How to Be Awesome at Approaching People

silhouette conversationToday, you’re going to get a lesson in social interactions from my personal relationship/dating yoda, and one of my favorite people on the planet, Lindsay Miller.

I met my friend Lindsay my freshman year of college and I have been going to her for advice when it comes to life, love, friends and dating ever since.  She’s so good at this whole human relationship/social life thing that she actually started her own TV show at Vanderbilt called SexRx, in which she helped college students sort out their love lives.

The show was so popular that even though Lindsay graduated and left Nashville years ago, SexRx is still a Vanderbilt TV staple and airs episodes weekly.

I asked Lindsay to put together an article today about leveling up your social life, a topic we can certainly look at more closely here at Nerd Fitness.  Considering one of the most popular articles of all time on the site is “5 Ways to Instantly Appear More Confident,” I’m guessing we have a lot of Rebels who could benefit from a primer on social interaction!

Don’t worry, we’re not talking about any shallow “Pickup Artist” seduction techniques.  Instead, we’re going learn to casually approach and talk to people! Regardless of whether you’re married, single, or in a committed relationship, there are tons of lessons you can take away from today’s post.

Take it away Lindsay!

How to level up your social skills

Level Up Social Skills

Hi, I’m Lindsay, and I think being comfortable talking to people is an important skill. Why?

  • For starters, there are lots of them. Seriously, people are everywhere these days. Sometimes they want to talk to you, and it’s rude to run away screaming.

  • They may be able to help you with things.

For these and many other reasons, I think we can all agree that if we had to choose between being awesome at approaching people and being horrible, we’d like to be awesome.

Today you’re going to learn how.

This is the first in a series of articles over the next few months about being awesome in your interactions with other people, whether they’re coworkers, strangers on the street, or that girl/guy you’ve had a crush on for weeks. You’ve already been hard at work leveling up your life by improving your diet and physical fitness.

Now you’re going to put it all together and level up your social skills.

From awkward to awesome

Group of Feet

I speak to you now as a super-confident manslayer, from humble (and nerdy) beginnings.

My social peak was probably at age four, when my freestyle interpretive dance to Paula Abdul’s “Cold Hearted” brought an entire wedding party to a hushed standstill. From there I entered something of a crushingly awkward period (ages seven to seventeen) where most of my social interaction was comprised of looking in longingly from the outside. That lasted until I figured out that I wasn’t all that shabby looking if I stood up straight and hosed some of the dirt off. I’ve never looked back since.

From then until now, I’ve made it my mission to help people find their voice and connect with others.

Steve is to deadlifts what I am to first dates.

My goal is to help you do in ten minutes what it took me ten years to accomplish, because nobody should be stuck on the outside looking in.

Alright! Let’s get awesome.

Whether you’re extremely shy about approaching new people or you’re already at ease, this is a skill you can never practice enough. Like everything else Rebels do, today we’ll have multiple levels of tasks (three), in order to get you more comfortable talking to people:

  • The Inception
  • The Drive-By Compliment
  • The Question Mark

Level 1: The Inception

Inception Social Skills

This level is all about the thoughts you want to implant in people’s heads.

Metaphorically speaking, of course.

Just like all your other self-improvement goals, the more specific you can be about what you’re hoping to achieve, the better. Take the time to give your goals some bones, some structure—it’ll make it that much more satisfying when you achieve them.

Who are you interested in approaching? A potential boss? A potential date? Someone at a party who could be a cool new friend? The more you flex your social muscles, the more comfortable you’ll be across all dimensions. Considering this beforehand is important to note the ways you might want to tailor your approach to different audiences.

What sort of impression do you hope to make on this person? What do you wish he or she would say about you afterward?

Think about the people who have made a great impression on you recently—what was it about them that made you say that?

This exercise is useful because it helps focus your attention on the little, specific things that make such a big difference (like remembering people’s names, smiling, and maintaining eye contact…ideally of the non-creepy variety).

What are you most confident in already? When people compliment you, what do they tend to say? This exercise is great because as you try to stretch yourself socially, and you find yourself in positions that might give you a butterfly or two, it’s great to call upon your existing strengths for little boosts of confidence.

For example, if people have complimented your laugh, you could remind yourself that: “I’m a happy person. People notice that and enjoy being around me because that feeling is contagious.”

Or if you’re good at video games, you could think, “I can handle a lot of information at once and think on my feet, and people will appreciate that I can make decisions quickly and confidently, and have fun doing it.”

Look at that! You’re done with Level 1 already. Let’s keep it up.

