Some Decisions Change You Forever

I used to be a nerdy gamer kid. Instead of shaking my ass at the club like a fish out of water, I stayed up until sunrise to slay Nofriends, Tormentor of Introverts in my mum's basement. But at one point, I realized life is more fun in reality than behind a screen.

Research shows engaging in positive social interactions with strangers can enhance your mood, increase happiness, and loneliness. An 80-year study by Harvard University found the quality of your relationships influences your happiness more than anything else.

To take my social skills to the next level, I committed to an experiment: Talk to at least one stranger every day for 100 days. The benefits were massive.

More (social) confidence
Improved conversational skills
Learned interesting things I never would've encountered otherwise
Beat my fear of rejection
Stopped caring what people think of me, which massively reduced my anxiety and set me free to be myself
Tons of new potential friends, dates, business partners, and cool experiences

Here's the good, the bad, and the ugly of how it went — and a few tips you can use to make it happen yourself.

You Don't Need Anything to Talk About

You can't get the nerd out of me.

Instead of just venturing into the wild lands beyond my apartment door, I set up a tracker to make sure I followed my commitment. Red "-" = no approach, green "x" = approach done.

A typical week in my tracker. | Screenshot by author

To make building the habit easy, I stuck to habit god James Clear's simple rule: Be specific. Every day during my lunch break stroll, I looked for one lucky soul to say "hey" to.

Then I tried to get a conversation going, usually starting with an observation or a question. It turned out much harder than I expected — but that's what made the successes taste even sweeter.

Now, I know what you're thinking.

"What would you even talk about?"

The answer is as simple as annoying — whatever you feel like.

Most people assume they have to say something funny, witty, or cool. No, you don't — at least not in the first place.

Instead, just be curious about the other person — what they're doing right now, their background, passions, expertise, dreams, plans, and sense of humor.

Keep this in mind and a simple conversation about the weather or weekend plans is all you need.

The First Step Is Always the Hardest (Week One of Approaching Strangers)

Everything you do for the first time feels a little weird.

Your first gym session, first driving lesson, and first time doing the naked tango. Approaching strangers was no different, but some situations 10x'ed the awkwardness.

I can hold conversations for hours with my friends, but when I rocked up to people out of the blue, my brain.exe crashed.

Many times, I chickened out. When I did it, the conversation went something like:

"Uh, yes, uhm, hey, hello, my name is… uhhh… potato?"

The only thing interrupting the awkward silence was my heart beating like Mike Tyson his punching bag.

But here's the good part — the more you suck at something, the quicker you improve.

The Bigger the Challenge, the Bigger the Learnings (Week Four of Approaching Strangers)

After a month, I had made massive progress.

I rarely chickened out. Because I wasn't in survival mode anymore, I could focus on making the conversation longer and steering it to interesting topics. More and more, I got past the five-minute mark.

When I started approaching people at the supermarket, bars, or gym parking lot, the behavior also felt more natural. This meant less resistance and more spontaneous conversations.

However, I still got the occasional awkward silence that made me excuse myself and leave.

Everything's a Habit If You Do It Long Enough (Week Ten of Approaching Strangers)

Science says it takes between 18 and 254 days to build a habit.

I hit it around the six-week mark. From then on, I no longer had to think about "Hey, I have to approach this person and say this thing." It just happened.

Habit expert James Clear calls this identity change — saying hey to strangers became a natural part of me.

This allowed me to focus on the other person and read them — are they comfy, are they interested, do they have a good or bad day?

Once the conversations truly flowed, I experimented with expressing different vibes and parts of my personality. I switched between the serious business guy and the relaxed dude who makes dinosaur-related jokes.

This was also when the conversations started to feel truly fun and I got good feedback from the people I was talking to.

Goodbye Anxiety and Overthinking (Week 14 of Approaching Strangers)

During the last few weeks, I fine-tuned my approach.

The only change I noticed was that I got better at warming up the people who weren't receptive in the first place because they had a bad day or said "Your face no me gusta."

I focused on staying in the conversation longer even if they gave me very little to work with. When I noticed it was time to leave, I did.

After nearly 100 days of approaching strangers, I noticed my anxiety and overthinking were gone — chatting someone up had become as normal as blowing my nose.

This Is What I Learned About Human Interactions From Hundreds of Approaches

A good friend of mine always used to say "Humans are funny." I agree. Here's what I learned from talking to hundreds of them.

Most people are just as nervous as you are. This means they worry so much about their appearance and behavior they don't have much time to notice you messing up.
If you don't make approaching someone a big deal, it isn't. The more approaches I did, the more casual they became. This made me realize connecting with others is one of the most natural things in the world.
You'll never regret approaching someone. I got some harsh reactions along the way, but I was always glad I pushed myself past my comfort zone.
Being open and interested is a cheat code for any social interaction. People love talking about themselves and their passions. Tap into it and they'll love you for listening to them.
Everybody can teach you something, your job is to find out what. I've learned so many cool things, new perspectives, and mind-blowing facts simply by being curious about the person.
Connecting with other humans makes everyone happier. Most people left our conversations with a smile, which made me happy, as well.

How to Make Talking to Strangers Easy

Holding a conversation with anyone is a skill that will open many doors and help you grow tremendously.

Here's how you can make it easy.

Practice, practice, practice. The more often you do it, the easier it gets.
Allow yourself to leave. Just because you say "hey" doesn't mean you have to stay in the conversation forever. You can always say "was nice meeting you" and roll.
Have a few questions and canned sentences to start. The beginning is always the hardest. Complimenting their clothes, asking for directions, or figuring out what they're up to can give you a head start.
Stop worrying about what they'll think of you. People are too busy worrying about themselves to remember for long when you messed up.
Don't beat yourself up if it's awkward. Cold approaching people is a tough skill — but a rewarding one.
Set mini-goals to keep yourself engaged. Say "Hey" your first ten approaches, ask for directions the next ten, and start a conversation about a random topic after. Climb the mountain slowly instead of breaking your neck.

This Is All It Takes

Learning to approach strangers has been one of the most beneficial skills I've ever learned.

It massively improved my self-worth, confidence, and social skills. It has opened more doors than I could walk through.

You can achieve the same.

Yes, it will be tough and awkward in the beginning. But it's a rewarding journey that will teach you more about life than you could ever learn from reading something online. So put yourself out there.

All it takes is a simple "hey."

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