The Halacha states that under certain conditions, one recites the Beracha of "Hatov V’hametiv" when drinking a second glass of wine that is superior to the first. Yet, the Shulhan Aruch (175:3) rules that if one has two wines in front of him, of different qualities, he should make the Beracha of Hagefen on the superior wine and that will exempt the inferior one. Accordingly, under ideal circumstances, the first cup is always the superior wine, and the second glass is not eligible for the Beracha of "Hatov V’hametiv."
Sometimes, people make Kiddush on a cheap wine, even though they plan to drink a good wine during the meal. This is problematic, since the Beracha should be recited on the better wine, even though he will not be able to say Hatov V’hametiv.
Hacham David has a Chidush that if he has a justification to use the cheap wine first, he may recite Hagefen on it. For example, one may prefer to start the meal with a lighter wine, or the children who drink from the Kiddush prefer the cheaper wine. Additionally, if the cheap wine is not Mevushal (Pasteurized) it is preferable for Kiddush over the fine pasteurized wine. In such cases where the second wine is superior, it is eligible for a Beracha of "Hatov V'hametiv," provided that the other conditions are met.
SUMMARY
In general, one should recite the Beracha of Hagefen on the finest wine he plans to drink, even though he will not be able to say "Hatov V’hametiv on the second glass. If he has a reason to recite the Beracha on the inferior wine, he may do so, and then the next glass of superior wine is eligible for the Beracha of "Hatov V’hametiv."
