30 Tricks You Can Steal From Social Butterflies for Approaching Anyone

How to Approach People

Written by Ivan Chan

It’s terrifying approaching someone for the first time.

Naturally, you want to make a good first impression with this person, but you have no idea how they will react to you. Will they like you? Will they reject you? Will they think you’re an idiot?

The fear of looking like an idiot by saying or doing something stupid is uncomfortably real. Maybe you have had it happen in the past. The thought of having it happen again is making you nervous about approaching someone.

I used to be terrified of approaching people too.

I would sheepishly stutter my way though an introduction. I would make futile attempts at small talk, only to flounder awkwardly. After enduring much frustration, I eventually stopped trying. I figured you couldn’t get hurt if you just watch from the sidelines and avoid putting any skin in the socializing game.

That’s not a fun way to live.

After all, a wealthy life is not just defined by how much money you have. It is also defined by how rich your relationships are with your friends and loved ones. Every relationship starts with you approaching someone whom you’ve never met before or the other way around. But most people don’t have the courage.

I decided to work on my social skills. They don’t teach you how to approach people in school, so I learned from others whenever I could and experimented. I tried different ways to make a memorable introduction, to keep people engaged, and to leave people wanting to come back and talk again.

It took me years, but I eventually found a system that works–a system I’ll share with you today. So grab a cup of coffee and make yourself comfortable.

You’re about to learn how to approach a stranger with confidence, charisma, and even a little flair. These techniques will work regardless of whether you’re at a professional event or a hot singles’ party.

Are you ready?

How to Approach PeopleFirst step? Don’t do that to strangers.

How to Approach Anyone

1. Tackle approach anxiety

Are you deathly afraid of approaching people? If so, then you may a bad case of approach anxiety. As with most fears, the way you conquer approach anxiety is to desensitize it.

How to Deal with Approach Anxiety

2. Get in the right mindset

You’ve decided to approach. Are you feeling a little nervous right before? Take 10 deep breaths to calm your nerves and tell someone to shut up.

No, not a stranger. Tell yourself to shut up. Don’t listen to your lizard brain or your fears.

You have to get in the right mindset.

That is, you shouldn’t treat other people like a total stranger. If you want to have a fun conversation then act like you’ve known the other person your whole life. It will lead the interaction with the right vibe.

Also, think of your conversation as a chance to make the other person feel good about themselves.

Treating Strangers Like Friends

3. Channel your inner storyteller

Some more pre-game.

You need stories ready to make the conversation interesting. They don’t have to be dramatic or funny. But they should serve as fun conversational starters. That way, you’ll have something to fall back on when conversations turn into a lull.

The Science of Storytelling: Why Telling a Story is the Most Powerful Way to Activate Our Brains

The Art and Science of Good Story Telling

4. Shake hands

You’re going in now. First off, shake their hand. Firmly, not with a dead fish grip.


Make sure you don’t have sweaty palms. I used to have the worst case of sweaty palms in high school social dance classes. You can imagine how those felt for the other person.

A Manly Handshake: An Illustrated Guide (Works for women too)

How to Treat Sweaty Hands

Sweaty Palms and Feet: Coping Tips 

5. Remove the voices from your head

You’re in. You initiated, but you’re starting to become nervous.

How many times have you started a conversation, feel weird, and try to exit as fast as possible? If your answer is zero then I bow down to your smoother-than-James-Bond socializing prowess.

The rest of us make excuses when we’re afraid. Tell your excuses where to go. Kick them out of here. You can pull through anything.

6 Valuable Lessons a 19-Year Old Learned From Reaching Out to Millionaires

6. Think like an economist

Opportunities in life come and go. In my personal life, the biggest regrets I have are not from things I have done. Rather, my biggest regrets are from things I could have but did not do.

Will you regret it if you don’t muster up the courage to approach that certain someone?

What Happens When You Get Stuck Wondering What If

7. Remove your serial killer look

Obviously, you’ll scare someone if you don’t. People are naturally wary about meeting a stranger at first. The way you ease their wariness is to have a relaxed smile that seems natural, not with a serial killer grin.

