So why in the world is there בדיעבד? We are already doing so much as frum Jews. Just give a single, uniform standard, and we'll perform to task (or not). The truth is, this question was already addressed by the Chovos HaLevavos. Here is the executive summary: There are three categories mitzvos: עשה/positive/you must do; לאו/negative/you are forbidden to do; רשות/permitted/optional. Examples would be making kiddush Friday night is a positive mitzvah, eating pork is a negative mitzvah, wearing tzitzis is optional -- kosher slaughter is optional; if you want meat, you have to slaughter it a certain way.
Says the Chovos HaLevavos -- that's a mistake. There is always a singe best thing to do (or not do; which is also doing). The רשות mitzvos are not really optional; they depend on the situation. Sometimes you are in a tight spot and you need to navigate between the רשות to accomplish the עשה and avoid the לאו.
Would an example help? Sure. Imagine being in the middle of nowhere. (By nowhere, I mean that even Chabad is further than the nearest Walmart.) You have 8 oz of grape juice, two rolls, two slices of bread, and and some Diet Coke. Shabbos just started. Now what? Rule One -- Don't panic, just assess the situation.
First, you have an obligation of three meals, each of which -- לכתחילה -- require two complete rolls of bread. That means, at a minimum, four rolls -- Two at the first meal, where you eat one and save the other. Two (one from the first meal) at the second meal, eat one and save the other. Then the third meal. You only have two rolls. You are out of לכתחילה land.
Second: you have kiddush Friday night, kiddush Saturday morning, and havdalah Saturday night. You need 4.2 oz Friday night (since Friday night kiddush is a Torah obligation), 3.3 oz on Saturday morning, 3.3 oz for havdalah. That adds up to 10.8 oz. You are out of לכתחילה land.
Now what? Here's the rule: In a hour of distress/שעת הדחק, then בדיעבד becomes לכתחילה. There is a fair amount to play with now. The third meal doesn't require bread if you don't have any, but that's very בדיעבד. Some say you can make kiddush Friday night on bread, but that's very בדיעבד. You can use a national drink/חמר מדינה for havdalah and kiddush, but that's very בדיעבד.
Here's what I poskened (and later verified was the best option, given the circumstances): Friday night, pour 4.2 oz of grape juice for kiddush and use two rolls. Drink just a cheekful of the grape juice, then pour some more juice into the cup (to take of the stigma/פגם of having been sipped, and then pour the contents of the cup back into the bottle; save for later. Eat one of the rolls; save second for later. Saturday morning -- pour at least 3.3 oz of grape juice, but only drink a cheekful. Then same drill to remove the stigma/פגם then back into the bottle. Take a roll from last night along with one slice of bread -- to still have לחם משנה. Eat the roll. Third meal is made on two slices of bread. For havdalah, finish the grape juice. Note: We needed at least 3.3 oz of grape juice for havdalah to have enough over which to make the final blessing/ברכה אחרונה on grape juice. The other two meals you had bentching, so you were covered.
That's why we learn בדיעבד's. Not because, "meh.... בדיעבד it's ok". Rather because we need those to navigate the hours of distress in our lives. One more thing: I got this question about an hour before Shabbos... obviously there was no time to start looking things up nor even find a rav... and I thought all those בדיעבד's I was learning were all just for the sake of learning. HaShem showed me; again.
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