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Never Run Out Of Things To Say Again (How To Keep A Conversation Going With A Girl)

November 29, 2018

You walk up to a beautiful girl and say,  “Hey, I like your style.”

She smiles and says, “Thanks!”

She’s waiting for you to sweep her off her feet with your charming personality. But you can’t think of anything to say. So, you just walk away, embarrassed that you missed your opportunity to get a date.

Sometimes the hardest part of attracting women is thinking of the right thing to say. But it doesn’t have to be.

In this article, you will learn how to keep your conversations with women flowing – even if you’re feeling nervous. You’ll also discover how you can turn surface level logical conversations into emotionally impactful conversations that a woman will never forget.

How To Keep A Conversation Going With A Girl Part 1: Breaking The Ice

Once you’ve approached a girl, you have to build an interesting conversation out of thin air.

Overall, this is a skill that you’ll develop with practice. The more you put yourself on the spot by approaching women, the better you’ll get at thinking on your feet.

In the short term, you can make starting a conversation with a girl easier by memorizing a few basic questions.

Whenever you can’t think of something to say in the moment, you can fall back to one of the questions you’ve memorized.

Here’s a few examples:

  • “What do you do for fun?”
  • “What are you passionate about?”
  • “Are you from here?”
  • “What do you do for work?
  • “What are you doing later?” (this helps you get a sense of how much time she has to hang out with you)

These questions aren’t magical, but they can get a conversation started: think of them as a crutch to fall back on when you can’t think of something interesting to say in the moment.

When asking these basic questions you’re looking for commonalities that you can expand on:

  • For example, if you ask a girl what she does for fun, she might say she likes to watch Netflix. You could follow up by asking what she’s been watching lately. If she says she’s been watching Game Of Throne,s you might respond by asking, “Who do you think is going to survive in the final season?
  • If a girl says she’s passionate about helping people, you can talk about how Tim Ferris’ book, The 4 Hour Workweek inspired you to start your own online business and it completely changed you life. You could go on to explain how that experience made you realize that helping others is one of the most important things you can do – you really can improve someone’s life for the better.

If you can’t think of anything to say about a particular topic, just move on to something else by asking another question.

Now, we all instinctively know how to hold a good conversation, but when we’re under a lot of social pressure, we start overthinking instead of letting the conversation flow naturally.

That’s why it’s useful to memorize a few basic questions you can ask any girl you meet. Doing this will give you something to say so that you can keep the conversation going until you can break the ice.

How To Keep A Conversation Going With A Girl Part 2:The Power Of Free Association

Whenever a girl says something, you can associate off what she said to deepen the conversation. If you get good at doing this, you will never run out of things to say again.

If you think about it, anyone you’ve met who was particularly interesting or funny was good at free associating. They stood out because of their ability to relate what you said to something unexpected and creative.

At this point, I can pretty much make a girl burst out in laughter whenever I want to simply because I’ve practiced free associating so much.

Let’s take an example. When a girl tells me her name is Ashley, my mind automatically creates a list of associations. It looks something like this:

Ashley = Attractive / Wealthy / Generic / White / Ashley Benson.

I can then say something based off any of those associations, for example:


“Ashley? That’s a classic hot girl name. I’m not sure if it fits you.”


Me: “I’ve never met an Ashley before.”

Her: “Really?”

Me: “No, I’m messing with you, I’ve met tons of Ashley’s.”

Ashley Benson:

“Ashley? Like the actress Ashley Benson. So you’re a Pretty Little Liar?”

Wealthy :

“Most of the Ashley’s I’ve met were really rich. But you look like you’re the exception.”


“That’s the ultimate white girl name. You must be from Scottsdale.” (Scottsdale is the rich white part of my city.)

Even from just hearing a girl’s name, you can use free association start building an engaging, emotionally charged conversation.

Of course, just knowing why this concept is so powerful isn’t really going to allow you to make a change in your life. Fortunately, your ability to free associate is a mental muscle that you can develop with practice.

I do two exercises every single day that have allowed me to effortlessly generate interesting things to say when I’m interacting with women. If you spend two minutes a day practicing each of these, your conversation skills will skyrocket.

Exercise 1: Free-Associate Sentences

For this exercise, complete a sentence out-loud, then create a new sentence using a word from the previous sentence (You can also do this silently in your head ).


  1. The universe has existed for billions of years.
  2. I am 25 years old today, that’s halfway to 50.
  3. Half of marriages end in divorce.
  4. Marriage is known to be a cultural universal which is strange because I read that monogamy isn’t natural.
  5. Reading good books is one of the best ways to improve your life.
  6. If you’re not improving, you’re slowly getting worse.

Practicing this exercise will help you to make creative connections naturally in all of your conversations.

Exercise 2: Chain of Associations

In this exercise, you’re associating singular words instead of sentences. But there’s a twist, you are specifically thinking of words that have an emotional charge.

Doing this exercise might look something like this:

Love – Sex – Virgin – Mormon – Cult – Manipulation – Salesmen – Annoying – Amy Schumer – Gross – Taco Bell – Obesity – America – Freedom.

Men often struggle with women because their conversations are too agreeable and logical. These men might have a nice conversation with a girl, but they don’t challenge or excite her. A safe conversation will never offend a girl, but it will also never turn her on.

Guidelines For The Chain of Associations

Your goal when doing this exercise is to associate words that provoke a strong emotional reaction. (That emotion can be either negative or positive.)

While you’re doing the exercise, don’t overthink it. Not every word you associate has to be controversial or shocking; it’s okay if some of the words you think of are relatively bland.

This exercise will teach your mind to make connections that are outside the boring, logical, safe topics that most guys rely on when talking to women. As you practice this, your conversations with women will become increasingly impactful.

TheRedArchive is an archive of Red Pill content, including various subreddits and blogs. This post has been archived from the blog Red Pill Theory.

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Post Information
Title Never Run Out Of Things To Say Again (How To Keep A Conversation Going With A Girl)
Author Avery
Date November 29, 2018 8:30 AM UTC (3 years ago)
Blog Red Pill Theory
Archive Link https://theredarchive.com/blog/Red-Pill-Theory/never-run-out-of-things-to-say-again-how-to-keep-a.22630
Original Link https://redpilltheory.com/2018/11/29/never-run-out-of-things-to-say-again-how-to-keep-a-conversation-going-with-a-girl/
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