How to Smile

Ron Gutman: The hidden power of smiling

8. Remember that you’re not auditioning for a play

You don’t have to start a conversation in a witty way in order for it to be memorable. Don’t memorize lines. Just start with “Hi!” and you’re good to go. Of course, as you become more comfortable with strangers, you can add more flair to your bantering.

Remember: the more you think, the more difficult it becomes.

The Value of Bantering

9. Never forget another name

Always, always, ALWAYS pay attention when the other person introduces their name. Obviously, most people take their name very personally. So remembering someone’s name correctly will no doubt leave them with a good impression of you.

Dale Carnegie famously said that a person’s name, to that person, is the sweetest and most important sound in any language. Think of how you feel when someone remembers your name towards the end of a conversation. Feels pretty good, doesn’t it?

How to Never Forget the Name of Someone You Just Met: The Science of Memory

10. Give out genuine compliments

You can be personal by offering a sincere compliment. People like to feel liked.

Remember, sincerity is key. Fake compliments are pretty obvious and even insulting.

Quick tip, comment on something they put effort into. Complimenting them on something out of their control isn’t as warming as something you noticed they did.

The 12 Characteristics of Great Compliments

11. Take compliments with class

So, you can dish out compliments, but can you take them? A conversation is a two-way exchange. Show your classy side when you’re on the receiving end of a compliment.

Don’t downplay them. Don’t deny them. Just say “thanks.”

How to Accept a Compliment with Class

How do I accept compliments?

12. Empathize and relate to build a connection

Having gone through university myself, I understand how stressful exams times can be. I often use this as a way to empathize with students who are currently going through exams.

Showing someone you know how they feel makes them more comfortable to talk with you.

Six Habits of Highly Empathic People

13. Keep your ears open

I know this advice sounds obvious. But then how come so many people absolutely SUCK at listening? It’s sad but true. So if you train yourself to be a skilled listener, you’ll no doubt instantly standout among the crowd. Listen more often than you talk.

How to listen

Active Listening

14. Make them feel good with great questions

So what happens if you’re at a conversational standstill and none of the techniques I’ve discussed so far is working? Ask awesome questions! People love talking about themselves, after all.

How to Be Amazingly Good at Asking Questions

10 Tips for Asking Good Questions

15. Take the lead

What does being a good ballroom dancer and being a good conversationalist have in common? You have to know when to lead and when to follow in both situations. So, lead!

Techniques to Steer a Conversation

Control Answering of Questions

Initiate new topics

16. Keep your mouth in check

It’s tempting to think that the world revolves around us. Not surprisingly, a lot of people talk about themselves non-stop because it feels good to them. However, being a good conversationalist means talking less and listening more. So don’t be a conversational narcissist.

Let others have a turn.

The Art of Conversation: How to Avoid Conversational Narcissism

17. Avoid being a pretentious “one-upper”

I once worked with someone who always had to one-up whatever you say.

He always wanted to have a bigger and better story to tell than everyone else. Talking to him gets annoying really quickly. Don’t be that guy.

How do I stop ‘one-upping’ people?

18. Accept that you’re not a genius

If you don’t, then sooner or later people will realize you’re just a fool desperately trying to look smart. If you don’t know something, just admit it. Most people will be glad to explain. That way, you’ll actually learn something (and end up being smarter for real).

How to Ask for Help Without Looking Stupid

19. Remove your habit of judging

Take my blogging mentor, Jon Morrow, for example. Jon has spinal muscular atrophy (SMA). He can barely move his body from his neck down.

Based on appearance alone, some people might be surprised to learn that Jon is the Associate Editor of Copyblogger.com, a highly successful entrepreneur, and an all-around badass.

Judging People by their Appearance – A Wrong Step Forward

20. Know what topics get people to want to murder you

Nothing kills a conversation more quickly than an ill-advised tangent into an icky topic. You have been warned.

