A criticism I've seen of Charlie since the middle of Season Two is that she's incapable of really helping sinners because she can't understand what they go through due to her privileged background. I....don't exactly AGREE, but I think that does hit on a REAL issue Charlie has when it comes to reaching out to or connecting with sinners:
She isnt willing to use to her negative emotions to connect with them. Only her positive emotions.
What I mean is, Charlie is unwilling to share any of her pain, her flaws, or any of the personal suffering she's went through in life and only tries to appeal to people through kindness and happiness. But that makes others unwilling to share their real feelings with her because it comes off as her being shallow and not having any "real" problems.
There are two perfect examples of this in the show itself:
In both these instances, Charlie is SUPPOSED to be letting out a REAL part of herself to the group. And in both instances, she gives a superficial, shallow answer. Not because she doesn't have something more deep to GIVE, we KNOW she does. But because she doesn't want to give the impression she doesn't have a handle on herself, she sticks to an easy non-personal answer. Now, admittedly, with the trust falls, MOST of the answers weren't actually something vulnerable, but since Charlie is the one running the hotel, you think she'd want to lead by example. But she can't here. Because deep down, she's SCARED of actually opening up to her friends. Doesn't want to drop her negative emotions on them. Same with the venting circle. She could CHOOSE to vent about the deaths of Razzle or her mom not calling her. But she ISN'T. Because she doesn't want to expose herself like that.
And I'm sure, to her, that seems smart. Act like everything is okay, and people will think you can help them....but its the opposite. Instead she comes off to people as shallow. As not having "real problems." After all, if the worst she has to vent about is a Koala at the zoo, how can she help someone with REAL issues both in life AND death?
And some might say "But Charlie CAN'T understand things Sinners go through because she isn't one." And...No. She CAN'T. But she can understand the major emotions they all feel. She can understand failure.
Understand feeling helpless and powerless.
Understand having regrets
Understand feeling alone in Hell
And most all, understand the pain the extermiantions cause and how terrible it feels to be unable to do anything about them:
To paraphrase @aspoonofsugar , Yes, Charlie can't understand the Microcosm of a sinners pain (Drug addiction, death, gambling addiction, their soul being owned etc) but she can understand the Macrocosm of emotions all sinners feel (Shame, regret, self loathing, guilt, anger at other) and she COULD connect with them THAT way.
But she doesnt. And thats partially just because she doesn't fully grasp how negative emotions CAN connect people. Just look at Vox. Yes, he used Sinners anger and sadness at the exterminations to nearly cause a war....but he DID manage to make a large number of sinners start working together and connecting over their pain and loss over the extermiantions. And Charlie isn't incapable of that. She clearly feels a ton of pain and anguish over them. But she'd never express that publicly out of fear of seeming....not WEAK, but....incapable. Like, during her interview while she talks about the exterminations being bad and makes a mention of how much it hurts to see it comes off a bit like a celebrity talking about a disaster they were running a charity fore. They "care" but don't really "care." And thats because she's trying to....present herself a certain way to the public. And then her trying to act all excited and bubbly about her hotel just gives the impression she's kinda airheaded or isnt THAT serious. When we KNOW she cares. THIS is how she was in her last scene
Morose. Heartbroken. Looking like she desperately needs a cigarette to take a long hit off after EVERYTHING she just witnessed. That's something im sure EVERY sinner could connect with feeling. Imagine if THAT'S how she came to news station and gave her speech. Just let out all the raw emotion she had inside during her talk about the hotel. Sure, people might still see it as crazy, but its less "Ha-ha, the princess is delusional" to "Ouch, the princess is....really desperate to try, huh?" Maybe it'd even get her SOME support. But she wouldn't do that because Charlie doesn't UNDERSTAND how negative feelings can help connect people.
If someone told her "someone else feels lonely and you should talk to them about how you used to feel lonely", she might question why. She'd think that would only make them feel worse and she should just try to make them feel less lonely. Charlie needs to understand that showing or telling others you experience the same negative emotions as them, even if not in the same way as them, can make them not only feel better but see you as someone they can talk to about things because they KNOW you experienced similar feelings. People don't need to go through the same things to have felt similar emotions. But Charlie ONLY tries reaching out to or connecting with sinners using positive emotions instead of the more negative ones that both sides can more relate to.
Something i mentioned in chats, once again with @aspoonofsugar , is that deep down, both Charlie and the sinners are unhappy with themselves. Just in different ways. And Charlie can connect better to sinners if she becomes willing to admit that. Because just as Vox tapped into Sinners pain to make them lash out, Charlie can tap into their pain to help them heal. But ONLY if she taps into her own pain and admits it to THEM. After all, who wants to be told to "share" by someone who wont share herself? She has to present herself more to the sinners of Hell, not as The Princess, not as an authority figure or just someone trying to help put a smile on their face. But as the sad, scarred, starved for affection person who can understand some of their sadness. As Charlie Morningstar.