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Ask Your Most Sensitive Questions

Two sex educators made an app with the answers.

OkaySo - Expert Life Advice

For Relationships & Sexuality

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In 2012, two longtime sex educators getting their master’s degrees at Columbia University had the idea to create an app where users could anonymously ask anything—yes, anything—about sex, dating, and relationships. The kind of stuff you’re too nervous to ask a friend. Experts in their fields would privately answer these questions, which could be about anything from HIV/AIDS to gender identity. And Okayso was born.

“People tell us that being able to ask questions anonymously allows them to say things they otherwise wouldn’t,” explains cofounder Elise Schuster. “They can really let out the stuff that’s the deepest down inside them. And that gives us the chance to help them see they can move on.”

This year, the app was revamped with what Schuster calls a “warmer, more welcoming” look and the ability to see previously answered questions. Okayso also started partnering with nonprofits like the The Advocates and the Georgia Campaign for Adolescent Power & Potential to directly connect users to more resources.

Cofounder Elise Schuster

OK, so how did Schuster make this happen? Eight years ago, she and her now-departed cofounder received an Obama administration Teen Pregnancy Prevention Program grant to build a prototype of Okayso. Another $300,000 in funding came in 2016 to launch the nonprofit app, which relies on teams of volunteer experts to answer your questions.

“We ask volunteers to do 15 minutes a day,” Schuster says. “While you’re waiting for coffee or the subway, instead of just doing nothing on your phone, you can pull it out and help someone really quickly.”

Users are on average 18 to 19 years old, but range from a high school senior wondering if she should dump her boyfriend to a 50-year-old navigating his wife’s menopause. Qualified experts include medical doctors and experts from partner nonprofits.

The app’s experts are friendly and approachable.

If your question is a genuine emergency, Okayso’s experts will get as much information as you’re willing to share, then direct you to appropriate resources. The app defines “emergency” as issues related to your immediate health and safety, such as child abuse or thoughts of suicide. However, this has not stopped users from writing in with questions like “EMERGENCY! I have a date in a few hours. How do I...”

And, yes, Okayso does give advice on sexual topics, which mostly focus on figuring out what’s right for you. Because of the level of attention the app provides, Okayso is growing slowly to maintain its quality: The ratio of users to experts is currently about 100 to 1, and most people receive a response within a few hours.

My partner has HIV. How can I stay safe?

When COVID-19 hit in the spring, Okayso quickly assembled a dedicated response team. But they found pandemic-related questions were coming up across different fields of expertise.

“Folks had questions about being trapped with someone in quarantine and not getting along, so that ended up in our dating-and-relationship team,” Schuster says. “People weren’t sure if they should go to the doctor’s office for their annual checkup, but they needed their birth control refilled, so that went to our birth-control team. We’re seeing COVID all over the app.”

Also new this year: Other users’ questions and answers on the home page. Those observing World AIDS Day might be interested in questions like, “When is the best time to get tested for HIV if I think I might have been exposed?” and “My partner has HIV. How can I stay safe?”

Reading other people’s questions can be enlightening, even if they’re not directly relevant to you. Schuster recalls one in particular: “My girlfriend and I are going hiking in the woods to look for waterfalls,” a young man wrote. “We have been together for two years. Do you think that tomorrow would be a good time for us to see each other naked?”

“I really appreciate that this person is trying to figure out whether they should move on to a next step of intimacy and be more vulnerable with each other,” Schuster says. “That type of question is something we get all the time, though in front of a waterfall is not as common.”