10 Topics to Avoid When Making Small Talk

21. Get rid of your habitual filler words and phrases

By filler, I mean the “umm’s” and “ah’s” people utter when they’re trying to think of something to say. Then there’s the dreaded “like” filler, as in, this is, like, the most annoying filler, like, ever!

How to Stop Saying the Word “Like”

Becoming Well-Spoken: How to Minimize Your Uh’s and Um’s

22. Leave interrogation to the police and interview questions for hiring managers

Remember how I said you should ask really good questions to direct a conversation? It’s a good strategy, but don’t overdo it. If you barrage someone with too many questions, they will feel like you’re interrogating them.

Mix up your questions with some non-questions. Better yet, expand on the conversation based on what you’ve heard from the speaker to show you’ve have been paying attention all this time.

How to use statements to get someone talking back (aka questions are for wimps)

23. Reminder yourself that pauses are normal

I used to worry about what to say whenever there is a pause in a conversation. I’ve since learned pauses are OK.

Admittedly, it feels a lot less awkward being in silence with a close friend than an acquaintance you have just met, but don’t worry, there are ways you to end the silence quickly and restart the conversation.

Ways to Deal with Awkward Silences in Conversations

How to Fill Awkward Silences

24. Stop interrupting, it’s rude

Have you ever had someone blurt things out before you’re done talking? It’s annoying, right? So don’t do it yourself. Avoid interrupting others when they talk or you may kill the conversation.

Why People Interrupt (and what to do about it)

25. Be conscious of your body language

Seriously, you should do as your Mother have told you a long time ago. Stand up straight. Don’t hunch forward. Bad posture is just so uncool and unsexy.

Great posture automatically makes you look more attractive, interesting, and self-confident.

The Ultimate Guide to Good Posture

Better Posture: 6 Ways to Straighten Up

26. What are you doing with your hands?

Yes, we’re back talking about hands again. This time we’ll talk about where to put your hands while you’re talking. Your body language says a lot of things about you.

You may think your words are wowing your listener, but if your body language is conveying a different message altogether from your words, then you’ll be fighting an uphill battle for the entirety of that conversation.

Your Hand Gestures Are Speaking For You

What Not To Do With Your Hands (When Speaking)

27. Stop looking away, give them your focus

Smartphones have somehow managed to connect people like never before while simultaneously destroying face-to-face communication.

How often do you go into a public place (e.g. a train or a park) and find virtually everyone in sight to be thumbing away on their phones? In the age of rapid digital communication, it’s the simple look-them-in-the-eye conversation that is bound to be memorable.

Look ‘Em in the Eye: Part I – The Importance of Eye Contact

Look ‘Em in the Eye: Part II – How to Make Eye Contact the Right Way in Life, Business, and Love

28. Slow down and don’t lose them with your words

As Michael Caine once said, “The basic rule of human nature is that powerful people speak slowly and subservient people quickly–because if they don’t speak fast nobody will listen to them.” Are you powerful or subservient?

Social Skills Teardown – Talking too Fast

29. Test out different vocal inflections

This is, once again, another obvious-sounding advice, but how obvious is it really? I know many people who speak as if they are unsure of everything they say.

One way you can tell is they tend to raise their voice at the end of a phrase, the way you would with a question. Only instead, they do this with EVERY SINGLE STATEMENT they say. It’s as if they are asking you for permission to speak.

Three steps to conquering the “up-ending sentence”

How to Make Conversation with Confidence

30. End your conversation on a high note!

All great things must end. And sadly, that includes your lively chat with the lovely person in front of you. But don’t go out with a whimper! Like all great things, you should go out with a bang (and leave them wanting more).

How to End a Conversation

End A Conversation: 4 Steps

The Floor Is Yours

You’ve got all the know-how.

You’ve learned all the tricks.

You know what you need to do next?

It’s one thing to be an expert in the theory of knowing how to approach people. It’s a different thing completely to be an expert IN approaching people.

The only way you’ll get good at approaching people is if you, well, practice approaching people! That’s how I did it. That’s how everyone does it. That’s how you’re going to do it.