Level 2: The Drive-By Compliment

Compliment U ROCK

This is pretty much my favorite thing in the entire universe. It’s extremely high payoff with zero risk, which, according to my business school classes, is technically supposed to be impossible. You ready?

What’s the biggest concern that you have in approaching other people? Being blown off? Being seen as a bother? Making a fool of yourself? As someone who has been blown off, seen as a bother, and made a fool of countless times, I’m not going to tell you that it never happens, or that it shouldn’t get to you. I’m just going to give you the antidote.

Say something nice to someone. Anyone. As many different people as you can.

Seriously. Strangers. Old, young, male, female, alone, in groups, whatever. I want you to be a compliment sprinkler, watering the lawn of the people around you with drops of good vibes. Or something. Here are some sample sprinkles:

  • Cool boots!
  • What an awesome dog!
  • You have a great smile.
  • Those jeans are cool.
  • Neat shirt!
  • You’re so lovely!
  • You have a great laugh.
  • I like your Trapper Keeper.
  • You look so nice today!
  • You look so happy!

 You make eye contact (this is important!), say one of these things (really say it, don’t just whisper it conspiratorially as you sprint past them), and then… you vanish. That’s it.

 Let me take you through a brief tour of why this is so amazing. First, and most crucially, you cannot be shut down, because you’re not putting anything out that could be shut down. Secondly, you’re not asking for anything, nor are you even asking anything at all, so there’s no risk of being blown off—no question left awkwardly hanging in mid-air (you know, like this). And finally, the people on the receiving end of these drive-by compliments will be caught off guard in the most pleasant way. They’ll either respond with a genuine “thank you!” or, even better, stand there somewhat stunned and dazzled that such an incredible thing has just happened.

You have just become the kind and mysterious stranger who went out of his or her way to make someone else’s day a bit brighter.

How awesome is that?

The reason I generally recommend being an equal opportunity complimenter (age, gender, etc.) is because it helps demystify the act of talking to strangers as much as possible. This helps separate the fear of “approaching any member of the human race” from a more specific concern like “asking for that cute person’s phone number” (stay tuned for future articles, hint hint).

For what it’s worth, I have found that women above the age of fifty or so are particularly adept at receiving compliments from all walks of life, so feel free to start with them. Just beware—you may get your cheeks pinched. 

Once you see how positive of a response you can get from the average person on the street, you’ll start to neutralize the nervousness that comes from approaching strangers. Perhaps a person won’t let you vanish after you say your piece and will try to continue the conversation—which means they’re technically approaching you!

If you’re anything like me, you’ll be super nervous the first time you try this, but will be shooting off compliments like it’s your job within approximately fifteen seconds.

Two levels down, one to go!

Level 3: The Question Mark

Deep Conversation Question Mark

Now that you’ve mastered the art of blowing people’s minds with your spontaneous sprinklings of sweetness, it’s time to up the ante a little.

In Level 2, we proved that approaching people didn’t have to mean putting yourself out there or making a fool of yourself. But after all these compliments you’ve generously bestowed upon the world around you, you might be tired of not hearing anything in return. Enter The Question Mark, the perfect complement to a compliment:

  • Cool boots! Are they new?
  • What an awesome dog! What’s its name?
  • Those jeans are cool. Are they new? (Originality is overrated!)
  • Neat shirt! Where’s it from?
  • You’re so lovely! You having a good day?
  • I like your Trapper Keeper. Can I have it? Seriously, give it to me.*

 *This one is a joke. But if you try it and it works, please let me know immediately. Also, you’re my hero.

This perky punctuation mark is the linguistic equivalent of putting your hand out for a high five—you’re leaving a little something out there, and you hope that your partner doesn’t leave you hanging, but if they do, it’s not the end of the world. Frankly, if a person is too cool to tell you his or her dog’s name, the only appropriate response is to steal the pooch and run. And then you have a dog—win!

The Social Life Game!

Social Skills on Train

Alright, get to it! How many points can you rack up in a week? (Compliment = 1, Question Mark = 2)

  • 0-1 points (hopeless): Booger from Revenge of the Nerds – The girl from The Ring
  • 2-5 points (trying, but yikes): My name a Borat! – Allison from the Breakfast Club
  • 6-10 points (will talk to anybody):  George Costanza  – Leslie Knope
  • 11-15 points (social butterfly): The Fonz. EHH! – Princess Leia
  • 16+ points (always says the right thing): James Bond – Lara Croft

The great things about these exercises is they’re not just good practice—they’re also great opportunities for feedback and reflection.

