August 01, 2016


Conversation - How to never run out of things to say and make every conversation interesting

This article is lesson 2 of 6 in our Six Frustrations series.

You see a woman across the bar who flashes you some eyes. Somehow you find the courage to walk over and introduce yourself. She smiles flirtatiously and gives you her name. Your mind is racing trying to think of something to say...


Uh oh, you never planned this far ahead.


You stammer a bit and manage to get out “So...uh what are you doing tonight?” and immediately regret how dumb it sounds.


Her smile starts to fade as she realises you may not be as confident and charming as she thought. After she tells you how she’s seeing some old friends tonight you manage to follow up with “Yeah that’s awesome, I love seeing old friends too...” an awkward silence and a forced smile appears on her lips before she politely excuses herself to go back to her group and you’re left standing there wondering how you managed to mess it up so badly.


This scenario probably sounds all too familiar for you, and when we sent out our survey the other week asking you what your main frustrations with dating are, this was your number two answer compromising twenty one percent of the responses. Welcome to the second biggest problem guys face with women: keeping a conversation going.


Before we dive into this topic we need to get a couple things out of the way with regards to how men see social situations. Many guys feel the solution to keeping a conversation going with a woman involves planning a long list of things to say that he can jump into incase he draws a blank.


While I’m not against planning in almost all aspects of self improvement, when it comes to social situations and conversation, it’s a terrible idea. Planning your conversation forces you into logical frame and it's the completely wrong headspace for socializing. In this case, it’s important to deal with the root cause of this need to plan, which is the FEAR of not knowing what to say next.  How do we deal with that?


The trick to dealing with the fear is to accept it. It’s going to happen, you’re going to run into situations in which you won’t know what to say next, and it’s going to happen often. Forever.


Every night I go out I run into this situation and I know it will never go away. This is true for anyone, even guys who are amazing with women. We all have these moments. The solution to these situations is not "I’ll memorize dozens of routines!" the solution is "I will stop caring that I have nothing planned to say." Accept it, relax, smile, look her in the eyes and realize that life is full of these moments and it's nothing to be stressed about. You'll find that conversation comes naturally when you can do this.


Here’s something to think about:

Whether or not a woman feels you are awkward has nothing to do with what you say, or even if you have nothing to say, it’s entirely dependant on how YOU feel in that moment. Running out of things to say doesn’t make women feel uncomfortable, running out of things to say and then FEELING awkward about it makes women uncomfortable.


This is the secret to natural conversation, it’s not about appearing or acting comfortable, It’s about feeling comfortable. If you can do this, you will NEVER run out of things to say. The irony is that the only way to consistently achieve this is to be content with it not happening. The fear of it possibly happening is what causes it to happen!


“The consciousness of self is the greatest hindrance to the proper execution of all physical action.”

 -Bruce Lee

Ok, now that we’re comfortable with the inevitability of not knowing what to say. What should we be saying now that we’re comfortable, or:


“What does an interesting conversation sound like?”


One way to always make sure your conversations are interesting is to talk about something you’re passionate about. It doesn’t even have to be anything that interesting. Think about the conversations you have with your friends, do you ever feel the need to keep talking just to be saying something? No! You talk about things that pop into your head, or that you care about. This is called having a connection and it's easy to do with friends because the connection has already been established. But how do you do this with strangers?


Often when we meet people for the first time we over analyse everything we're thinking about saying before we say it, and as a result what comes out sounds forced and lacks authenticity. This is fine when meeting people in formal or work situations, as the content of what you're saying carries more weight. In social situations however, this communicates that you're nervous, and she's going to wonder why.


When we speak about things we're passionate about we tend to bypass this logical self-filtering mechanism and speak from true emotions, this makes the conversation automatically become interesting.


If you want to make every conversation you find yourself in from now on interesting, here's a secret:


You need to become passionate about meeting new people.


If you can genuinely do that, people will find you charming. There’s a couple questions I always have when meeting women for the first time that communicate this:

1. How are they portraying themselves?

2. Who are they really?


Trying to find the answer to these questions is how I usually converse with women upon first meeting. So let’s break it down into a few examples.


How are they portraying themselves?


How is she dressed? How did she present herself when you met or saw her? Is she talkative or more quiet and reserved? This is all relevant information to answer this question. Try making the following statement:

“So what do you do? Wait, let me guess…”


Now make a guess that is based on the above information. Dressed sharp and was talkative and confident? Maybe she’s in sales or marketing. Dressed a bit more reserved, and is quiet or soft spoken? Maybe she’s in health care. Dressed provocatively and has a bit more flair to her personality? Maybe she’s an artist.


The point of this isn’t to guess correctly, it is to let her know that you’re making a statement based around how she presented herself. This is often one of the most interesting subjects for women upon first meeting because it directly relates to how she is perceived by others, which is something they most likely put a LOT of thought into. It also says something about you and will open her up to wanting to know what it is you do.  


Who are they really?


This one is a bit more deep, and requires some interest from her before answering. People won’t necessarily give this information out to strangers, so answering this question may take some time as she needs to be comfortable enough with you to share it. Who was she in high school? What are her life goals? What is she passionate about? These are all questions that would answer this question and help create a genuine connection in the process if your personalities align.


In the end conversation is about finding out about each other in a fun and comfortable way that creates opportunities to build attraction through a solid connection. There’s a lot more to conversation than what I described here, and it is a subject we spend a  substantial amount of time with in all our seminar and live training courses. Like anything else, practice makes perfect, but understanding the fundamentals of how a conversation works will allow you to have confidence in knowing that you’re coming across in the most positive way possible, no matter what the situation is.


Remember: talk about your passions, foster a passion for meeting new people, and then find out about them. Treat every interaction as if you may be meeting your future wife. You might be.

~Derek Cajun


For more on the six most common frustrations that men face in dating, check out our article on the Six Frustrations of the Single Man. 

Chris Shepherd and I recently released a 40 minute audio guide on being a better conversationalist. Here's a recording of the first 10 minutes. 

Click here for the product page
Cajun LS
Cajun LS


3 Responses


September 12, 2016

I am passionate about; Politics, Religion, Money, Healthcare, Traditionally taboo subjects Should these brought up into conversation early or later or never? Tone is a major consideration, don’t be a blow-hard.


September 07, 2016

I guess I call you Cajun. Cajun that has got to be one of the best articles on conversation I’ve ever read and I’m quite impressed with its logic and simplicity of conversation and our ability. Either way bravo. I wish I could talk to you about this complex, to me anyway, problem I’m having with girl tha5s so dear and sweet 5o my heart. At least some advice cause I bailed on it and I feel all so rotten, but I got sick of being blue all the time. I love her in so many ways and for so many reasons it just hurts me all around. Well great article Cajun rock on. :-(-:

Renaldo Alin Pop
Renaldo Alin Pop

August 03, 2016

Would you write a small guide on tinder texting ? I’m curious about your take on this new dating trend that the whole world is using now.

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