There are various credible minhagim regarding these matters, and it is not our place to imply that one should abandon his minhag in favor of a different one. We will simply explain the issues at hand, although we will show mild preferences for certain practices for the benefit of those who lack a clear minhag.
The gemara[2] states that since symbolism has significance, one should “be in the practice” of eating[3] certain foods – dates and four vegetable simanim – in the “beginning of the year.” Some maintain that the “beginning of the year” refers to all Rosh Hashana meals, whereas others hold that it refers only to the first meal. The more accepted practice is to eat the simanim at both night meals.[4]
The more prevalent minhag (as well as the one preferred by poskim) is to eat the simanim foods after HaMotzi.[5] In addition to the natural logic of eating the foods during the meal, some poskim claim that doing so solves a halachic problem.[6] If one were to eat the simanim before the bread, he would put himself into a situation in which it is questionable whether the simanim foods require their own beracha acharona. This is similar to the question that arises regarding eating karpas before matza during the Pesach seder.[7] We solve that problem by eating less than a k’zayit of karpas,[8] but many people want to eat more than a k’zayit (combined) of the simanim.
On the other hand, eating the simanim after bread raises other berachot questions. The poskim assume that one makes a beracha rishona on the fruit simanim even though they are eaten during the meal. However, this is not self-evident.[9] Although fruit eaten as desert requires a beracha rishona, no beracha is recited on fruit served as an “appetizer.”[10] One would think that since the simanim are served in the beginning of the meal, they should be considered an appetizer. Perhaps the fact that the simanim are eaten for ritual and not culinary reasons is a contributing factor to justify a beracha requirement.[11]
A related question is whether to recite Borei Pri HaAdama on a vegetable siman. As a rule, we do not make a beracha on vegetables during a meal, as they “accompany the main meal.”[12] In our case, however, there are varied opinions. The more common practice is to make the beracha, perhaps because the vegetables are eaten as simanim, but some posit that their status as simanim makes no difference.[13] Some compromise and maintain that one recites the beracha on the vegetable least normally eaten as part of the meal, which some assume is kara (of the gourd family).[14] (Piskei Teshuvot[15] cites Rav Devlitzki as suggesting a safe, although unnatural, idea – making the beracha on a Borei Pri HaAdama fruit, such as a watermelon or banana, which certainly is not eaten as part of the main meal, making recitation of the beracha more clearly required.)
Another question of minhag vs. regular rules of berachot relates to the order of the simanim. When one plans to eat multiple fruit and at least one of them is of “the seven species,” which includes both dates and pomegranates, he should recite Borei Pri HaEtz on that fruit.[16] (If he is eating more than one fruit of the seven species, the question of on which to make the beracha is determined based on the order in which the seven species appear in the pasuk.[17]) Nevertheless, the common minhag among Ashkenazim is to first eat the apple dipped in honey, with a beracha and with a Yehi Ratzon.[18] Some take the purist approach, reciting Borei Pri HaEtz on the date and having the apple only later.[19] One way to preserve the order of the Yehi Ratzon prayers and still follow the regular rules of berachot is to be careful to keep the dates and pomegranates off the table when making the beracha on the apple, while having in mind to eat them afterwards.[20] Another option is to make the beracha on the date, eat a small amount without reciting the Yehi Ratzon, and then eat the apple, pomegranate, and more date, etc., following the order that fits the standard practice.
Although it is contrary to common practice, poskim recommend that when eating a food on which a beracha is recited, one should take a small bite of the food right after the beracha and recite the Yehi Ratzon only afterwards, before further eating.[21]