How To Keep A First Date Conversation Going

Wondering how to keep the conversation going on a first date?

Well awesome, because that’s what we’re going to cover today!

Imagine you’re on a first date with an attractive woman, but before long, she starts to seem bored.

In fact, before you know it, you’re waist-deep into an awkward silence that no one was hoping for. (!)

Sound familiar?

If so, know that it’s normal to feel challenged about how to keep a first date conversation going.

Especially if you’re an introvert, you may feel on the spot or you simply may take more time to think things through before speaking, or both.

That said, this is an important skill because if you continue to be afraid of conversations dying down, what will happen then?

How will you connect with her enough for her to want to see you again on a second date?

Well, not to worry because that’s exactly what we’re about to address today…

  • First, we’re going to cover the two conversations you’re having on any date: words and proximity/touch.
  • Then we’ll go into each facet and how to succeed at both aspects.

So by the end of this post, you will be much more comfortable with how to keep a first date conversation going, which will also be of use to you in any conversation where there’s a spark of chemistry.


Why are conversation skills important in the first place?

When you can hold your own and find connections between yourself and the woman you’re on a date with, you both enjoy yourselves more.

And it helps you be more comfortable with conversations in general.

That said, you can only get so far with conversation skills if you don’t have a baseline of strong confidence in yourself as your own uniquely attractive man.

Otherwise, the self-doubt would cloud your mind and distract you from a quality conversation. So let’s avoid this with a powerful exercise, conveniently on page 8 of this free ebook.

This is our best free resource on building your confidence as an introverted man, and I’m excited for you to dive into it here!

Now, let’s get into our step-by-steps on how to keep a first date conversation going.


First, remember there are always two conversations going on.

This applies whenever you’re on a first date, second date, or even if you’ve just approached an attractive woman and have gotten into your first conversation.

You’re always in fact having two conversations: one is with words, and the other is with your proximity and touch.

Both are so important!

So the next time you’re on a first date with a woman, remember that it’s not just the content of what you’re saying; it’s the feeling in the air.

This will help you calm down in the moment if you don’t know all the perfect things to say because it’s not even about that. (!)

The most important thing is the overall connection created through these two conversation types.

Now, let’s discuss each point and how they fold together.


As for words…

When you know how to hold a first date conversation and keep it flowing, it takes the pressure off in the moment.

Instead of constantly trying to drum up something out of thin air, you can just relax and enjoy how things unfold.

You don’t have to come in with cue cards in your back pocket on various topics and steal a glance as she goes to the bathroom. That would be stressful!

And you don’t have to have the whole thing planned out. That would be stressful too.

Instead, you can simply follow the thread of conversation where it leads, which you can get really good at by listening well and noticing context clues.


Asking and sharing…

Asking and sharing are a couple of general ways you can steer the conversation:

  • Ask her a follow-up question on what she just shared (only things you’re interested in knowing the answer to!)
  • Share something from your own life experience that corresponds with something she just told you.

For example, let’s say she said that she just moved here.

In that case, you could…

  • Ask where she moved from, or
  • Share when you moved here.

Let the stories and conversation unfold from there, and then let’s say it turns somehow (as conversations tend to do!) to breakfast.

Now let’s say that she had the best breakfast this morning.

You could…

  • Ask her about what she had, or
  • Share what you love for breakfast.

Then talking about breakfast, you both love eggs, and that reminds you there’s a new place that opened up down the street that has the best omelettes.

Now let’s say she went also, and y’all talk about the service there, which reminds you of your first job as a waiter.

You can then…

  • Share more about that, or
  • Ask her what her first job was.

Do you see?

To keep a first date conversation going, you can simply follow the conversation where it leads.

That happens when you engage in the moment and either asking genuine follow-up questions or sharing genuine experiences.

But words aren’t the whole picture! There’s also proximity and touch, which is quite exciting.


As for proximity and touch…

No matter how skilled you are with words, what separates a conversation with a woman you find attractive from just any conversation is the chemistry in the air.

Reason being, whether you’ve just met or are on a date with her, it’s not platonic. So it shouldn’t be treated as such.

Now, don’t worry!

You don’t have to touch her constantly or even at all until y’all are already quite close together.

Instead, you can first notice how comfortable she seems to be with your current level of distance/closeness.

  • If she is backing away, then stay away.
  • And if she is neutral, inch a bit closer and see how she responds.

If she is neutral or warm, continue moving closer as is natural until either you see she’s not interested in which case you’d have given her much more space already (!) or until you’re feeling like she might be receptive to your touch.

Then you can touch her, your…

  • knee to hers,
  • shoulder to hers,
  • hand to her knee, or
  • arm to her hand.

See how simple and smooth it can be?


And if you do have an awkward silence…

That’s okay!

It’s only awkward if you make it that way.

Otherwise, it can actually work in y’all’s favor by increasing the exciting tension in the air.

Certainly, you don’t have to consider the conversation over. It’s not!

Rather, if you come across a silence, you can either…

(1) Bring in a new topic from what y’all had discussed before.

For example, from the scenario outlined above, you could bring up where she’s from, breakfast foods, that new restaurant, first jobs, or whatever else y’all talked about.


(2) Bring up something else you’re curious about or would like to share.

For example, a movie you watched on Netflix last night, your new archery class, or a trip that’s coming up on your calendar.


Conclusion on How To Keep a First Date Conversation Going

Now that you know how to keep a first date conversation going, you’ll be able to relax and enjoy the moment on your date so much more easily.

Let’s review what we went over today:

  • Remember there are two conversations: words and proximity/touch.
  • As for words, keep the conversation going through asking and sharing.
  • As for proximity and touch, lead while paying attention to how she’s responding to you.
  • And if there’s an awkward silence, simply bring up something from earlier or a new thing.

Now, what about conversation topics and tips in general for introverted men and first date venues that are great for introverts?

We’ve got articles on those here and here.


Where from here?

And now, if you want support on developing into the kind of man who any woman would enjoy first date conversations with and would be thrilled to go on a second date with, we can help!

Consider letting us support you in a personalized, customized way through our Launch Your Dating Life program.

While our free ebook is our best free resource, Launch Your Dating Life is how we partner with you, alongside you, to bring you the results you’re after in your love life while staying true to yourself.

If after reviewing this page, you’re considering joining, then apply to talk with us in a 1:1 phone call so we can see if the program is right for you!

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Sarah from IA
Sarah is founder and CEO of Introverted Alpha; the top dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of Introverted Alpha's 22-page ebook in the box below.

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Attracting An Amazing Girlfriend Starts With Finding Your Own Vibe.

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