The latest anonymous chatting app is both harrowing and intriguing

My first conversation on Kindly – a new, anonymous chatting app where strangers can seek emotional support — didn’t go so well. I volunteered to be a listener and I was matched with a teenager from the United States. He or she (gender wasn’t revealed) told me their aunt — who they live with — was making sexual advances. “If I please her do you think she will let go of me?” The person asked me.

I stared at my phone slack-jawed. How to respond to a question like that? I’m not a therapist and I certainly don’t have professional training. It was possible the stranger I was chatting with was lying, spinning an elaborate ruse for fun, but I had no way of knowing. If their predicament was real, I was in no position to offer advice. It was the most memorable and worrisome experience I’ve had yet with a new social media application.

This is the foregone conclusion of anonymity meets messaging: We’re turning to strangers for emotional support, and they may or may not be able to help.

On Kindly, users can request a chat with someone else, to discuss whatever they’re dealing with. You’re guided through the request form, where you write a short summary of what you want to talk about and determine which category it fits in – anything ranging from work/business, marriage/divorce, LGBTQ issues or creativity/inspiration. You can also volunteer to be a listener by telling the app you’re free to chat.

It’s sort of like Chatroulette, if man parts were swapped out for mental anguish and you texted instead of talking over video. With its one-to-one element, it differs from Secret or Whisper, which both focus on broadcasting your thoughts to the world. Whisper has a messaging feature built in, but it isn’t the point of the app. Kindly is a bit more like YC grad 7 Cups of Tea, although the “listeners” don’t purport to be trained and Kindly is mobile-first, making it easier to use on the go. 7 Cups of Tea hasn’t released a mobile app yet.

Both Kindly and its 7 Cups of Tea competitor are built on a fascinating concept with so much to dig into from a social-psychological perspective. It’s crowdsourced emotional support via a digitized network of strangers. It isn’t new, of course. Forums and chat groups have existed for ages around particular problems or topics. But by introducing the one-to-one messaging element, rolling it into mobile, and making the topic of conversation open-ended, Kindly is attempting to scale it to the masses. When you’re lying in bed feeling lonely and in need of a friend, it’s the app for that. Depressing to relegate it to strangers? Perhaps. In the Facebook-Twitter age we’re used to getting our social hits via the safety of a screen.

But as my first chatting experience shows, Kindly is fraught with peril as much as promise. Since it’s framed around conversations about self-betterment, people are far more likely to discuss the challenging issues they face than they would in say, Chatroulette, or a public chat room. And, as I encountered, users may look for advice on sensitive issues from unvetted strangers. It’s a similar issue faced by Australian app Moodswing.

Let’s say someone’s trying to decide whether they should tell their parents they’re gay – a stranger from a different cultural, geographical, or religious background is not the best one to offer recommendations. What if someone is feeling suicidal, and they get matched with a Kindly listener who is busy at work and doesn’t respond? The potential “oh no” scenarios are endless.

Founder Jordan Walker is well aware of the pitfalls of his creation. “I’m admitting it, we’re a team of two people in the MVP (minimum viable product) stage,” he told me. He hasn’t even raised his seed round yet.

He’s gathering a board of therapists to serve as advisors to the project and wants to compile resource recommendations for listeners to consult if they’re out of their depth. He’s also hiring a community manager as his third staffer to gain insight into how people are using the app.

Walker will struggle to build Kindly’s network to a self-sustaining size. I tried requesting listeners and volunteering to be a listener several times over the course of a few weeks, to no avail. There’s clearly not enough people on the app to make supply and demand equal in real time. And this isn’t the sort of app with a built-in viral quotient. Who’s going to want to share with the world that they’re using an emotional support chat tool?

Kindly is in the earliest stages of its creation – the app is buggy and unreliable, the network small. But it’s tackling the need for human connection in a novel way. Walker is a first time founder after previously working at Spotify, so he’s winging it. But I’ll give him credit where it’s due: He’s built a social application unique enough to intrigue this social media beat reporter.