Just pick one or two things above and start practicing. I know it’s going to be hard at first. But in time, you’re going to get better. I’m sure of it.

So what are you waiting for?

Photo Credits: Dave Fayram, Flickr and Ed Schipul, Flickr

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Ivan Chan teaches professionals how to make smart money decisions that fit their lifestyles. Unfortunately, it looks like the website he used to run is no longer up.

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46 responses to 30 Tricks You Can Steal From Social Butterflies for Approaching Anyone

  1. Sometimes the best way to remove filler words is simply to speak a bit slower. Taking your time and formulating every sentence. I have tons of stories and I’m quite comfortable taking control and speaking slowly and clearly, but I need to ask some more questions and spend some more time just listening..

    Thanks for the tips man.. have a nice Monday!

    • That’s something that I didn’t understand for a long time. When I got excited I would speak SUPER fast and I still remember the reactions on some people’s faces. Not good reactions either!

      • I hear ya, Vincent! I’ve gotten quite a few of those looks myself in the past as I used to speak really fast.

        Funny how speaking slower can make us sound “dumb” in our heads when in reality it’s making us sound more confident to everyone else!

    • Hey Ragnar! Great to hear you’re comfortable telling stories at a slow and comfortable pace. Not many people I know can do that well so kudos to you!

      As for taking the time to listen, I have a rule that I’d try not to talk about myself until I’ve given other people a chance to talk about themselves. You can do this by leading the conversation with good questions. Works every time!

      Thanks for your thoughts! Have a great Monday too!

  2. Thanks for a wonderful guest post, Ivan! Pleased to have you back on here. 🙂

  3. Good article Ivan. The trick I learned based on my own experience of going out and approaching people is this – ‘You MUST get the other person to invest’

    The secret to becoming attractive is that a person needs to invest in you. The more they invest, the more attracted they will be towards you because us humans naturally value the things we work towards and value it a lot more.

    It’s the reason bantering works, particularly with girls because it provokes an emotional response which in turn gets them to qualify themselves to you and invest 😉

    Of course, it’s easier said than done. We need to get over approach anxiety first, but beyond that, it’s all about getting them to talk.

    • Thanks, Onder!

      You make an interesting point on getting the other person to invest in you. If they do, then yes that would most likely make you seem more attractive.

      That takes time and patience though. And I find that usually only happens after you’ve first shown genuine interest in the other person (i.e. with no hidden agenda). So be patient and keep up your efforts! 🙂

      • Thanks Ivan.

        There are a lot of variables in order to break it down. Like for example, for someone to invest in you, they need to ‘value’ you enough to want to invest in you in the first place.

        So if you having something that the other person needs, they will naturally invest in you anyway with little work from your part.

        Otherwise, you will need to add value first by displaying attractive qualities that girls want – Good Physique, health, wealth, hobbies, confidence

        Approaching girls gave me a massive realisation of my own value and made me realise what I need to work on. In short, the hotter girl is in comparison to you. The more value you’ll need to build and provide in order for her to want to invest in you.

        This principle is universal, from applying to jobs, building a popular blog and becoming an authority figure.

        A few things to think about. 🙂

        • Ah yes, very good points. Providing value to others is definitely a sure-fire way to get people to notice you. Of course, exactly what is valuable depends on the situation. But the general principle of being generous and helpful to others stays the same no matter what.

  4. What a really through list. I was trying to think of something to add here, but I think you’ve covered it all. Like you, I used to be afraid of going up to people and starting up conversations. It can be nerve wracking if you’ve never done it before. In fact, it still can be nerve wracking.

    Something I’ve learned a while back is that if you’re at a party and you want to start up a conversation with someone, you just have to do it. Don’t think about it, just do it. The first time is always the hardest. Once you’ve done it that first time, it becomes easier.

    • Steve, I too still get nervous whenever I’m approaching someone. I guess that feeling never quite goes away. And I agree: no matter how scared you are, you still need to do it!

      In fact, the more nervous you are approaching a particular person, you more you need to approach them. We get scared usually because something is on the line, be it our egos, a potential hot date, or an awesome business opportunity.

