How Do I Keep The Conversation Going Without Trying Too Hard

If you feel like you are carrying the entire conversation, this guide shows you how to keep things flowing naturally without chasing or forcing effort.

By
Josh Felgoise

Dec 8, 2025

Jacob Elordi

Conversation should feel easy, mutual, and steady. But a lot of guys feel like they are the only ones trying. You send questions. You keep it moving. You do all the work. And suddenly it feels like you are performing instead of connecting.

So let me answer this right away.

You keep a conversation going by matching effort, not manufacturing momentum. If you are the only one pushing, you are not building a connection. You are building pressure. Real conversation comes from shared interest, not from you trying to fill every silence.

If your mind starts spiraling when it gets quiet, reading How To Stop Overthinking Everything can help before you keep going.


If they want to talk, they will talk

One of the clearest lines from Episode 129 sets the tone:

“I think if somebody wants to see you, they’ll make it happen.”

Apply that to communication.

If they want to talk to you, they will talk to you.
If they want the conversation to continue, they will continue it.
If they want to get to know you, they will match you.

When someone is not matching, that is your signal to slow down, not speed up.


Do not carry the entire conversation

When the conversation feels one sided, you start feeling pressure to keep it alive.

But the exact line that tells you what to do is:

“If you feel like you’re having to put pressure on something… maybe this person isn’t the one.”

Conversation should not feel like weightlifting.
If you feel strain, tension, or responsibility to keep it going, the energy is not mutual.

Mutual interest feels effortless.


Stop trying to be entertaining

Most guys try too hard when they think the other person is losing interest.

You start:

  • asking too many questions

  • sending longer messages

  • over explaining

  • trying to be funny

  • trying to impress

But here is the truth:

Trying harder makes the conversation worse.
Matching their energy makes it better.


How to keep a conversation going the right way

1. Respond in your natural voice

You are not performing.

2. Ask one question at a time

Let them lean in too.

3. Keep messages short and easy to reply to

You want rhythm, not essays.

4. Mirror their tone and effort

Energy matching is everything.

5. Let silence happen

Silence is not danger. Silence is information.


When to stop trying

This line from Episode 129 is the anchor:

“I don’t think you should be chasing.”

If you feel like you are chasing during the conversation, it is time to pull back.
A conversation that only moves when you push it is not a conversation worth continuing.


Where You Go From Here

Keeping a conversation going is not about effort. It is about alignment. When someone wants to talk to you, the energy is obvious. When someone does not, the silence says everything.

If you want the next step, read How Do I Start A Conversation After Getting Her Number next.


FAQ

How do I keep the conversation going without overdoing it
Match their energy, not your anxiety.

What if they send dry replies
Pull back. Dry texting is information.

Should I send voice notes or long texts
Not if you are trying to compensate.

What if they stop replying
Let the silence answer the question.

Should I try harder
No. Effort should be mutual.


Episodes Referenced

For deeper insight, listen to Episode 129 of the Guyset Podcast.