> > 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."

No, I'm saying that your uncomfortable-ness around this is irrational until you see some reason to believe the person will lie to you, and if you're close enough to recognize that someone is lying about wanting to hang out, then you're close enough to have that conversation.

Making this about concern for other people is just a foil to avoid looking at yourself. This isn't about them: it's about your social anxiety, not theirs.

> 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?

No. I think that's a great way for you to deal with forgetfulness to achieve a kind goal.

The problem isn't technical solutions. The problem is that this technical solution doesn't solve the real problem, which is solvable, and instead enables it.

> 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.

Again, "normal" isn't my goal.

> We've built Tinder and designed blind dating apps to help people get around their social anxiety asking strangers for dates.

And while that has worked out for some people, I think you'd have a hard time arguing that it has actually empowered people to ask strangers for dates, or more importantly, to create meaningful connections.

> 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.

And while that works for some people, I think you'd have a hard time arguing that it actually results in positive, deep relationships. While deep relationships might involve some alcohol, the reasons they are deep aren't based in drinking together from my experience.

> 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.

Yes, and that helps bridge the gap when face to face interactions are not possible--I'd view this as a positive thing. But it also can't fully close the gap with relationships where touch is important.

> We use online polls among friends to avoid conflicts around small decisions.

Do we? I've never even seen this, and probably just wouldn't respond if a friend spammed me with a link to some poll site. If people do this, I'm pretty sure it would be ineffective for that goal.

> We build bar-room trivia apps for people who have problems interacting with each other or picking conversation topics without 3rd-party intervention.

Trivia games are a way more complicated topic that fulfills a lot of human needs. I don't think (after doing a lot of work) that I have a hard time interacting or picking conversations, but I'd still be down for trivia for a lot of reasons unrelated to this.

I'm going to reiterate that a lot of the things you're attributing as solutions to social anxiety, would be better addressed by actually seeking help for social anxiety.