Starting conversations with random individuals seems to be a sticking point of many people who want to gain anything from an interaction. They honestly end up screwing it up by moving the conversations in the wrong way. I know I’ve been a person who has made that mistake before; that’s a mistake I rarely make now. The key to starting a conversation with an individual is to know how to open up the conversation, which we will go into today.

Opening A Conversation

In my mind, the first step to getting to the conversation that you want to have is to be good at opening up a conversation. The good thing is, there are more than a couple of ways to open up a conversation. A few of them I use on a regular basis is the question, straightforward approach, and observations. In this post, I’ll break down each one and the key to them all, starting with the question.

Asking someone a question is one of the easiest ways to get them into a conversation; you can use this in more ways than you think. For example, as an individual, you may want to make new friends with classmates or just start getting to know people in general — this will help you. You can ask people just about any question you can think of because what a question does for you create a conversation topic for you both or the group. If you were to ask people about dogs, you can now start talking about dogs and bridge that into another conversation. That is one of the biggest keys; the question is just a bridge to anything you want to talk about with that person. I personally use a couple of common questions like: “How’s the weather?”, “What are you up to?”, “Can I get your opinion on something?”. All of these are easy ways to open up the conversation and allow you to bridge to something else; the opinion question is the easiest to take advantage of. Now, some other options that are open to you are the straightforward approach.

The straightforward approach implies just being blunt and saying hello to someone. There is not much finesse here and it could lead to a dead conversation very quickly. The important thing about this type of opener is to also use a compliment in most cases. If you can say something nice about a person, right after saying hello, you can make them feel a lot better about themselves and keep the conversation going by actively trying to talk about them and not yourself. But, the key here is to be really observant; you need to be able to have a genuine compliment for people when you are straightforward. This leads me easily into the last kind of opener, which is observations.

Observations are one of the easiest ways to get someone to invest in a conversation with you. By spotting and commenting on a specific feature or article of clothing, you can get them enthralled in a conversation. Once you’ve done that, you can take it a step further and start the conversation. This is one thing I practice myself when I talk to individuals. It makes it a lot easier to go somewhere from that conversation without having an agenda. You never want to appear like you have an agenda. Having an agenda turns people off to your whole conversation and ruins everything. But all of this conversational help, won’t do anything if you don’t have the real key to all of this.


A lot of things in the world are contextual. If you want to make friends, get to know people, have a spectacular life, you need to be able to grab a hold of opportunities as they present themselves before you. For example, if you have ever talked to someone at the bus stop or even just watched kids at the playground, creating friendships is contextual. The situation at the time dictates a lot of the interaction, so you need to be cognizant of what needs to be done. Some of the above techniques are less reliant on context than others (questions can be asked just about anywhere), but you should model your interactions based on the context of the situation. This is where things like timing, body language, the angle you walk at all come into play. Those are all important factors that you should not take lightly. The context may even allow you to skip most of these techniques altogether and just engage the person from the getgo in a conversation because you both have a shared experience together.

Anyway, for now, that’s all I have to say about this. But, there will be more coming later that goes into better ways to converse with people and the best way to keep the conversation flowing. Stay tuned!

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