prophet (blessings and peace of Allah be upon him) did not seek deliberately to eat an odd number of dates.

End quote from Fataawa Noor ‘ala ad-Darb (11/2) 

With regard to the hadith of Anas, who said: The Prophet (blessings and peace of Allah be upon him) used to like to break his fast by eating three dates or something that had not been touched by fire – which was narrated by Abu Ya‘la (3305) – it is a da‘eef (weak) hadith that has not been proven. See ad-Da‘eefah by al-Albaani (966). 

There are some scholars who regard it as mustahabb to make everything odd-numbered. Shaykh Saalih al-Fawzaan (may Allah preserve him) was asked: 

Should making things odd-numbered be done with regard to all permissible things, such as drinking coffee and the like, or is it only with regard to things concerning which a text has been narrated? 

The Shaykh’s answer may be summed up as follows: 

All words and deeds should be made odd-numbered. This is the Sunnah. End quote. 

https://dl.dropboxusercontent.com/u/17891559/9959.mp3 

Shaykh ‘Abd al-Kareem al-Khudayr (may Allah preserve him) was asked: 

Will we be rewarded for making things odd-numbered as an act of devotion when eating, drinking and so on? 

He replied 

Yes, we will be rewarded for doing that as an act of devotion. So if a person eats dates, he should eat one, or three or seven, an odd number, because Allah loves that which is odd-numbered. End quote.

http://shkhudheir.com/fatawa/874254045 

‘Abd ar-Razzaaq (5/498) narrated from Ma‘mar, from Ayyoob, from Ibn Sireen, from Abu Hurayrah, that the Prophet (blessings and peace of Allah be upon him) said: “Verily Allah is One and loves that which is odd-numbered.” Ayyoob said: Ibn Sireen liked that which was odd-numbered in all things, to the extent that he would eat an odd number of things. This is a saheeh isnaad. 

This matter is broad in scope, in sha Allah, but it is not proven, as far as we know, that the Prophet (blessings and peace of Allah be upon him) used to intentionally eat an odd number when he broke his fast eating fresh or dried dates. Rather those scholars who said that said it on the basis of ijtihaad. 

Thirdly: 

The practice of the Prophet (blessings and peace of Allah be upon him) with regard to food – whether he was fasting or not – was moderate, with no extravagance or waste – as Allah, may He be exalted, enjoined. Food was never his main focus on any day; rather he would just eat a few mouthfuls to keep him going. 

When it came to food, he (blessings and peace of Allah be upon him) was not set in his ways and did not have specific things that he always did. Rather what was the case was that if he found food that he liked, he would eat it, and if he did not find it, he would remain quiet. Or if he found food that he did not like, he would not eat, and sometimes he would decide to fast. 

He never criticised any food. 

He would eat meat, bread, olive oil, honey, milk and other things that were available sometimes. 

Sometimes month after month would pass and his family would have nothing to eat except dried dates and water. 

Sometimes he would take his guest around to the houses of his wives, and not find anything but water. 

Rather his main focus (blessings and peace of Allah be upon him), and that of his companions (may Allah be pleased with them), was the hereafter and matters of religion. 

See the answer to question no. 115801 

Conclusion: 

The Prophet (blessings and peace of Allah be upon him) would eat whatever was available of his family’s food or things that were given to him as gifts by his companions and neighbours, without having any particular type of food or specific practice, except that the first thing he would eat when breaking his fast would be fresh or dried dates, and if he did not find any, he would break his fast with water, as mentioned above. 

Similarly, his sahoor (blessings and peace of Allah be upon him) was just a few mouthfuls to keep him going, and he did not seek out any particular food for sahoor, other than dates. The Prophet (blessings and peace of Allah be upon him) spoke highly of dates and said: “What a good sahoor for the believer dates are.” Narrated by Abu Dawood (2345); classed as saheeh by al-Albaani in Saheeh Abi Dawood. 

And Allah knows best.