What Men Won’t Say (Even When Asked)

I recently went to a Skip the Small Talk event. It’s exactly what it sounds like. A gathering designed to help strangers skip the usual surface-level stuff and connect faster through questions rooted in psychology.

I wasn’t going to make friends or seek connection. I went more as an observer. Part of my Heart-Strong Adventure is to experience things firsthand instead of just reading about them. I wanted to see how quickly people could connect if the questions were right. How vulnerable people were willing to get. How fast they’d open up.

I expected a younger crowd. I was right. Most people were probably 25 to 35. I was definitely the oldest at 48.

I also expected it would be mostly women. I was wrong.

There were eight of us. Five men. Three women.

That ratio surprised me. And the more the night went on, the more it told me something about what men are seeking, whether they know it or not.

Men Showed Up

I don’t think any of the men there were looking for romance. I think they were looking for friendship. For connection. One of the guys was married, as am I. Another mentioned his parents wanting him to find a partner, but when I asked if that’s what he wanted, the real answer was simpler. He was tired of going places alone.

One guy drove over an hour to get there. He said there wasn’t much like this where he lived. Another talked about how his trivia group fell apart after a friend moved away to care for his sick mom, who later passed.

You could see it. The loneliness. The hunger for something real. Men willing to put themselves in a situation that was probably uncomfortable because they needed it.

And yet…

The Contrast Was Stark

The women in the room opened up instantly. Naturally. The questions were designed to go deeper, to get people past the usual posturing, and the women went there without hesitation. The conversation flowed. It felt easy.

With the men, it was different.

Even with questions specifically designed to encourage vulnerability, most of the guys stayed surface level. They’d answer, but carefully. Politely. They’d talk about what they did, what they’d accomplished, where they were from. Safe territory.

I’d probe. Ask follow-up questions. Sometimes I could get them to go a little deeper. But even then, you could see the labor. The effort it took to get there. Some of them couldn’t go there at all, no matter how much space I tried to create.

One conversation sticks with me. A younger guy was talking about what he’s thinking about most these days. He said it was about what’s next. He had a job he loved. A house. Now he was thinking about relationships and family.

He mentioned he doesn’t like going to things alone. Family events. Traveling. He went to London by himself recently and it was cool. But, it would have been much better to have shared the experience with someone.

His parents really want him to have a partner. I asked if that’s what he wanted.

He said yeah. He’s getting tired of going places alone.

So, I asked another question. Is what you’re seeking a romantic partner? Or is it just human connection? Whether that’s with a partner or just other guys to share life with?

He paused. Then said, “Yeah. It’s more about the connection.”

I had to claw that out of him. And he was one of the more open ones.

What Came Up for Me

At one point, Heart-Strong came up naturally in conversation. With the women, they lit up. They wanted to know more. They asked questions. We exchanged information so they could follow along.

I mentioned it to one of the guys. And I watched his face change. There was skepticism. Almost like what I was saying felt like an insult. Like I was suggesting something was wrong with him.

I explained more. That I’m not saying men are bad. I’m saying culture has created expectations of men that are really hard to fill. And it’s causing a lot of suffering. It’s causing men to live from a place of fear instead of love.

As I kept talking, I could see him soften. Open up a little. But it was work.

What This Reveals to Me

Men are seeking connection desperately. Five men showed up to this event. One drove over an hour. They put themselves in an uncomfortable situation because they needed it.

But even with questions designed to help them go deeper, most of them couldn’t get there. Or wouldn’t. Or didn’t know how.

The women didn’t have that struggle. They went there instantly. Naturally.

That contrast is the thing I can’t stop thinking about.

This wasn’t about the questions failing. The questions were good. The structure was solid. Skip the Small Talk has clearly thought this through. They’ve rooted their approach in research about reducing loneliness and encouraging self-disclosure.

But even with all that scaffolding, the men still labored to access vulnerability. To move past the posturing. To express what was actually inside them.

The loneliness epidemic isn’t just about men being alone. It’s about men being unable to reach for what they need, even when it’s offered. Even when they’re in a room full of people asking them to share. Even when they drove an hour to get there.

What I’m Sitting With

I left that event feeling a mix of things.

Concern, because the pattern runs so deep. Hope, because spaces like this exist and men are showing up. Curiosity, because I’m starting to understand how much work it takes to undo what culture has done to men’s ability to connect. And gratitude. Because this is exactly the kind of firsthand experience that helps me understand what I’m exploring this year.

Men need connection. They’re seeking it. They’re showing up for it. But somewhere along the way, we’ve made it really hard for them to access it. I think that’s worth paying attention to.