When a person eats bread at the beginning of the meal, the Beracha of "Ha’mosi" recited over the bread covers all the foods eaten as part of the meal. It does not, however, cover foods such as desserts that are eaten after the meal as an added treat, and are not served as an actual part of the meal itself. Therefore, if one eats some chocolate or candy for dessert at a bread meal, he must recite the Beracha of "She’hakol," even if he eats the dessert before Birkat Ha’mazon.
The Halachic authorities address the question of whether this Halacha applies as well to ice cream and ices. Hacham Ben Sion Abba Shaul (Israel, 1923-1998), in his work Or Le’sion (vol. 2, 12:12), maintains that one does not recite a Beracha over beverages that he drinks during a meal, even he drinks them as a dessert at the end of the meal. In his view, beverages are covered by the "Ha’mosi" recited at the beginning of the meal even if one drinks them as a dessert. Therefore, if one eats ices, which is essentially flavored, frozen water, for dessert, he does not recite a Beracha over the ices, as they are covered by the Beracha of "Ha’mosi." Hacham Ben Sion applies this ruling also to parve ice cream, which is also a frozen liquid. Ice cream made from milk, however, is considered a solid food, rather than a beverage, and therefore requires a Beracha if one eats it for dessert.
Hacham Ovadia Yosef, however, maintains that even beverages served as a dessert require a Beracha, and are not covered by the "Ha’mosi" recited at the beginning of the meal. Therefore, according to Hacham Ovadia, one must recite "She’hakol" even over ices and ice cream of all kinds that he eats as dessert at the end of the meal. Indeed, members of Hacham Ovadia’s family have reported seeing their father reciting "She’hakol" before eating ice cream as dessert at the end of a meal. (It should be noted that this debate also affects the question of whether one must recite a Beracha over coffee that he drinks at the end of the meal, an issue that has been debated by the Halachic authorities.)
Hacham Ovadia makes an exception in the case of ices or parve ice cream that one eats for dessert on Shabbat, when the meal began with the recitation of Kiddush. The Beracha recited over the wine for Kiddush covers all beverages drunk during the meal, and might cover even beverages that one drinks as a dessert after the meal. Given the difference of opinion on this matter, Hacham Ovadia advises that one who eats parve ice cream or ices for dessert at a Shabbat meal should first recite Birkat Ha’mazon. He will then be required to recite "She’hakol" according to all opinions, thereby avoiding uncertainty.
Summary: Although the Beracha recited over bread covers foods eaten during the meal, it does not cover foods eaten for dessert. Therefore, one must recite a Beracha over foods eaten for dessert such as chocolate, candies, ice cream (both dairy and parve) and ices. At a Shabbat meal which began with Kiddush, one who eats ices or parve ice cream for dessert should preferably do so only after Birkat Ha’mazon.
