New App Tells All Your Friends When You’re Free to Hang Out

Danny Trinh calls it the “blinking cursor” problem. It’s Friday night, you don’t have plans, and you’re wondering who to text. There are a handful of close friends you can shamelessly spam, but beyond that, things are more complicated. Should you message that new friend from work, even though they said they were busy the last two times you tried? Is it weird to hit up that one sort-of-friend from college? Some will dismiss these as trivial concerns; others will know exactly what Trinh’s talking about. “At the acquaintance level, it can be really stressful,” Trinh says of making plans. “You’re spending social capital to ask them to hang out.”

Free is Trinh’s attempt to solve the blinking-cursor problem. The iPhone app is meant to fill what the designer sees as a small but critical hole in our digitally mediated social lives: the ability to broadcast and communicate around availability. It makes hang-out intentions a little more visible in both directions: You can see if friends (or acquaintances!) are doing something, or looking for something to do, and vice versa. Trinh has another way of explaining it that folks of his generation—millennials—are sure to understand: He wants to build the modern, mobile version of the green dot from AIM.

Trinh, 24, was formerly the lead designer at Path, the inner-circle social app that couldn’t ever quite convert interesting ideas into mainstream success, and he thought about AIM a lot in the course of developing Free. (One of his investors is Chamath Palihapitiya, who ran AIM in the mid-aughts.) Looking at the diverse tools we use for communicating and connecting today, Trinh sees much that can be traced back to AOL’s seminal chat program. “The AIM buddy list is the godfather of all social software,” he says, and he might have a point. Even before texting, it was AIM that got an entire generation hooked on chat. Those status updates that Facebook and Twitter are built around? Offshoots of the once-ubiquitous away message, Trinh says.

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What Trinh thinks is missing is a way to advertise our availability, and quickly survey the availability of others. “I used to live on AIM, and if someone was green, that meant they were totally up to chat. I was in love with that,” he says. With smartphones, we’re more connected than ever—there’s Gchat, WeChat, Snapchat, Facebook Messenger, and more—but as connection has become the default, we’ve lost ways to announce, “I’m up to hang.” “In a world where everyone’s online all the time, what’s the true availability signal on top of that?” Trinh asks. “That’s what we’re trying to build.” Put another way, now that we carry chat on us at all times, the green dot is assumed. Trinh thinks there’s value in making it explicit.

Doing so proved a delicate challenge. Trinh and co-founder Kelvin Kakugawa built five or six distinct versions of Free in the course of its development over the last year and a half. The first one was just a button that said, “I’m available.” But test users were reluctant to push it. It revealed an important insight that gets to the heart of the problem: No one wants to look desperate for something to do.

With the final version of Free, released last week, users can broadcast one of three statuses: Going Out, Flexible, or Busy. At a glance, you can see what the “going out” folks are doing and jump into a chat session around those hangouts. As opposed to, say, seeing someone check into a restaurant on Foursquare, seeing a “going out” status on Free comes with an implied opening to invite yourself. Trinh and company have called it a “Horn of Gondor” for friends.

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On the other side of things, there’s the flexible status. It means what it says, but it’s also an option for people who actively are looking for something to do. It solves the desperation problem with a deft bit of ambiguity.

Of course, not everyone frets about “social capital” and the optics of asking acquaintances to hang out. There are folks who will fire off a Facebook friend request to the person they just chatted up at a party, because that’s what Facebook is for, what could possibly be weird about that? But there are also those who agonize over the protocol for sending Facebook friend requests, or avoid the problem entirely by leaving the friend requesting to others. Whether the pitfalls are real or imagined, relationships can be fraught, and technology can certainly bring new dimensions to these age-old anxieties. With Free, Trinh is hoping it might help us alleviate them, too.

Social neuroses aside, Free represents an understanding that “communication” and “connection” aren’t just big monolithic problems that are solved automatically when you give everyone a smartphone. Human interaction is a nuanced and complicated thing, and we could benefit from tools that reflect this complexity. Sure, we could go on coordinating our social lives by text message—it isn’t that bad. But we could’ve gone on sharing photos via text message, too, and that didn’t stop Instagram from catching on. Maybe there really is a better way to hang out. I talked to Trinh the morning after the Golden State Warriors won the NBA Finals, and he said Game 6 had served as a satisfying proof of concept. “There were six different places I could’ve gone to watch the Warriors,” he says, having seen friends hanging out various places on Free. “I wouldn’t have known about any of them otherwise. That’s pretty amazing.”

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Trinh acknowledges that hang-out logistics might seem like a provincial concern, and in a way, they are. Free is very much tailored for young people with busy social lives in big cities. There are surely more pressing problems to solve. Still, in a world where so many so-called social apps yield a bunch of people by themselves, staring into screens, it’s hard to hate on anyone trying to bring people together in the actual, physical sense.

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