Bob seems more mad that he didn't have a dream high school experience than he seems traumatized by being bullied.
That's where I was trying to land.... but kept missing.
I was upset at what happened TO ME in school, but got over it - so school wasn't the greatest, big deal, you'll spend most of your life OUT of it.
Bob's upset at what DIDN'T happen, and CAN'T get over it because his life depends on it for value - I am a respected, big-brained, superior being! AND NO ONE CAN SEE IT BUT ME!!!!
Lord knows I don't have the patience, but I'm assuming the argument is that cancel culture isn't real because something something you just have the wrong ideas so it's okay to eject you from society. That's some audacity to claim that their own free speech is being hampered because governments aren't allowing them to shut down others' free speech. Hey morons, that's not how it works. Funny how they're all for free speech until they're in power (oh wait no it isn't).
Where the cancelists make the big mistake is that they believe their opinions are truths and "common sense" whereas opposing opinions are either manifestations of mental illness and/or the "natural" hatefulness of lesser people who have not been enlightened yet or have, but reject it due to jealousy that they'll never be as smart as their betters, like Bob.
You cannot convince them they aren't being fair by censoring everyone who expresses different opinions because to them, that's as insane as saying you can't punish a child for playing with matches: bad/dangerous behavior must be disciplined out of society, and having wrong opinions is just the same as playing with fire - someone's gonna get hurt if we let it continue.
To them, making it impossible for holders of wrong opinions to express them is the same as taking away that book of matches from the child: They are merely preventing the disaster that will surely happen if wrong behavior is left unchecked.
It's a fundamental misunderstanding of what free speech
is - To them, free speech is the right to pledge loyalty to that which has already been declared correct, not literally whatever is on your mind. Much less question the ruling dogma. To a leftist, free speech/ expression is "you can have a favorite flavor of chocolate" not "you can have a favorite flavor of ice cream" because "we all know" (right side of history) that chocolate is the best and only a dunce would disagree.
Censorship to them is a VIRTUE because in their world view, every voice silenced makes us safer and happier in the long run.