      Your fears are showing you where you need to grow. We both should remember that the more we practice approaching people (and facing our fears), the easier it gets!

    • I worked with someone named Andrew Elsass who spent a month with one goal in mind: approach at least 3 different people each day. I’m going to make a case study on it and include it in my eBook. A lot of interesting findings and realizations that would shed some insight into approach anxiety. 🙂

      • Wow, what Andrew did sounds fascinating! I imagine the hardest part is just to get started. I know that’s the case with me. As soon as I get over talking to that first person, approaching anyone else after that always seems like a breeze.

  5. Damn you took us through the whole interaction. That’s awesome man.

    I resonate with so many of these points. I went through a very similar journey of feeling scared and introverted and then turning into a socially confident person.

    Your point about “one-upppers” is really awesome and not talked about that much. I know someone in my own life who does this shit all the time. Obviously it’s coming from a place of insecurity and a feeling of never being good enough. It’s just great to hear someone talk about it 🙂

    Killer post man.

    • Thanks for the kudos, Kevin! I thought I’ll do something more than the typical post and walk through the WHOLE approach point by point. I’m glad you like it!

      So you’re an introvert too, hey? Me too! Being an introvert can be hard in social situations, especially when everyone seems to be outspoken and interacting with everyone else (except you). I certainly know what that feels like.

      Great to hear you’ve went on a similar journey as me to transform your social skills. We’ll have to compare notes some time!

  6. Hey Ivan is there any reason the links aren’t working for me? thanks

    • That’s really weird because the links seem to be working just fine. I’m checking out the stats and it looks like others are clicking through as well. Are all the links broken on your end?

  7. Wow, great list of solid tips. I especially like the one about staying away form topics that make people want to murder you. Good sense of humor. But really, well written article. Thanks.

  8. Ivan,

    What a great list of solid tips here! I am not a naturally outgoing guy, but I have been forcing myself to use a lot of these for quite a bit of time. Things like active listening and using people names are a wonderful way to really connect with strangers and make an impression that will last.

    Love the list and all the links to what seems to be some interesting background material!


    • Thanks, SJ! I’m glad you found this post useful!

      Keep up the active listening and using people’s names. Too many people don’t do that these days so you’ll standout just by making the effort on these “little” things.

  9. Thanks for all of these tips. I used to be very shy and really awkward in social situations, especially going to a social gathering alone. I have gotten a lot better at making conversation. But I typically get into a really long, interesting and meaningful conversation with one or two people. So the title of this post is interesting when it refers to “social butterflies.” I definitely don’t know how to move from person to person for short interactions. I’ll check out the links on ending conversations.

    • You’re welcome, CJ! Moving from person from person is a real art and definitely takes practice.

      Yes, definitely check out the links. At the same time, do realize there is NOTHING wrong with having deep, meaningful conversations with just one or two people at a party.

      While it’s fun to move around and meet everybody at a party, it can be just as fun to really connect and have a select few people remember you long after the party has ended!

  10. For me, it was all about approach anxiety. Once I learned to stop listening to the little voices inside my head I was much better off. I wasn’t afraid of talking to people, I was afraid of approaching them.

    • Way to shut off those little voices, Don! Approaching people is easily the hardest step in getting to know someone. Once you’re past that, everything just seems to get easier. 🙂

  11. Now I just hope I don’t have a serial killer look…will have to watch that one.

  12. Well said! 30 tricks is a lot but I appreciate most #12 (Empathize and build a connection) as I have developed this habit and seems to work well in making a conversation with ease- that is, when you talk about commonalities between you and the other party.

    • Definitely, Rob! So many people dominate conversations with only what they want to talk about. And then they wonder why other people tune out after a few minutes.

      But if you focus on what you and the other person have in common, they’ll be interested every single time!

  13. This is the most helpful article i have read in a long long time, maybe ever! Thank you so much!!!

  14. Hello, do you allow guest posting on selfstairway.com ? 🙂 Let me know on my e-mail

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