After mentioning a number of methods one can employ on the night of Rosh HaShana to determine if one is destined to survive the year, Abaye declares in the Gemara Kerisus 6a “Now that we have determined that Simana Milsa (symbolism is significant), one should accustom himself to eat on Rosh HaShana: gourds, black-eyed peas, leeks beets and dates”. Rashi there explains that all of these items are either sweet or grow quickly. The Tur in Orach Chaim 583 includes an esrog into the text of the Gemara.
The Tur continues that over the years various Minhagim developed to eat many more foods than the ones mentioned in the Gemara, including the famous apple in honey. Additionally, he describes the different proclamations that were recited over each of these items.
I would like to address various issues in Halacha that arise from these customs.
Some of these items could potentially be infested with insects. Clearly, the serious prohibitions against consuming bugs outweigh the Minhag of the Simanim and the infested object must either be checked and cleaned properly or not eaten. If one does not wish to miss out on one of the Simanim despite its infestation; it is adequate to place it on the table and gaze at it. In fact, the Beis Yosef writes that his edition of the aforementioned Gemara directs one to look at these foods and not to eat them at all. I have attached a number of guides on the subject. checking simanim-Rav Vaye, checking simanim-Rav Revach, checking simanim-Rav Amichai, checking simanim-kosharot
There are various Minhagim whether the Simanim are eaten both nights or only the first.
The appropriate time to eat the Simanim is after Kiddush and HaMotzi, although some have the Minhag to eat them between Kiddush and HaMotzi.
Even assuming one is following the more common Minhag of eating the Simanim after HaMotzi, though HaMotzi generally covers all of the components of a meal, nevertheless, the Mishna Berura writes that HaEtz must be said over the Simanim which are fruit.
There are numerous complicated considerations regarding which object is ideal to recite the Beracha upon. It should be observed that it is a misunderstanding to describe the issue is the order of eating the fruit. Rather, the consideration is that we wish to honor the Beracha by reciting it over the most important item. There is absolutely no difference what is eaten second, third etc.
The basic Halacha is that the first degree of priority is granted to the 7 species characteristic to Eretz Yisroel. These are, in this specific order: wheat, olives, barley, dates, grapes, figs, pomegranates. Since the first three are not traditionally from among the Simanim of Rosh HaShana, the Beracha should be recited upon a date, and it should be eaten first. There are those who eat the apple first (which probably originated because that was the only one available in most of Europe). Some Seforim justify this Minhag as relying on the opinions in Siman 211 that Chaviv (the personally preferred item) takes precedence over the 7 species. One who follows this custom should not bring the dates and pomegranates to the table until after reciting Borei Pri HaEtz to avoid the issue of going out of order.
There are various opinions whether the Simanim which are vegetables require a separate Beracha.
The general rule is that any food which is consumed as part of the meal is covered in the Beracha of HaMotzi, while something which is independent requires its own Bracha. This precept should render the Simanim obligated in a Beracha since their significance is not merely that of another course. Nevertheless, some authorities write that since they are foods which are commonly consumed as part of a meal, we should follow their general usage and not their specific purpose tonight. This largely depends upon regional and cultural considerations.
The common custom is to recite a Beracha of Borei Pri HaAdama. Some suggest that this debate can be avoided by reciting the Beracha over a banana, watermelon, etc., which are unquestionably independent of the general meal.
While it is preferable to recite the Yehi Ratzon immediately prior to eating the Siman, when it comes to the ones one is saying a Beracha upon this is impossible. It is forbidden to interrupt between the Beracha and the consumption of the food; consequently, the Yehi Ratzon should be said immediately after swallowing a small amount of the food or before the Beracha.
There are many different Minhagim regarding which Simanim are eaten, and each individual should follow his custom.
There are various Minhagim regarding the placement of the Shehechiyanu the second night of Rosh HaShana due to conflicting considerations.
The reason we eat a new fruit is because some authorities question the propriety of reciting Shehechiyanu again the second night on the Yom Tov itself. To cover ourselves, we ensure that we have a food which requires the same Beracha in which case we are obligated to say Shehechiyanu anyways, and can include the sanctity of the day itself if necessary.
Therefore, it is ideal to eat the new fruit immediately following Kiddush before washing for HaMotzi. Otherwise, if there is a significant delay, it is inconceivable that the Shehechiyanu in Kiddush would cover the new fruit, and we have failed to satisfy the opinions that Shehechiyanu did not need to be recited.
However, this can create complications regarding their Beracha Acharona. If one ate more than a Kezayis sized piece and does not eat more of the same food after HaMotzi, he is obligated to recite a Beracha Acharona before washing.
One alternative is that everyone may remain silent from Kiddush until after HaMotzi and eating the new fruit with its Borei Pri HaEtz. I suggest that it is impractical to keep the entire family quiet so long, and the fruit should be eaten before HaMotzi. We can avoid the complications incurred by either eating less than a Kezayis or remembering to have more of this fruit during the meal
The second night when the new fruit is being eaten shortly after HaMotzi to cover the Shehechiyanu and one intends to consume the Simanim again, the requirement to avoid delay trumps the precedence endowed to the 7 species, and we recite Borei Pri HaEtz on the new fruit. Some people leave the pomegranate for the second night to avoid this issue. If one is eating the new fruit before HaMotzi and the Simanim only after, since the time of the 7 species has not yet arrived there is no conflict. Of course, Borei Pri HaEtz is NOT recited a second time on the date, as the HaEtz on the new fruit covers it.