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Feeling weird about socializing? Skip the Small Talk wants to help

Ashley Kirsner’s social nights help people build community — and learn to talk to strangers again

Ashley Kirsner, founder of Skip the Small Talk, leads one of the socializing events at Trident Booksellers & Cafe. Kirsner, who has studied social psychology, says many believe they need to polish their conversational skills after two years disrupted by pandemic isolation.Josh Reynolds for The Boston Globe

Love Letters

It used to be easier. At least it seemed that way, for some.

But these days, socializing with other humans can be extra awkward. It can make a person second-guess how they present themselves, and whether they’ve talked too much or not enough.

That’s why Ashley Kirsner’s Skip the Small Talk program feels different than it used to, at least to her.

Kirsner, 32, who has a background in social and clinical psychology research at Cornell, Boston University, and Harvard, started Skip the Small Talk six years ago to help people build community with strangers.

“It was born out of some time I spent volunteering at a suicide hot line,” she said. “Very rarely was the problem that people didn’t have friends. Much more often, people didn’t feel comfortable having real conversations with those people.”


Kirsner wondered, “What would it be like if we got everyone who called in to the suicide hot line, in one event — and also a bunch of people who probably have similar feelings?”

“So I hosted an event sort of on a whim. All I did was post on Facebook, ‘Hey, I’m doing this event. I’m calling it the Skip the Small Talk dinner.’” She hosted the gathering at John F. Kennedy Park in Cambridge.

About 50 people came, and Kirsner led them through a discussion of deep questions. Stuff that might be easier to confess to a stranger than a family member. Questions that also might help two people form a bond in ways they wouldn’t if they met at a party and talked about the weather.

She thought the group would stay for a few hours. “I had to kick them out after seven hours,” she said. “I had people come up to me and say like, ‘Hey, so when’s the next one?’”


Kirsner started organizing more events, first around Boston, and then in other cities. By 2019, events were being held weekly, often at Trident Booksellers & Cafe and Aeronaut Brewing Company, and in New York City.

At the two-hour events, participants were paired off with one person at a time, usually about six over the event, sort of like speed dating. Kirsner led the room by giving them question prompts. In what ways are you different from the person you were five years ago and in what ways are you the same? What’s something you’ve learned from a past friendship or romantic relationship that’s stuck with you? Describe yourself through the eyes of someone who loves you. What are some open questions in your life right now? How are you going about answering them or coping with having them unanswered?

In 2020, the events stopped because of COVID-19 and then went on Zoom, but after vaccinations in 2021, Kirsner began hosting them in person again.

It was different this time around. Some of the questions felt bigger — more important. Maybe easier to answer for some and harder for others. There was a new gratitude for having these kinds of conversations at all.

There were also COVID-related challenges. People wore masks as soon as the Delta variant showed up, and after receiving some complaints about sound, Kirsner put up poster board between pairs of seats.

After more than a year out of their routines, some of it in insolation, her audience wanted to connect more than ever.


The researcher in Kirsner is fascinated. She notices trends in her participants’ needs and adjusts accordingly.

Rich Lee of Somerville and Ginger Ramirez of Brookline during a Skip the Small Talk socializing event held at Trident Booksellers & Cafe in April. Josh Reynolds for The Boston Globe

One lesson she’s learned is that in a masked social setting, people can assume the worst of strangers’ impressions of them. Some would tell Kirsner at the end of an event that they felt rejected. Now she cautions everyone not to jump to conclusions.

Another trend? Lots of people think they’re bad at socializing after the last two years, but they’re not — at least not from Kirsner’s perspective.

“I get to tell people like hey, your anxiety is, statistically, very likely lying to you. It’s normal to feel it, but it’s not necessarily accurate.”

Both lessons, she said, people can apply to other parts of their lives.

Kirsner’s post-2020 events have been popular enough that she has expanded to Chicago, Kansas City, San Francisco, Los Angeles, and Portland, Ore, with Baltimore and Philadelphia coming soon. Trained facilitators lead the nights in each city.

In Boston, participants include people looking to re-socialize, and many who never had the chance to build community when they started a new phase of their life here.

Jacob Baker of Hudson and Christina Blakely of Boston chat at a Skip the Small Talk event at Trident Booksellers & Cafe in April. Josh Reynolds for The Boston Globe

Nicole Raheja, who is in her thirties, has liked meeting newcomers to the area.

“They’re actively looking to try to make new friends,” she said. “You don’t feel like you’re trying to break in with somebody who already has had the same friends since they were a kid.”

Even though romance is not the theme of the regular Skip the Small Talk Nights, the experience can be helpful for dating.


Jacob Baker, 24, who drove from Hudson to one of the events held at Trident, said people understand that unless a Small Talk event is labeled as a date night (there are some devoted to that), it’s just about platonic conversation. He went to improve his conversation skills — something that would help him with dates later.

“It kind of feels like everyone’s starting at square one again. So I took this opportunity to take a step along with everyone else and push myself beyond my usual boundaries into this social world.”

Baker said Kirsner does a good job of making sure guests understand no one has to share contact information with anyone they talk to. People are allowed to offer their own, but it’s common for two strangers to have a deep conversation and walk away without any obligations.

Kirsner said the tables turned recently when a clinical psychology researcher asked to study Skip the Small Talk and its effects. Kirsner learned plenty about what the nights do for people.

“My favorite little tidbit was that the worse mood you were in when you came into the event, the greater the mood boost you felt after leaving,” Kirsner said. “If you’re like super skeptical about this event and think it’s gonna suck, you are actually the perfect person to come.”

For the schedule of events, visit www.skipthesmalltalk.com.

Meredith Goldstein writes the Love Letters advice column. Send your relationship and dating questions to loveletters@globe.com. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts.


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