How To Go From Small Talk To Deep Relationships

I love those beautiful nights under the stars, engulfed in conversations about life, purpose and love. When time stands still and the only thing that exists is the connection between you and the other person.

Those are the connections that I live for.

I think everyone has that deeply beautiful side to them, just waiting for someone to reach out and connect to it. Sometimes I just want to walk up to a person and ask them about their dreams, the things they are afraid of and the disappointments that have forged their character.

I want to know every detail about them, the good, the bad, and the ugly. I love that imperfectly perfect image that you discover as you chip away the walls that we build so high.

But you can’t connect to someone on that level right away. You need to start somewhere and build rapport, and there is only one way to do that.

Small Talk

Anyone that knows me well enough knows that I hate small talk. I don’t like all the fluff that surrounds it.

“Wow, the weather is really terrible today, right?”
“How about X sports team, they’ve really been doing badly, right?”

Maybe it’s just me but I don’t really care about that kind of thing, and two people talking about things that don’t interest them, excite them, or reveal any of their beauty makes for a pretty mundane experience.

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But, since small talk is never going to go away and is necessary for building a relationship, I’ve decided that I will make it my goal to have the best small talk experiences and transition to real conversations as quickly as possible.

Once you build rapport you can start to relate to a person and explore who they really are. That is where real relationships are forged. That is where you find the people that you can call crying at 2am, the people you can rely on during the good and the bad.

So this is my guide to getting through the small talk as quickly and gracefully as possible, allowing real conversations to flow and real relationships to be cultivated.


I was going through the motions with a customer when he stopped me.

“What’s your name?”
“Oh, It’s Steven.”

And from that point on he used my name in every other sentence. The conversation was amazing and I felt like I had known him my whole life by the end of it. There was a certain warmth to the whole exchange that made it feel that much more real.

Everyone knows that when you meet someone the first thing you should do is introduce yourself, the part where most people fail to capitalize is that they are just going through the motions. Most people don’t even remember the names of those that they engage in small talk with.

When you introduce yourself make sure that you remember the persons name and use it throughout your conversation. People love hearing their name and it creates a sense of familiarity that is essential in transitioning from mundane small talk to anything bigger.

Another thing to keep in mind is that after the introduction people usually never hear your name again, so it’s easy for them to forget it. If you can, mention your own name more than once throughout the conversation so they have a chance to convert it to their long term memory.

You can do this two main ways:

  • Address yourself by name. For example, “So I thought to myself, ‘Steven, you have got to get better sleep.'”
  • Use your name in dialog. For example, “So my friend said to me, ‘Steven, you have got to get better sleep.'”

If you remember their name while helping them to remember yours, you will have a much better chance of leaving a lasting impression and deepening the connection.

Ask Questions

The second way to ensure that you build a real connection and avoid being stagnant in small talk is to ask questions.

We love our names, and we also love talking about ourselves. It’s understandable, we know ourselves better than any other subject so it comes naturally. When we ask someone about themselves it makes them feel important and interesting.

A real interest in other people is the best gift that you can give them. Too many people only care about themselves and it ruins a lot of potentially beautiful relationships.

Whether it’s deeply revealing questions or just your basic small talk questions, you should always keep in mind the 5 W’s. (And the one H)

Who, what, where, when, why, and how.

Whenever someone makes a statement you can build the conversation off of it by asking a question that gets them to reveal more details about their statement.

If someone mentions that they went to a certain university you now have the ‘where’ and ‘what’ but you can still ask them why they chose that university, how they got along there, or when they started.

When you keep those 6 questions in mind you can always slip one in to continue the conversation and reveal a little bit more about the person.

Another thing to keep in mind is that you should avoid questions that have one or two word answers. If you get a short answer, ask a follow up question and continue exploring the details.

Offer Compliments

You might be noticing a trend by now. Having productive small talk that actually leads to a real relationship is all in making the conversation about the other person.

We say their name to create familiarity and make them feel important. We ask them questions to make the conversation flow better, since we are all experts in the subject of ourselves. And we should also offer them compliments.

There is nothing more powerful than a real compliment and there is something to be noticed in everyone.

My general guideline for compliments is that I try to avoid anything generic. It is always better to give a compliment that you actually believe. Also, I usually like to break my compliment into two statements, first I introduce the compliment and then I detail it.

“You are honestly such a positive person. It’s so nice to see someone with such a genuine smile on their face.”

A real compliment can go a long way in cultivating a connection with someone.

The saying goes, “If you don’t have something nice to say, don’t say anything at all.” But I have always preferred my own version, “If you have something nice to say, you have to say it.”

Mirror Them

People feel more comfortable when they are talking to someone who reflects their mannerisms, tone, talking speed, and general energy levels.

It helps to cultivate that feeling of familiarity and give the impression that you are both on the same page.

While you should follow your partners lead to make them feel comfortable, don’t copy everything they do down to the T.

If they are calm and relaxed, and you are chock full of energy, there won’t be any cohesion in your conversation.

Match their general vibe and the conversation will be smoother and overall more enjoyable.

Hopefully with these tips you will be well on your way to having small talk that actually leads to something instead of being a stagnant dead end.

I still dream of the day that I can walk up to someone and immediately have those amazing discussions about life, love, fear, ambition, and all the other things that make my heart beat a little faster.

But until then, let’s take our small talk from being a chore, to being a door to something beautiful. Because we all have that beauty inside of us, we just have to get comfortable enough to let it out.

Thank you for being a part of this beautiful conversation, I love you all.