I think about this a lot.
Are you scrubbing? Are you too cautious? If you're scrubbing, and not just making a mistake, it means you are putting on an act and out of your depth. Are you too cautious? You aren't playing to your potential.
Are you too nerdy or too bro? If you're too nerdy, you aren't acting fast enough on what you know, so you aren't being real with yourself. If you're too bro, you aren't checking the facts and you're stumbling over those who know better.
Are you too greasy or dry? If you're too greasy, you're sliming your way into things you are neither qualified nor a good fit for. You can easily end up with the wrong person (or, say, job) before you both realize you don't actually like each other. If you're too dry, you're getting caught up on things that don't matter relative to what you could be doing. Too dry and you won't get the job or find the person(s) you match up with.
Are you thinking in pure tropes or are you thinking in only the literal words?
My quest is to learn my ever-adjusting limits, my level of cool, and do my best. And that takes being genuine, which takes learning and practicing.
I think that it's also important to intuit someone's boundaries early on and not impact them with being more open than they want or can handle, but otherwise just be raw and honest.
The downside: Sometimes, though, people are so busy reading between the lines or listening for ulterior motives that when you're honest, they think you mean something other than what you said and take offense. Like, take offense at something they completely imagined. I found in-person people have occasionally begun taking offense at things I never said nor intended nor suggested ever since I've been speaking much more plainly and directly this past year.
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A side anecdote, last year just back from Burning Man where you get a real intense experience of what's real (much of it) and what's fake (some of it) and what's pretending/playing but in an authentic way (a lot). I was in a bar in Oakland and this dude wearing a hat was annoyed I found his friend a more interesting rando conversant, because this guy was more outgoing etc and wanted attention, and the friend was chillin' and didn't. Anyway, the dude interjects about my hair loss (lol really man?) and I forget what he said but I was like, pretty unperturbed at the time and then asked him why he was wearing a hat. Turned out he had a few grays in his 30s.
Eventually, I was just pretty blunt, "you just gotta love yourself".
He tries to get me on being a hippy, which is a compliment when you think about it, but he dodges over to "I mean, I think I'm pretty awesome" like that could be the same.
I don't really know how to describe it better, but I felt that was the core of how he wasn't fully honest with himself. Seemingly subtle shifts to avoid the painful truth, that he didn't actually like himself. The guy was blunt and open and didn't outwardly lie as far as I witnessed, but he wasn't full real. And he hurt.