If you have already heard of תדיר ושאינו תדיר תדיר קודם -- frequent and not frequent, frequent first -- and are surprised by the title, you are welcome to skip to the end, but please hear me out. If you are not so familiar with the topic, let's start with a short introduction.
In those cases where two obligations come up for a single event, this rule determines which comes first. For example, in bentching there are additions for both Shabbos and Rosh Chodesh. On Shabbos Rosh Chodesh, you will perforce say one before the other; halacha neither requires nor even condones speaking different things out of both sides of your mouth. The rule of תדיר ושאינו תדיר תדיר קודם tells you to say the addition for Shabbos first, and then the addition for Rosh Chodesh. This also comes up in the chapter of psalms we say after morning prayers. The extra psalm for Rosh Chodesh -- which is said 18-ish times a year -- comes after the daily psalm -- which is said 52-ish times a year.
What about לדוד/Psalm 27? It is said every morning and afternoon/evening for the 51-ish day period of the Days of Awe. Does that trump the psalm for Rosh Chodesh, which is only said 18-ish days? Or do we say that the psalm for Rosh Chodesh is said 12-ish times a year and Psalm 27 is only said once a year? It is the second way. Those who like to learn mussar from everything note that an action repeated over a longer period of time is more effective than an action performed more intensely, but for a shorter period of time.
Here's a cool/novel application of this halacha from R' Shlomo Zalman Auerbach, z"tzl: We read the megilos of Rus, Shir HaShirim and Koheles before the Torah reading of the appropriate Yom Tov. R' Shlomo Zalman Auerbach explains this is because of תדיר ושאינו תדיר תדיר קודם. The reading of the megilos is a minhag and we want everyone to know that it is a minhag and not an obligation. If we were to read the megilah after the Torah, then people would say, "Oh, I get it. תדיר ושאינו תדיר תדיר קודם. Since the Torah is read more often, that's why the megilah is being read afterward." By reading the megila before the Torah reading, though, people will say, "Ah! Reading the megila must just be a minhag, because if it were an obligation, then it would come after the Torah reading because of תדיר ושאינו תדיר תדיר קודם." (You see from here also the high esteem in which the rav held all Jews, expecting them to think through everything they saw going on in shul with such sophistication.)
Ok... Now that we are all back together. Eating a סעודה -- even the "סעודה" we eat with kiddush -- in the sukkah definitely requires making the bracha of לישב בסוכה. So when having your bread or wine, you will first make the appropriate bracha, then the bracha of לישב בסוכה, the take a bite/sip. The bracha of לישב בסוכה is not an interruption between the bracha on the food and the eating because the bracha of לישב בסוכה is a requirement for that eating event. The minhag as well is not to make the bracha of לישב בסוכה if you are just sitting and visiting or learning or even sleeping in the Sukkah. What about just a piece of cake, or a piece of cake with visiting or learning or sleeping? In that case, since there is a doubt about the requirement of making a לישב בסוכה, the halacha is to make the לישב בסוכה before the בורא מיני מזונות in order to avoid an interruption between the בורא מיני מזונות and eating.
This halacha was said by R' Fuerst, shlita, at his Sunday morning shiur. I know/we all know how serious it is to avoid any interruption between a bracha on food and eating it, so I asked why don't we just always make the לישב בסוכה first and avoid any problems. Answered the dayan: because of תדיר ושאינו תדיר תדיר קודם. That is, we make the bracha on bread/wine every time we eat, but we make לישב בסוכה only once a year and when eating in the sukkah, therefore תדיר ושאינו תדיר תדיר קודם dictates that the bracha on bread/wine will come first. Once there is a question if לישב בסוכה is required at all, perforce it would be an interruption between the bracha on bread/wine and the eating/sipping.
Hence the title of this TftD. Before this shiur, I had only seen תדיר ושאינו תדיר תדיר קודם applied in cases where it had no competition. You know, just when you have to do one thing first and you have no particular reason to choose one before the other. I had never before seen תדיר ושאינו תדיר תדיר קודם applied when there was competition with halachos that would dictate a different order.
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