The saddest food should be emergency rations. The end of humankind is inevitable. It might be an epidemic, a meteor strike, nuclear war or something else. It doesn't matter. The last thing the last human on earth will eat will be some kind of long-lasting high-energy survival bar. That last human survivor will eat the bar while thinking: "Why am I eating this? Why am I still trying to live on? It will only prolong my loneliness..."
The saddest food is bad cake. You start eating it thinking that while it's unhealthy at least you will enjoy it, but no, you won't enjoy it because it's bad. From the first bite until the last you are stuck eating this unsatisfying (possibly offensive-tasting) cake that is bad for you and will mean you have to do without something else unhealthy but more satisfying.
Then, as you approach the end, you think, well at least finishing this thing will be cathartic. It's not, though, and then you start doubting whether you really did need to finish it if you hated it so much.
The saddest food is planning on having microwave popcorn for dinner, only to realize that your roommate has just moved out without warning and now you have no microwave.
Every time I go out to eat there's always a table where no one is talking. Sometimes it's a mother ignoring her child. Sometimes it's a couple in their mid 50's that has nothing left to talk about. Sometimes it's a painfully awkward blind date. But it's just two people there silently staring at each other until the food shows up.
The saddest food is any kind of poorly prepared meat, because something literally gave its life to produce it. That chicken or cow could have been turned into something delicious and wonderful, and yet all that it has to show for its death is a grey, flavourless or overproduced lump of food. The first time I remember feeling this was when I was in America and went to a Popeye's Chicken franchise.
Anything that comes flavored with guilt and disappointment is the saddest food. If you are on a special diet, for health/religious/personal reasons (vegetarian, kosher, celiac, etc), and friends or family cook for you, going out of your way to make you a special item to eat, only it's something that's outright bad, not even half-assed, features a main ingredient you dislike, or is way overdone when you'd have been happy with something the rest of the family is eating, just hold the [cheese/meat/bread]. They took the trouble to meet your needs, and you appreciate the effort, but the result was bad, and there's no possible way you can bring this up without looking and feeling like a tremendous ass. That's a sad meal right there.
The valor pigs have been looking over your uniform and trying to find fault. Time to show them how army is done!
Video games make it socially acceptable to point at Jane
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