Starting a Conversation with a Stranger

Starting a conversation with a stranger can be a terrifying experience. Your body walks towards the other person while your mind tells you to turn back. This situation doesn’t have to be scary. I’ve been the guy who stands in the corner the whole night, and I’ve also been the life of the party. Here are a few ways that have helped ease my discomfort and have fun when starting conversations with new people:


I get nervous before I start talking to someone I don't know. That feeling will never go away, but you can get better at handling the discomforting energy. Here's a situation that I've found myself in dozens of times:

Standing with my friends at a bar, I spot someone that I'd like to approach. I feel good, but what am I going to say? It has to be perfect. Maybe a comment on her hair? No. She's holding an old fashioned. I like old fashioneds. She's so hot, I 'don't know. She'll probably turn me down anyway. I'll save myself the embarrassment. Maybe I'll go talk to her after another drink. 

Then, you stand with your buddies, maybe stare at your phone, she leaves, and you missed an opportunity to make a connection. This mindset is death.

Here are some tips and tricks for approaching strangers that have worked beautifully in both my business and personal life:

This place reminds me of…

Can't think of something to say? Build a connection over a reminder. 

To do this, first, look around and observe the environment. Take in the bar, architecture, fashion, find something that sticks out. What does it make you think? 

Does the bar remind you of a spot you frequented in Italy? Maybe the texture of her earring sparks a childhood memory. Use this information to start the conversation. For example, walk up and say:

Your tattoo reminds me of a painting I saw last weekend. 

The layout of this place reminds me of a scene from Rush Hour 2.

The way they serve this drink reminds me of a pub I drank at in London. 

The reminder technique not only starts the conversation, but it provides a point of reference. Even the person says, "I've never seen that movie" or "I've haven't been there," you can jump in and tell them about your experience. 

Observe Something Unique.

This starter is straightforward. Most likely, this will be an exterior observation, like clothes or hair, as you know nothing about the other person.  

What is he or she wearing that nobody else or few others are wearing?

Observe color, texture, and unique patterns.

For example, you could say something like:

I noticed that you are the only one not wearing heels. I respect someone who values comfortability. 

Then, if she is interested, she will explain to you the decision to not wear heels, which will most likely be accompanied by additional information. Use her response as a launching pad to share something related and ask further questions. 


Research, Research, Research.

As a podcaster and content creator, I derive confidence from research. Before I sit down with a guest, I'll spend hours compiling information from past interviews, books, and articles.

I feel comfortable talking to a stranger on a podcast because I have dozens of talking points to breathe life into the conversation. 

So, I decided to take a similar approach when speaking to strangers outside of podcasts. For example, a few weeks back, I attended a rooftop party at a venue that used to be a tea factory.

Cool, right?

Before arriving at the rooftop, I researched various aspects of the factory and stored the most exciting pieces of information in the notes app on my iPhone. 

Then, when I spotted somebody I wanted to approach, I started the conversation by saying, "Hey, did you know this place used to be a Tea Factory?"

They all said, "no," and then we went on to have a conversation about the history behind the rooftop. Even if they had known it was a tea factory, you could still chat over the facts you've learned, a win-win. 

Don't try to be perfect. 

No perfect way exists to start a conversation.

Pay no attention to scripts pushed by supposed communication experts. What happens when someone says something off-script? You're screwed if you think that you can plan out a total, genuine interaction. But you can be prepared for the start.

To recap, you have a few places to start: the reminder, a unique observation, and a topic of research. Creativity unlocks limitless opportunities for starting points.

Be confident, be direct, and most importantly, listen to what the other person has to say.

The best way to be interesting is to be interested.