55:1 If a person has a large variety of fruits in front of him and he wants to eat some of each type, if they all have the same bracha, he should recite it over the one he desires the most. If he has two favorites and one of them is of the seven species for which Israel is praised, then that one takes priority. This is the case even if that fruit is only partial and the others are whole. If neither is of the seven species but one is whole and the other isn’t, the whole one takes priority. [The Mishnah Brurah rules otherwise. He says that the seven species and whole vs. partial each takes precedence over one’s personal preferences. See MB 211:4 and 211:13.] If one fruit’s bracha is ho’eitz and the other’s is ho’adomah, he must recite both brachos. In this instance, he would say the bracha on his favorite first. If he likes them equally, the seven species of Israel take precedence over other species, or a whole fruit takes precedence over a partial fruit as in the previous scenario. [See Mishnah Brurah 211:9 and Bi’ur Halacha there that one should say the bracha on the fruit he normally prefers.] If both are whole or both or partial, then ho’eitz has priority over ho’adomah.
55:2 If all of the fruits are of the seven species of Israel and one likes them all equally, one would follow the order in which the fruits are named in Deuteronomy 8:8. The word “land” occurs twice in that verse and we count separately after each. Therefore, dates come before grapes because dates are #2 in the second list and grapes are #3 in the first list. This only applies to grapes, not to wine. Wine has its own bracha and it takes priority over all kinds of fruit.