Men On Apps Don’t Ask Questions (Because We All Need Help to Be Vulnerable)

why don’t men ask questions?

Ashley sat down with Meredith at Love Letters advice column and podcast to talk about a phenomenon that turned up in the Love Letters inbox: why don’t men on apps ask questions?

Listen to the full episode featuring the original advice seeker, Dr. Todd Kashdan, and Ashley here or wherever you get your podcasts. Search for the April 14, 2026 episode.

Below find a transcript of the excerpted conversation between Ashley and Meredith. This transcript has been lightly edited for flow and clarity.

Ashley Kirsner on How to Have Deeper Conversations

Host

Thinking about the regional part of it all, despite Massachusetts being a place where people don't always want to ask a bunch of personal questions, some people here are working to get better at it.

Ashley Kirsner runs Skip the Small Talk, a question asking event that started where I live but now runs in many cities, including Nashville, Philly, Denver, DC, and I see some chapters in Europe.

Ashley's background is that she's conducted research with professors at Cornell, the University of Miami, and at the Emotion Research Lab at Boston University.

Ashley started Skip the Small Talk about 10 years ago, inviting people to come to events as strangers. These were not necessarily dating events at all. Just get-to-know-you practice sessions.

She was trying to help people talk and connect.

The idea came from important work.

Ashley

I was volunteering at a suicide hotline and I was noticing that regardless of what people were calling in about, that people were very hesitant to share their inner struggles with the people they already knew.

So they were happy to spill their guts to a stranger, but when pressed, they would say that they didn't want to “be a burden on their loved ones”. They just “didn't talk about that sort of thing.”

And so I was almost wondering if I could get people to practice vulnerability in a more structured way. What would happen if we got people to, you know, talk to strangers about the meaningful stuff so that the stakes were low? It wouldn't feel like you were being a burden on anyone. You knew, everyone had opted in.

Host

If you go to a Skip the Small Talk event, you don't have to stress out about what to talk about.

Ashley has come up with questions and facilitators guide people through them.

Facilitator - Background Recording

Do have some cards?

They are at the tables and I'll also have a few questions up here.

On the screen you can choose the cards that you would like.

If you would like to take a card from a neighboring table, you can if you do not like your card.

Host

What I find fascinating is that people who show up for this, they want to ask questions.

In fact, they don't even want small talk. The program is literally called Skip the Small Talk.

That said, Ashley knows that if there wasn't a moderator to guide the question asking, people wouldn't know what to do, which might prove that even curious people who wish they could ask questions don't know how to get it going on their own.

Ashley

We kind of accidentally found out because every so often there's a venue where the microphone isn't working super well and the acoustics are bad and so people don't necessarily hear the instructions to use the question cards.

But it's so interesting because the way we found out was even though the question cards were on people's tables, they were not touching them!

And you could see the body language at the event was just not there.

I think we're all in this sort of societal moment where it's very difficult to convince yourself to be the first to be vulnerable.

The most interesting questions and the most connecting questions are the ones that are a little bit vulnerable to ask. And because we're all a little out of vulnerability practice, it's a lot harder to get yourself to ask the questions that are actually going to lead to real conversations.