Okay it's time for me to rant about Digimon again because. Because. I want to talk about this-
These two clowns (affectionate) tried to fight giant monsters with their bare hands. Which is how they ended up getting strangled. Tai thought it was a good idea to poke Shellmon. With no sense of critical thinking, he decided it was the best idea. Matt was trying to save TK, with no regard to his own safety. He could die right there and who cares, right?
I'd argue these two were actually at their worst when the digivolution occurred.
Tai: Reckless idiot moron, angers monster with unga bunga tactics, could have put the rest of the group at risk if he and Agumon didn't sneak a snack earlier
Matt: Also reckless idiot moron, puts TK's safety above his own life, was perfectly ready to die for his brother, sees himself as disposable as long as TK is safe
Not only is this a perfect example of their flaws, but this behavior also leads directly into both SkullGreymon and Matt's fall to Cherrymon.
With SkullGreymon, I feel like Tai wasn't just taking known data (partner in danger, Digimon must be fed, etc.) and executing it at random. I feel like he was trying to recreate the events that led to Greymon. Other than feeding Agumon too much, what does he do? He runs up to the giant monster and yells at it.
In desperation, Tai does what he knows has worked in the past. He's willing to face certain death trying to unlock the Ultimate level. By now, he understands that digivolution helps protect the group, and he's putting all the weight on his shoulders.
But the crests rely on personal growth to work. Tai isn't growing. He's not ready. He's lost and confused and doesn't know anything except he's the only one with a crest. Result? SkullGreymon.
Matt had plenty of stupid moments similar to this (i.e.- putting all the weight on himself and throwing himself into danger, though he's more focused on TK only rather than the whole group). I think the reason most of those moments didn't result in dark digivolution is because Matt is more introspective. He's more likely to ruminate over something for a million years instead of taking action. Which leads me to Cherrymon.
Cherrymon plays with Matt's insecurities. He's already worried that TK is spending more time with Tai (and the rest of the group, though Cherrymon focuses it on just Tai). TK's recent victory in Puppetmon's gun game proves he can protect himself. Between this and his growing connections to others, Matt feels useless. He's made his entire existence about protecting TK- the very thing that created Gaurumon to start with.
I always wondered why there was never a dark digivolution after this. Because I am a fucking nerd, I did some research and BlackMetalGarurumon wasn't actually released yet. It was on a card that would come out three months after this episode aired. So let me introduce to you-
SkullMammothmon digivolves from WereGarurumon, existed when this episode aired, and is a "skull" Digimon as a nice thematic bonus. Imagine if Matt came riding back to the group on this big guy! The SkullGreymon parallels! The Tai and Matt parallels! The wasted potential!
I love how Tai and Matt are both idiots who would readily give up their lives to protect others. But they're also so different. Tai does stupid things for the sake of the entire group. Matt does stupid things because he sits on his personal issues too long. Tai does the first thing that comes to his head, whether or not it's actually a good idea. Matt will suffer from behind-the-scenes angst and not tell anyone ever. Unlocking Greymon/Garurumon stems from their issues, just as they unlocked the Ultimate level through their strengths.