  • What worked? What didn’t?
  • Was there a style that came more naturally to you? (Sweet, sarcastic, flirty, chummy?)
  • How does this match up against your goals from The Inception?
  • Were there certain people who responded better than others? How do you think the person you were thinking of in Level 1 would respond?

Overall, were you surprised by how positive the response was? Did it give you other ideas for ways to challenge yourself?

And finally, now that you have these beefed-up social skills, what else do you want to do with them?

I look forward to hearing your stories!

– Lindsay

Check out part 2, the 4 Step Plan to Not Suck at Talking to People.


PS – Check out Lindsay on Twitter @RellimYasdnil or send questions/comments at

photo source: coffee chat, train conversation, sitting chat, u rock, inception, feetlego men

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134 thoughts on “How to Be Awesome at Approaching People

  1. Hey, Appa! My compliments on getting so many compliments 🙂 Here’s a few suggestions for how to respond: “Why thank you!” “That’s a very nice thing to say.” “Thanks, it’s one of my favorite shirts (or books, or hats…).” That last one might be especially good for you because it turns the attention away from you-you-YOU and back toward whatever the person was complimenting.

    If a person has just approached you and said something nice, any of these responses will be enough to leave the door open for them to continue the conversation, if that’s what they’re looking to do, so don’t worry about figuring out what to say to push it along yourself.

    If, on the other hand, you’d rather not encourage further conversation (either because you’re feeling a little uncomfortable or because you’re simply enjoying your chai latte in peace), you could just smile slightly and give an appreciative nod, or say in a polite, measured tone, “Thanks, have a nice day.” You shouldn’t allow someone to make you feel icky, but it’s always good to keep in mind that they’ve done a scary thing by approaching you, and try to curtail the conversation without making THEM feel icky.

    Hopefully that’s sufficient, but if need be you could also say something like: “I should get back to my work now, nice chatting with you.” or “Alright, back to my book! Have a nice day.”

  2. I am probably dating myself a bit here but Trapper Keepers were thick binders with a velcro flap that you kept all of your school accessories in. Notebooks, pencils, pens, markers, etc. It was also a status symbol. God I am getting old.

  3. “[I’ve got class x now/this is my floor], maybe i’ll speak to you later, what’s your name?”

    And if it’s a prospective interest, you can stalk them later..  By which I mean you either email them or f/book or something.  Within a day (or even a couple of hours), just to say hi with a “it’s Andrew from the lift”

    Treat every instance as a practice for the next one, and don’t be put off by the one’s who don’t respond.

  4.  Yes I agree its to hard to keep bring our personal relation this busy era, but to me we should steal 1 hour or few minutes to discuss our issues, problems or achievements with our social life people. It will not only help us.

    I’m a Personal trainer in Gaithersburg

  5. Tried and true, 100% genuine technique – just find something you have situationally in common. If you’re both in an enjoyable situation, like at a party or a sporting event just say “great party/game huh?” If you’re in a not-so-enjoyable situation like waiting in line or stuck in an elevator say something like “I’ve waited my whole life just for this, haven’t you?” With a little grin. People love to feel included. So when you commiserate with them, or share in a pleasant experience, it will open up an opportunity to further dialogue. Or if they don’t want to dialogue, they can just say something non-commital like “yea” “sure” or “you’re weird.” 

  6. Excellent article!  I’ve been going to the same gym for four years and have only started talking to people within the last 7-8 months or so.  I see the same people all of the time because I’m at the gym all of the time but unless someone’s extroverted and approaches me, I won’t initiate conversation.  This is mainly because I don’t know how to!  These are some easy to use, hard to go wrong techniques.  Thanks!  This will add to my gym life 🙂

  7.  Sorry, but your examples are creepy.  No woman likes to be told “you’re cute when you’re angry” or “come sit beside me, yes, yes”  Ugh.
    It sounds like Nice Guy Syndrome.

  8.  lol, ok maybe not the best exsamples although i’ve used something similar after we been talking and they dont see me as a creep. LOL, to the nice guy syndrome, ive been called perv, stupid as they come closer etc. I will not go into detail’s since you might not be interested in it.

    Of course im not perfect

  9. Drive-by complements are one of my favourite things in the world.  Not only are they fun to give (get creative: check out mittens!  People love their mittens, and will talk about them for hours!), but when someone gives you a complement you don’t see coming, it really makes your day!

