An awkward silence is one of our greatest fears - especially when we're on a first date with Mr. hot and charming. We know we want to say something before he gives up hope and leaves talking to himself...but we just can't think of anything interesting to say! Read on for ideas!

Obviously, asking “and how are you now?” for the fifth time in a single evening is not cool. It’s definitely not how to keep a conversation going…at least not a good conversation.

Picture the scene:
You’re on a first date. You’ve brought your ice-breaking game to the table, and you’ve breezed through the first thirty minutes. You listened, you were funny and you asked great questions. It was a dream and you clearly know how to keep a conversation going with a guy!

But you’ve now asked a redundant, closed ended question that required only a one word answer: “No.

In just one swooping monosyllable, you’ve both conspired to kill the conversation dead in it’s tracks. You don’t know what to say next, and by the looks of his awkward shuffling and darting eyes, neither does he.

Uh-oh- This is real. The pressure is on. And in minutes he’s probably going to receive the standard “emergency phone call from his buddy Harry who’s got stuck in the bath”.

The Fear Is Real

The fear of awkward silences is so universal that it almost always seems to pop up in movies and sitcoms. In Pulp Fiction, Uma Thurman’s character reasons that when two people start to actually feel comfortable during lulls in conversation, it means they dig each other.

In the oldie but goodie hit U.S. sitcom Everybody Loves Raymond, Ray and his wife Deborah analyze silences between partners from a longer-term perspective. Instead of feeling awkward whenever there is a huge pause between someone talking, they instead begin to worry that after so many years of marriage, they’ve actually ran out of things to say to one another. Which is equally uncool.

As they discover, though, periods of pause just mean you’re so darn comfortable with one another that you don’t need to keep talking. You can just enjoy being with each other.

Unfortunately this is not always true in the early stages of a relationship where silences can be super awkward.

How To Keep A Conversation Going With A Guy

If you’ve had a few conversational lulls in the past and just the very thought of them gives you the chills, follow these top tips and turn yourself into a pro communicator and be a master of banter lines for texting in no time flat.

1. Resurrect The Last Topic

So you seemingly asked a closed ended question, he gave you a blunt monosyllabic reply, and boom, that seems to have exhausted that topic.

So what do you do?

You could resurrect the last topic you just discussed, and which he seemingly made redundant. For example, if you asked whether or not he still sees his parents and he answered “NO”, you could get him to expand by saying: “Would you like to see them again?”.

Fun scale: pretty low.

A better approach is to refer back to a previous conversation or topic and add a funny twist.

For example:

“Hey! Remember when we were talking about our favorite comfort foods? Well, I just had this random thought: If you could create a bizarre food combination that surprisingly tastes amazing, what would it be? I think mine would be spaghetti tacos!”

To seal the deal, suggest a date night bringing to life your creations.

2. Bring Up A Related Subject

If a conversation feels flat and you don’t know how to keep a conversation going with a guy, you could bring up a related subject.

This is a technique that many of us rely on all the time during the everyday to’s and fro’s of a conversation. But because we do it unconsciously, we forget to rely on it whenever we feel put on the spot.

For example, if he was talking about his last Kite Surfing vacation in France, you could pick up this thread and talk about foreign languages. Maybe you could say how you’d like to become a digital nomad and live in Colombia for 6 months to learn Spanish.

From there you can carry the conversation to many areas – would he like to visit Colombia? What countries are on his bucket list? What is his favorites language, etc.

3. Become An Active Listener

When I was younger, I was really shy. I’d freeze up.

Then I started dating. To get me through the dates, I’d prepare a list of topics beforehand to talk about. But it still didn’t help because I was thinking about my list while the other person was talking (no bonus points there). It wasn’t until I worked on becoming a better listener that conversation really started to flow. So, stop. Listen. Take your time. Repeat. Learning how to keep a conversation going all starts with listening.

To be a good active listener, paraphrase when he is saying, and don’t be afraid to ask questions. And one last thing – avoid immediately jumping into your own thoughts or experiences until it’s the right time in the conversation.

4. Ask About His Passions

Guys (like us girls) love to talk about their passions, ideas and dreams. So, ask him an open-ended question about one of the three, and you could potentially keep him talking for quite some time. And the best part? You find out what really makes him tick and get to know him on a deeper level.

Here’s a suggestion on how to ask about his passions:

“Hey, I’m curious to know more about you and what you’re passionate about. Tell me, what are some of your favorite things to do?”

By using this approach, you convey genuine interest in his passions and give him the freedom to share with you what truly excites him. It opens the door for him to talk about various aspects of his life that make him happy (always a good thing). Remember to actively listen and engage in the conversation, showing enthusiasm and asking follow-up questions to delve deeper into what he finds important.

5. Keep It Positive

Good communicators know how to keep a conversation going by keeping it positive.

For example, if a guy is feeling down, and doesn’t seem to want to talk about why he’s feeling down, don’t keep asking him what’s wrong. Instead, ask him to name one thing right now that would improve the situation. Ask him how and not why.

How To Keep A Conversation Going With A Guy Final Thoughts

Think outside the box and try different ways of approaching subjects. Ask open ended questions and avoid the mundane and negative. Knowing how to keep a conversation going with a guy is an art – but one which can easily be learned one conversation at a time.


Claudia Cox

Claudia Cox is a modern communication expert who gives singles and couples alike the tools they need to improve their relationships. She is the creator of The Text Weapon Texting Club, and the author of French Seduction Made Easy. She loves the outdoors, baking tasty treats for friends, and of course, texting.
Learn more about French Seduction Made Easy.

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  1. I went out on a first date with this guy on tuesday, he was so interested and we even planned to go out again on saturday. I was waiting for him to text, but he didn’t text me and now two days have passed. Is it too late for me to text him? I have no problem of initiating the text, but I just dont want to force him into anything if he is not interested. If he hasn’t texted me after two days, doesn’t it mean that he is not interested?

    1. Hi Kiana,
      I’m sorry for the delay. I would suggest waiting for him to text you. If he hasn’t texted you in 2 days it doesn’t necessarily mean he isn’t interested. Maybe he read somewhere that he was supposed to wait, or maybe he was just really, really busy…regardless of the reason, I think it always works out better if the guy has to make the effort in the beginning (it follows the law of attraction).

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