15 Methods and Mindset Tricks to Make you a More Interesting Conversationalist

By Jonathan Roseland

Being a great conversationalist requires a combination of mindset and methods.

Luckily though you can fake it till you make it. Here I will cover how to steal a conversation while appearing magnanimous, a sweet body language trick, applying economics concepts to increase the attention people show you, and my favorite "pick up line" to starting a conversation.

Start conversations with a question

Start conversations

You want to begin your conversation with a bang (first impressions matter!) so if possible start with an open-ended question that is relevant to the environment that will engage your new friends.

The best "pick up line" to begin an interesting conversation

couple date romance

Line: Pardon me. Do you mind if I get your opinion on something...?

Follow this up with an engaging question, here are a few I like...

  • Can you recommend any unique cocktails here?
  • Do you know this town well? Can you recommend a restaurant/bar, etc?
  • Where did you buy that clothing item/accessory/cell phone?
  • What do you think of this event?

Do check out my funny video about How to Pick Up Chicks in the Club

Applying relational economics to conversation


This is a very important concept to grasp so please pay attention. Imagine that your relationship is like a bank, you can make emotional withdrawals and emotional deposits to this bank. If the balance gets too low then the relationship is over or becomes very unpleasant. This applies to any relationship be it your mom or the person you just met at the bar. Here are some examples in a conversational context...

Emotional Deposit

Emotional Withdrawals

  • Affirming or agreeing with them
  • Positive body language
  • Use their name
  • Demonstrate you are listening & understanding what they are saying 
  • Giving an answer
  • Asking a question about them or centric to what they are discussing
  • A strategic well thought out compliment
  • Asking for their opinion
  • Telling a joke
  • Encouraging their ideas
  • Disagreeing with them
  • Negative body language
  • Talking about yourself
  • Asking a question about an unrelated topic
  • Asking them a personal question when it’s not relevant to the situation
  • Flattery or a disingenuous compliment
  • Advertising or selling to them
  • Lying

A brand new conversation is starting basically at very close to a zero balance, if you make too many withdrawals you’re done!

Conversational-relational supply and demand arbitrage

supply and demand
Continuing the metaphor of our relationships being a bank we want to practice a little supply and demand arbitrage to make people more interested in us. Here's how this is done; make a large emotional deposit. Then make a withdrawal, if possible use humor. What you are doing is giving them an emotional high, associated with you, and then taking it away. True to human form we want what's been taken away from us even more. Here's an example of how this could be done.

Jonathan: Chris I'm really impressed with how you've been able to take something that you are passionate about and make a living helping people. What was it that inspired you to first try this?
Chris: Thanks, Jonathan! What inspired me was...
Jonathan: You are going about your marketing all wrong. You aren't going to meet your goals if you keep doing things that way. I have a marketing firm and I've produced some really spectacular results for clients in similar businesses to yours. I think I have some ideas that could help.

Don't go too overboard with this method though! Too much of an emotional rollercoaster will not make for good relationships

Body language mirroring

This is the practice of copying the gestures and posture of the person you are chatting with. Are their legs crossed? Cross yours. Are their hands on the table? Put your hands on the table. Fairly simple. Timing is the key to maximizing the effectiveness of this technique. Wait till they mention...

  • Something that you find interesting
  • Something that they think you will find interesting
  • Something they are proud of

Then mirror them. This subconsciously communicates that you empathize with the way they feel about whatever topic. A little while later break the mirroring, on a subconscious level they will wonder if they said something wrong and it will increase their interest level in you. Then mirror them again at a high point in the conversation.

How to talk about yourself and NOT be boring

You may be an absolutely fascinating person but the majority of people just don't want to hear you talking about yourself. As you can imagine as a continuation of the economics metaphor, if you make a large emotional deposit first they will pay a whole lot more attention and be more interested in what you have to say about yourself. Alternate between making emotional deposits but keep talking about how interesting you are and what you do.

Practice topic depth escalation

Go Deep
It's well said that small minds talk about people, moderate minds talk about events and great minds talk about ideas. You can rarely begin a conversation by diving into deep conceptual territory. So you want to start with small talk and humorous banter, then ask people's opinions on an event that occurred recently, then transition into talking about ideas surrounding the event. Example:

Conversation Intro: Hey how has your day been?
Event: Are you and Tracy doing anything special for valentine's day?
Idea: I saw this blog on the internet recently about how our modern-day concept of love is completely skewed from the traditional definition of love which is that of ongoing acts of sacrifice to something great than oneself.
If you want to do a controversial issue idea, you can always ask "How would you respond to people who say...?" This way, you haven't directly challenged someone but you have introduced another element into the conversation.