  10. Or even say something funny like “Man this line in taking forever” then ask the lady/guy in front or behind you the time “2:24”. “What! It it was 2:24 two hours ago” this line will give anyone a giggle and everyone knows laughter is the best ice breaker. 

  11. Hey Aaron!

    Thanks for the comment.  I’m afraid NF will keep disappointing you as I plan on continuing to cover various topics that help people level up their lives, not just fitness/diet articles. Thanks for reading up to this point, but it sounds like this might not be the community for you. 
    Best of luck to you bro. Cheers!


  12. Yes. Yes. Yes. This is exactly what this site’s been waiting for. Lindsay, you’re a goddess. Looking forward to more!

  13. Very well, Steve.

    I arrived to this site looking for tips on exercise and diet but I really like those articles on social life.

    It has great tips even for guys like me that are not shy to the extreme but that said  the worng thing at the wrong time in the past, didn’t like the experience and want ways to improve.

    Thanks a lot, Steve and keep up the good work!


  14. Great article! Keep it up. 

    Reminds me of a quote by Walt Whitman … 

    “Stranger, if you passing me and desire to speak with me, why should you not speak to me? And why should I not speak to you?” 

  15. Well met and well written with the best of intentions I’m sure, but careful when asking questions as some can come off as quite intrusive. For instance, whenever any stranger asks me where I got anything that they’ve just complimented me on, it never fails to annoy and put me on the spot as if they’re sizing me up. What business is it of yours where I got my expensive looking gadget/ fashion/ accessory/ power-up? When coming from the same sex it reads as competitive, whereas from the opposite sex it sounds opportunistic. And also, it’s best to voice appreciation for a feature/thing that isn’t so obviously or commonly esteemed. As an example, I have naturally awesome hair and am well aware of it. Whenever someone randomly comments on something that’s so effortless to me, which happens often, I’m like meh thanks but so what…you’ve completely missed the things that I’ve poured out my blood, sweat, and tears for. The main point, however, is to keep in mind that whatever praise that is delivered must be genuine otherwise it is flattery which is cheap and even trashy especially when it’s apparent that yer trying to talk me up to boost your own self esteem…don’t think that can’t be spotted from a mile away as, after all, I too am a nerd.

  16. Just because the URL is NerdFitness doesn’t mean this is JUST a workout site. It’s a self-improvement website–you can’t just change your body and magically fix everything. Articles like this are a great addition to becoming the person you’d really like to be.

  17. Just because the URL is NerdFitness doesn’t mean this is JUST a workout site. It’s a self-improvement website–you can’t just change your body and magically fix everything. Articles like this are a great addition to becoming the person you’d really like to be.

  18. My friends make fun of me because I’ve been using variations of the Drive-By Compliment for a few years, but I always pick things people aren’t used to being complimented on. Apparently “You have the most adorable nose!” makes it awkward to be seen with me in public. <.<

  19. They were pretty much the must-have school accessory of my youth, and still practically one of the coolest things on the planet.

  20. Instructions unclear: Complimented cute girl on her dog, got slapped by her ugly friend. She didn’t have a dog.

  21. I learned a lesson along time ago working retail. I found myself getting overwhelmed with crabby customers and whatnot, and it really effected my own mental state and made me bitter and awful, I was only seeing the worst in people and giving them my worst self. So, I decided to change my perspective by finding one nice thing aboit absolutely everyone I encountered, no matter what, and telling them when possible. That one small act has changed my life! Its become second nature to me to see the good!

  22. Few days ago I complimented a complete stranger’s moustache, straight out of the blue. Compliment + comic relief. Win!

  23. No, because, “Many of we nerds” isnt’ grammatically correct. 😉

    -A Grammar Nerd

  24. Recently I was extremely low on cash and debts were eating me from all sides! That was UNTIL I decided to make money.. on the internet. I went to surveymoneymaker dot net, and started filling in surveys for cash, and surely I’ve been far more able to pay my bills! I’m so glad, I did this.. With all the financial stress these years, I really hope all of you will give it a chance. – a6nc

  25. u8gy – Recently I would be so down on money and debits were killing me from everywhere!! That was UNTIL I found out how to earn money on the INTERNET! I visited surveymoneymaker p net, and started doing surveys for straight cash, and yes! i have been greatly more able to pay my bills! i am so glad, i did this!! With all the financial stress these years, I really hope all of you will give it a chance. B2P

  26. I have twin sons aged 12, one with aspergers and social skill problems. I think I”m actually going to let both of them read this, they are heading into Awkward Teen Phase and this is really good advice. 🙂

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