Sometimes, it's hard to tell when people are being sincere.
Sure, Conan O'Brien made a good point about cynicism, and there's truth to it. I'm not innocent on that count.
But it's not just that. I received good advice about job interviews, once, and it was that you can't really tell how it went based on how your interviewer acted. Maybe you bombed, and your interviewer is a really nice person who felt bad for you. Maybe they thought you were perfect, and are giving you a hard time to make sure you won't get flustered under pressure.
They're humoring you. They're testing you. You don't know how you're actually doing.
Now apply that to all social engagements, ever. I'm not even on the spectrum, but if someone is super-nice to me and then says crap about the people they love the most, I don't know if they like me at all! Frankly, it's why I had so few female friends in high school and college -- in my limited experience, girls were more likely to play that game than boys were (boys played other games, and I've lost patience for those, too, but the nice thing about being an adult is you can choose friends who only play the games you like. I'm a fan of Cards Against Humanity, myself).
Then you add in the tendency to make jokes to cope, or to snark when you care. If you see a movie with two people, and Person A goes on about how great you are at picking movies, because that's how you play the game, while Person B nitpicks everything that went wrong, because they value the franchise so much, then how are you supposed to know that Person A hated the movie while Person B is going to go out and see it three more times this week? Are you even supposed to know?
Add in self-esteem issues that, let's face it, most of us have. I'll walk down the street and some jackass makes a sexist comment. And, honestly? I don't think, "Rape culture, that guy thinks he's entitled to my body." And I don't think, "How nice, a stranger thinks I'm attractive." I think, "Oh, he's hitting on the ugly girl to make his friends laugh." Yep, I assume he's making fun of me. So going back to the movie scenario? I read the pleasant game-playing and the tender snark, both, as "We both hated the movie, so our evening was ruined, and since you suggested the movie, it's all your fault."
All this adds up to never being quite sure I'm being taken seriously. If I say, "Hey, I liked the movie," am I playing the game? Honing my deadpan snark? Enjoying the movie in a hipster-ironic way? Or do I actually, sincerely, like the movie?
If I say, "This needs to be fixed," do I mean "Huh. This is a fact,"? Do I mean, "Hm, I need to put this on my to-do list,"? Or do I mean, "Hey, you need to get on that,"? Because if I say, flat out, "You need to fix this," isn't that nagging?
I'm not going to pretend every word out of my mouth is sincere. But I do want to be taken seriously. And, on the off chance I already am taken seriously, I want to be able to see, hear, know that.
I suppose that's a lot to ask.