When Whumpees take something down with them as they collapse: a table cloth, a chair, a mannequin, a sign or banner, an end table, another person...
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When Whumpees take something down with them as they collapse: a table cloth, a chair, a mannequin, a sign or banner, an end table, another person...

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I love it when a Whumpee is stubborn. When they know they're about to collapse. When they know they're too sick to push through. When they've been trying for hours to escape their bonds. I love it when they're staring defeat straight in the face and they spit at it and keep going. Even if it's only another step, it's the fact that they tried.
Caretaker is holding a critically injured Whumpee in their arms, frantically searching for anything in their supplies that could help. They don't have anything... except for an item that revives the dead. Caretaker either has to wait until Whumpee succumbs to their wounds to use it... or, they have to kill Whumpee themselves.
Whumpee takes a blow for another member of the team, and is scolded for their recklessness and inability to care about themselves. So the next time Whumpee sees an opportunity to jump in front of a teammate and deflect a blow... they don't take it, and are scolded for being selfish. Bonus: the teammate is permanently out of commission because of this (whether by injury or death), and Whumpee has to deal with the guilt on top of everything else. Conversely, Whumpee's so mad about nothing they do being good enough that they feel very little guilt at all, just rage and the want to blame Teammate's death on their leader.
Hero's gravely injured in a fight against Supervillain and they need to recover, somewhere out of the prying eye of the public. Somewhere secure. Somewhere private. Somewhere with a lot of technical and advanced medical equipment. Their first thought isn't a hospital, and a hospital still isn't private enough for Hero's needs, so where do they end up? At Villain's doorstep, mumbling that they had nowhere else to go. Conversely, Villain takes them in but only on the condition that Hero surrenders themselves to them, and Hero's in too bad of a state to disagree.

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A society of magic-users comes into their power at a random age, suddenly wracked by a terrible illness and pain as the once-dormant magic spreads through the body. Many are overwhelmed by the intense side effects this brings and die, and only the most resilient (or luckiest) of mages survive to embrace their new power. Whumpee is notorious for their horrible immune system and fragility, and all of their loved ones have quietly worried for the day their powers would manifest. That day has finally, unfortunately arrived.
Whumpee wistfully mentions that they've never been able to have their favorite cake, and Caretaker immediately assumes that no one's ever made it for them. They decide to fix that immediately and spend hours searching, baking, and decorating a gorgeous cake, just in time for Whumpee's birthday. Whumpee eagerly takes a giant slice once they hear it's their favorite, only to panic one they taste it. There's a reason they've never had their real favorite cake... it's because they're allergic to one of the key ingredients.
Caretaker, who's been mostly stoic throughout the entire ordeal, finally breaks down begging and pleading for Whumpee to wake up as they're lowering Whumpee's coffin.