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"Let's Have Deep Conversations About Life," Says This Boston Startup


Skip Small Talk
Image Credit to Carven Boursiquot, taken at Brooklyn Boulders

When I arrived at my first-ever Skip the Small Talk event at Trident Booksellers’ cafè, the small room was packed with strangers. After writing my name and pronouns on a nametag, I settled into an empty seat, anxiously awaiting my first directions. A friend had brought me to the event, describing it as “a thing where you like, talk with people”. So needless to say, I didn’t have much to go on.

Eventually, a bubbly, curly-haired woman strode to the front of the room. Quiet enveloped the crowd.

“Welcome to Skip the Small Talk,” Ashley Kirsner said. “Tonight, get ready to, well, skip the small talk.” 

Kirsner, Skip the Small Talk's founder, was inspired to found the startup by her work at Samaritans, a volunteer-run suicide hotline. She wanted to create a space where people could be comfortably open and vulnerable with one another.

Skip the Small Talk is a Boston-based startup that holds two to three hour events in which a group of complete strangers are paired up and given conversation starter cards, each labeled with a different question or prompt. Throughout the course of the night, attendees hold various conversations with one another, often about deep topics, in an attempt to “skip the small talk” and have meaningful discussions instead. Event tickets are ten dollars per person.

The event is structured so that in each conversation, one person plays the role of the speaker, and the other as the listener. The listener is instructed to simply listen, and is discouraged from replying to the speaker until after the 3-5 minute timer runs out. Then, the two switch roles. Afterwards, both attendees talk about their conversation.

Skip the Small Talk’s prompting cards can say anything from “talk about something you really like” to “what is your greatest fear?”, and as the night went on, I found myself involved in a variety of different one-on-one, and later group, conversations. One man simply talked about how much he liked sociology. Another woman vented about her tyrannic boss. In my favorite conversation of the night, a child psychologist who had recently quit her job to move across the country gave me career advice, encouraging me to pursue my passion.

“I want people to feel more comfortable getting deeper, faster,” said Ashley Kirsner, the founder of Skip the Small Talk. “Because vulnerability is the fastest road to connection.”

Ashley Kirsner Headshot
Image credit: Michael Goodman

In Kirsner's work at Samaritans, she encountered many people who felt most comfortable confiding in strangers than with those closest to them. Kirsner wondered if she could extend these short interactions into a larger event. She then hosted what she called a “skip the small talk dinner”. “I expected like ten friends to come out of pity and solidarity,” Kirsner said. “Before I knew it, we had almost 100 people say they were going”.

Now, Skip the Small Talk has hosted almost 100 events at local businesses and organizations, such as Aeronaut Brewing Company, Trident Booksellers, and Hostelling International. It also leads private events for companies and schools. Typically, there are 50-100 attendees per night.

In addition to encouraging deep communication between attendees, Skip the Small Talk aims to provide a therapeutic benefit for attendees. Based on Kirsner’s background in psychology, as well as her past research work at Boston University, the event incorporates mindfulness practices to reduce distress tolerance. “There’s a lot of research on self disclosure, and how being mindful of your feelings can help you through [distress] a lot more smoothly,” said Kirsner.

In May, Skip the Small Talk was accepted into the 2019 MassChallenge accelerator. Going forward, Kirsner plans on selling Skip the Small Talk's conversation cards, so that people can continue the deep-talking from home. She also wants to host Skip the Small Talk in the "loneliest cities in the U.S.' over the next several years. To keep up to date with both of these, Kirsner encourages signing up for Skip the Small Talk's email list.

Personally, my Skip the Small Talk experience has left me with one enduring side effect. Whenever someone tries to talk to me about the weather, I have an intense urge to interrupt them and ask, “Hey, can we talk about the meaning of life instead?”


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