I Talked to 1000s of Strangers—Here Are 9 Valuable Conversation Tips
Trust me: If I can do it, you can too.
I always get a kick out of conversation advice from exceptionally beautiful people.
It’s like, are you bloody serious? You could say anything and get a decent reaction.
But ya boy wasn’t blessed with good looks, height, or an ethnicity that was en vogue in my home country. I even had crippling acne for years—and yet I still figured out how to talk to people when I had breakouts.
So if I can do it, you can do it too.
Below, I’ll share 9 of my best tips for people who want to improve their conversation skills and unlock all the benefits that come with it.
Don’t try talking to everyone
Not everyone wants to talk to strangers—accept that.
Not everyone wants to have conversations—accept that.
As much as I love having conversations, when I want silence, I dislike when people talk to me—and they cannot take a fucking hint.
Before you talk to anyone, assess the situation. Do they look friendly? Do they look kind? Do they have their shields up? Do they seem like they’re dripping with attitude? Do they seem busy or stressed?
Most of your success happens before you utter a word. Read the situation first. That way, you’ll skyrocket your odds of a good interaction and reduce any possibility of a bad situation.
95% of your success is on you
If you don’t have a great attitude or mindset, you will struggle.
I’ve talked to thousands—literally thousands—of random people and my results almost always come down to my own beliefs or feelings.
For example, when a man approaches a woman, if he conveys subtle signs that he expects failure—or that he won’t do well—the woman can tell 99% of the time.
He’ll be tense, show subtle signs of fear and insecurity, and get stuck in his head (which causes people to go blank and “run out of things to say”).
And he will fail.
The opposite is true. If someone has a great attitude, feels positive, confident, and like they’re having fun, the results are almost guaranteed.
If you had a poor interaction, review what happened and assess how you could’ve improved. Bad eye contact? Bad mindset? Stiff body language? Too scared? Approval seeking? Not asking enough questions (or asking too many questions)? Constantly talking about the same topic without switching?
It all comes down to you.
Play to your strengths
Recently, I saw a guy walking down the street and wave to a woman who was sitting by the window of a coffee shop that I was in.
He walked in, introduced himself, kissed her hand, spoke like he was reading a romance novel, felt her chakras and vibrations (seriously), and strongly looked into her eyes like he was trying to hypnotize her.
I ain’t hating on that, though—it worked for him and I admire his courage.
But that is not my style. And I would never teach that because I don’t do that.
You have to do what works for you. You have to play to your strengths.
Are you a bold and larger-than-life person? I know people like that. They can do those types of things—talk to a large group all at once, draw lots of people in, etc.—and it fits them very well.
I’m a quieter, introverted-leaning person. I’m more of a calm cafe, bookstore, or event type of person who talks one-on-one to similar people.
If we reversed our environments, we might be able to make it work, but it wouldn’t fit seamlessly.
Use your personality to your advantage.
I’ll get to that more below.
Be observant
When I worked at a gym, I hated talking to gymgoers because I didn’t want to interrupt their workouts. I also had little context to start a conversation.
But I’m a massive sports fan. So if someone was wearing a hat or shirt from a team, I could easily spark conversation—and it felt very natural.
Sports is my niche. What’s yours?
Music? Comics? Movies? Watches? Languages?
Use it! Look at a person and you can spot little details you can talk about. Their shoes. Their shirt. Something they said. Their accent. A tattoo.
Get them to talk more than you
I’ve been on a lot of dates and I would say the most-common conversational problem I encounter is that the other person doesn’t ask anything about me. Like, one or two questions in an hour. (It doesn’t last longer than an hour because, by then, I’m ready to leave.) Or if they do ask a question, within seconds, they interrupt me and make it about themselves.
But genuine interest could be the single best trait in conversations. Ask questions. Be curious. Be fascinated with the other person.
Over the years, I’ve even ditched “friends” who literally never asked anything about me whenever we had conversations. (I called them out on it and it unearthed a lot of issues lying underneath so don’t ignore this red flag.)
Similar to this, a lot of people talk too much. They “overshare,” say everything that they think, and try too hard to be “cool.”
A very simple rule is to make sure the other person talks more than you. That way, you’re guaranteed to listen and avoid talking too much.
Think like a standup comedian
The late, great Norm MacDonald (who I miss dearly) once had Jerry Seinfeld as a guest on his show. Jerry told a joke that Norm’s partner laughed at, but didn’t actually understand.
Norm then said, “I knew you didn’t get it. I can spot a fake laugh from a mile away.”
Of course, he can: Norm was a legendary comedian.
He knew immediately when people thought something was funny or not.
Standup comedy is as results-based as it gets. It doesn’t matter how famous a comedian is; if their jokes aren’t funny, people won’t laugh.
Conversation is too. If you’re doing well, you'll feel it. If you’re doing poorly, you’ll feel it. After a while, it doesn’t matter how tall, sexy, or whatever you are—if you suck, you’ll suck.
Be honest about your results and improve what you can. Do your conversations flow better? Do you feel more comfortable and relaxed? Is the other person more involved? Do they follow up and exchange information?
Always aim to get better.
Forget about what others do
Here’s a funny thing I noticed from people who ask me about conversations: They assume that everyone else is going around and having brilliant conversations all day long and masters at this.
That is categorically false.
If anything, people are increasingly socially awkward these days.
Don’t worry about others. Don’t worry if you’re not perfect. If you’re enjoying yourself and having a good time, that’s the most important thing.
Dress correctly
I’m not going to bullshit you: If you dress like a slob, it’ll be hard for anyone to be receptive to talking to you.
You don’t need to dress like a runway model. Just wear clothes that fit and match the occasion. As Tom Ford said, “Dressing well is a form of good manners.”
If you want to have better interactions with strangers, dress like you care about yourself.
You might even notice that more people start talking to you.
Start small and work your way up
Okay, so now you’re excited. You learned all these great traits and you’re ready to try to talk to every single human being you come across.
Slow down there, homeboy.
That is a recipe for disaster. You’re going to hate it after a while and it’ll be so stressful, you might just scare yourself out of it.
Start small and work your way up.
Unless you live in a cave—or a remote village—you have the opportunity to have brief interactions every single day (or at least a few times a week).
Take advantage of them.
Talk to your barista. Talk to your colleagues from a different department. Talk to the clerk at a store. That’s what they’re there for.
Get used to having 20–to-30-second interactions and feel more confident talking to people you don't know. You’ll feel more comfortable and make faster progress when the stakes are lower.
You’ll also build more confidence, which will translate to better results no matter the situation.
Hope it helps.
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