What makes this difficult to get across is that there are relationships I have where I'd almost agree with you. There are people I'm friends with where we have,

What makes this difficult to get across is that there are relationships I have where I'd almost agree with you. There are people I'm friends with where we have, for lack of a better word, 'contracts' where we've promised to never lie to each other, even about trivial things and even if it's hurtful. But in the same way that there are gradients of anxiety, there are also gradients of friendship. I do not need to be comfortable having difficult conversations with my coworkers. I can have difficult conversations with my coworkers if it's important, but there is no inherent virtue in forcing myself to go through that unpleasantness just so we can plan a board-game night. Your view also discounts the extent that relationships develop over time. You do understand that immediate, radical honesty isn't how relationships work: > Well yeah, if you lead in with that, that's pretty intense. But you don't follow through with that thought to its natural conclusion. If I'm not going to lead with something like this, what you're essentially saying to me is, "you should be uncomfortable around our calendar until I feel comfortable having this conversation with you." My understanding of your position is that if I don't force myself to feel safe talking about small things, I won't ever feel safe talking about big things. Frankly, I don't think that's a realistic or practical view of relationships, and I guarantee if you applied that standard equally to all of the other social graces you extend to everyone around you, you would not have many friends (deep or otherwise). I disagree that accommodating some behaviors necessarily means that relationships can't deepen over time. Of course practicing vulnerability is important for relationships, but it is equally important to practice grace and care. If you show people you care about making them feel safe rather than pressing every issue, then they might eventually feel safe enough to trust you to be gentle when they're really insecure about something serious. I've mentioned this elsewhere, but I deal with people who will get incredibly lonely or feel incredibly disliked if they're left alone for a long period of time. I'm curious, if I built a calendar app for my friends that reminded us every 3 or 4 days to call that person and catch up with them, would you say that's an unhealthy technological solution that's stunting the relationship? My take on this kind of 'dishonesty' is that sometimes friends agree to handle each other's quirks and work around their specific issues rather than barreling through them head-on, and that doesn't mean they're avoiding responsibility or undermining the friendship. It just means they care about each other and want to meet each other's personalities halfway. > Tolerating things is not the same as leaning into them so hard that you build an app around them. I don't want to get too off-topic or dismissive, but I think this is a somewhat uncritical view of how modern relationships work among most 'normal' friends. We've built Tinder and designed blind dating apps to help people get around their social anxiety asking strangers for dates. People go to bars and drink substances designed specifically to bypass the restraint parts of their brain so they'll be less guarded with their friends. We've built apps like Facetime so that people who lack the ability to emotionally connect to written messages can get the visual and auditory signifiers they need to feel connected to other people. We build games that are designed to let people avoid boredom. We use online polls among friends to avoid conflicts around small decisions. We build bar-room trivia apps for people who have problems interacting with each other or picking conversation topics without 3rd-party intervention. I pretty regularly go out of my way to build systems, use systems, and structure my life to accommodate behaviors that do not make sense to me, and I still manage to avoid thinking that every person with those behaviors is broken and needs to be fixed.