Ask them to be interesting

Be interesting

Pretty much everyone is interesting in their own way and they probably don't get to share it nearly as much as they would like to. So give them the opportunity and they will think the world of you. Here's the simple line I like to use:

So tell me something interesting about yourself, Chris?

This is a great line that makes you seem charismatic as well as lets you know what they find interesting, which will surely make for good conversation.

How to ask people what they do

What do you do
You will come across as more interesting if you ask the question this way.

So how do you spend your time when you aren't __________________?

The blank should be something relevant to the context, environment, or something that you know about them. Examples:

So how do you spend your time when you aren't writing fascinating blog posts?
So how do you spend your time when you aren't on Facebook?
So how do you spend your time when you aren't hanging out with beautiful women?
So how do you spend your time when you aren't at the gym?

Demonstrate your listening skills

listening skills

If you are going to focus on one thing to make you a better conversationalist I would say to improve your listening skills. This will be another blog subject altogether. When they are talking about a subject they find interesting follow up with this question:

"That's interesting ... say more about that..."

Also ask probing questions such as:

So what influenced you to make that decision?

Speaking pace

speaking pace

In general, fast-paced speech is a sign of nervousness and slow-paced speech is a sign of confidence. So most of the time I go with a slower pace but if I'm talking with someone who has a noticeably fast pace then I will mirror them and go fast.

Magnanimous conversation stealing

This has probably happened to you before; you are discussing something, someone else jumps in and makes the conversation all about them. This is called conversation stealing and it's annoying if you do it wrong.



The correct way to do it is to make an emotional deposit before the steal and then make an emotional deposit at the end of the steal. That way you are keeping the attention high throughout and you don't look like a jerk for stealing the conversation. Example:

Chris: So my kid is just doing awesome at football practice.
Me: That's great. I definitely know where he gets his work ethic from! My kid just got his black belt in Karate and is traveling to Korea for a student exchange program. Since you've traveled abroad extensively in Asia can you give me some suggestions to give to him?

As you can see here I made an emotional deposit first by complimenting Chris and his kid, I stole the conversation and then I linked it right back to him and made another emotional deposit.

Compliment strategically


Compliments are a very powerful tool when used correctly, the right way to them is to compliment people on the things they are proud of. For example:

  • if a person is in great shape and obviously spends a lot of time in the gym, compliment them on their work ethic and commitment to taking care of themselves.
  • If someone is particularly successful in their career or business compliment them on their intelligence, creativity, and insights to capitalize on opportunity.
  • If someone is particularly well dressed compliment them on their good taste.

What you don't want to do is compliment people on things that they were born with or did not have to work for. For example: Don't tell a gorgeous young girl that she is beautiful, she already knows this well and probably hasn't worked at all for it.

However, there are situations where people are proud or have a sense of entitlement that you can compliment if you want to stroke their ego. For example, I have a very distinctive last name, when people tell me that they like it they just made an emotional deposit with me of about $100,000!

Silly sexy word game

Here's an awesome situational banter game for flirting in a social environment. So you are talking to a group of girls (or guys) and you say: Hey you want to play an interesting game?

They will say yes. Then you say...

Ok here's the game. I am going to say some words. When I say these words you have to tell me the very first thing that comes into your mind within the first 2 seconds. You can't tell me what you think I want to hear you. You have to tell the truth.

Now you begin saying some phrases...

Money, Power, Married, American, Missionary, Job, Scared, Hard Work, Doggy, Protection, Tower

As you can see the phrases are getting sexual, so the girls should start thinking about sex and start telling you the sexy things they associate with the phrases. Now you can banter about them having dirty minds. If they don't start thinking dirty you can joke about them needing to eat more oysters to strengthen their libido. This game is pretty sexual so I would only use it if your target group seems like they are going to be receptive.

Merge groups

merge groups
If you are at a party or social event there will be multiple groups of people standing around chatting. Over the course of the event, you will migrate between different groups. As you see one of your previous groups in physical proximity to your current group invite them to join together. Make a joke about this if appropriate:

I have some more friends over here to introduce you all to, can I arrange a merger and acquisition of our groups?

You are going to be excellent at remembering names since you are going to check out the AV Association technique; you will remember the names of everyone in each group and can introduce everyone. This makes you look like a true social Rockstar and sets you up as the dominant leader of both groups. Actually being able to pull this off will increase your social proof by about 10,000%!

Want to take your networking game to the next level? Give a listen to this audio chapter from my book...

How to Be Cross Eyed [Second Edition]
Category: Book


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