How Easy Are You to Talk To?

Estimated reading time: 4 minutes


It’s easy to focus on other people:

  • Are they interesting?

  • Are they funny?

  • Do they know how to flirt?

I’d like to challenge you with a different question: how easy are you to talk to?

The Basics

Colorful mosaic artwork showing abstract faces and expressive shapes, suggesting communication and interaction

Small things — eye contact, curiosity, listening — shape the entire interaction.

This may seem obvious, but it’s worth going through the basics — because they’re often overlooked.

  • making eye contact

  • smiling

  • showing curiosity (especially through open-ended or follow-up questions)

  • active listening (not multitasking, reflecting back what you’ve heard)

  • gradually sharing about yourself in layers (how much you share, and how personal it gets)

Individually, these don’t seem like much.

But together, they shape whether a conversation feels easy or like work.

When Conversations Don’t Work

Sometimes it feels like you’re talking — just not to each other.

Some common complaints I hear from both men and women:

  • “I feel like I’m doing all the talking.”

  • “They didn’t ask me anything.”

  • “They talked a lot.”

  • “I felt like I was being interviewed.”

Most conversations that don’t work tend to miss the middle. Or what I like to think of as breaking the Goldilocks principle: too little or too much.

On one end, it’s too much.

You ask a lot of questions — sometimes multiple in a row. You tell long stories without leaving much room for the other person. You might even feel like you’re carrying the conversation.

On the other end, it’s too little.

You give short answers. You ask few (if any) questions. And when you do, they stick to facts or lead to yes/no responses. The interaction can start to feel a bit transactional.

Somewhere in between is where conversations start to feel natural — not perfectly balanced, just responsive.

Do you tend to fall on either end of the spectrum?

Conversations are a Tennis Rally

Overhead view of two people rallying on a tennis court, positioned on opposite sides of the net

A good conversation doesn’t need to be impressive — just a steady back-and-forth.

You may be friendly. You may be nice. You may even ask lots of questions. You might be more of a talker or more of a listener.

And still be hard to talk to.

It’s less about how much effort or time you put into a conversation, and more about how collaborative it actually feels.

Think of it like a casual tennis rally: You hit the ball over. The other person hits it back. There’s a rhythm. Nothing fancy — just keeping it going.

If one person keeps hitting balls without paying attention to the return, it starts to feel off.

And if one person barely returns anything at all, the rally never really gets going.

Conversation works the same way.

It’s not just about showing interest. It’s also about giving the other person something to engage with.

Are you sharing anything about yourself?
Are you reacting to what they say?
Are you making it easy for them to respond?

If not, the interaction can start to feel one-sided — even if you’re trying.

What to Make of Poor Conversations

A conversation that doesn’t flow can mean different things. Sometimes it’s nerves; sometimes it’s a bad day. And sometimes… it’s simply not a good fit.

It’s not always obvious which one you’re dealing with. So, as I often say: it depends.

Part of dating is deciding:

Do I want to give this another shot?

And it’s okay if the answer is “no”.

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How Much of Dating Is Luck?