Advice for Shy Guys:
13 Things About Socializing I Wish Someone Had Told Me When I Was 21

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Advice for Shy GuysAs anyone who’s ever felt nervous before a party knows, socializing – meaning the act of meeting and talking to people (especially new people) – can be incredibly intimidating.

It took me the better part of a decade to figure it out, and even now I can’t claim to be an expert.

But I’ve certainly come a long way since my days as a timid and intimidated 21-year-old.

Unfortunately for my younger self, time travel continues to not be a real thing (thanks for nothing, Michael J. Fox), so I can’t go back to share my newfound wisdom with 21-year-old Dave.

But what I can do is provide advice for shy guys who want to get better at socializing today, rather than a decade from now.

Below you’ll find 13 lessons about interacting with other people that I wish someone had told me when I was younger.

Advice for Shy Guys

Making Socializing Easier:
13 Pieces of Advice for Shy Guys

1. Social Skills Can be Learned

Advice for Shy Guys
If only THIS class had existed…

I spent far too much time in university lamenting what I perceived to be my weaknesses: shyness, introversion and a lack of social skills.

I’d see naturally extroverted people easily bouncing around at bars and pubs, meeting new people and saying hi to their many friends, and feel overwhelmed with feelings of envy and shame that I just “wasn’t like that.”

Years later, I must have looked like a cartoon character when I read Dale Carnegie’s How to Win Friends & Influence People for the first time – I could practically feel the light bulb springing to life above my head and illuminating me.

Among the many things that book illuminated for me, the most fundamental was this: people skills are just that – skills. You can actually learn how to do things like start conversations, make other people feel good (about themselves, and you) and want to be your friend.

This knowledge alone was a revelation to me, and the ensuing tips and tricks I learned from Carnegie’s book – and others like it, including Leil Lowndes’ How to Talk to Anyone & How to Instantly Connect with Anyone, Susan RoAnne’s How to Work a Room and many more – made me realize that I didn’t need to be some gregarious life of the party in order to be more social.

All I needed was a little education.

Socializing Tip #1:

Remember that social skills can be learned. Don’t kick yourself if you don’t have them – just set about trying to learn them. Check out this blog post about becoming more social for a good place to start.
Advice for Shy Guys

2. Other People Are Shy, Too

Advice for Shy GuysPart of the reason I found talking to other people so intimidating in my early 20s is because I erroneously assumed that I was a below-average socializer.

For some reason, I had this idea in my head that most people were at least average – meaning that as someone below average, I was at a disadvantage with the majority of people I came into contact with.

But the truth was that I was so nervous about talking to other people that I retreated into myself. As a result, I largely ignored the thoughts and feelings of others, which prevented me from seeing that most of them weren’t exactly social butterflies either.

I was so fixated on the (very) small number of people who actually are naturally social, I couldn’t see the hundreds of average, introverted and shy people lined up behind them.

Over time I realized that I actually had pretty average people skills, and many people who I came into contact with were either average, or even below average.

This realization immediately made talking to other people less intimidating.

Socializing Tip #2:

You’re not the only shy, introverted person – far from it.

Next time you’re in a situation where you have to choose between keeping to yourself or striking up a conversation with a stranger, try to remember that they probably want you to make the first move as much as you want them to.
Advice for Shy Guys

3. Introversion ≠ Shyness

Advice for Shy Guys
Shyness, represented on top, is a fear of judgment. Introversion, on the bottom, is a preference for quiet environments.

This is definitely something I didn’t know when I was 21. In fact, I didn’t actually learn it until I was 31!

It wasn’t until I read Susan Cain’s book Quiet that I realized just how different introversion and shyness are.

As Cain writes on her website, “Shyness and introversion are not the same thing. Shyness is the fear of negative judgment, and introversion is a preference for quiet, minimally stimulating environments.”

This alone was a revelation for me. For years I felt like some anti-social hermit because I got uncomfortable at big parties or in other stimulating social situations.

But I also felt confused, because I loved going to my favorite bars and hanging out with a group of friends, even when that group consisted of a lot of people.

My failure to understand how both those things could be true caused me a lot of cognitive dissonance and discomfort.

Learning that it’s perfectly possible to be introverted, if not exactly shy, alleviated a lot of anxiety for me.

Social Tip #3:

Don’t fret too much if you can’t understand why some social situations scare you and others don’t.

And don’t be too hard on yourself if you would genuinely prefer to stay in with a good book rather than go out to some rager.

You’re fine, you’re normal and you’re sure as hell not alone.

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4. Extroversion ≠ Superiority

Advice for Shy Guys
It’s tempting to think that because George Clooney charms his way through movies, you should charm your way through life. But don’t buy into the extrovert ideal.

The other great revelation that I got from Cain’s book Quiet was her notion of the Extrovert Ideal.

I wrote a whole post summarizing it, but basically Cain suggests that so much of Western culture is built around the notion that being extroverted, outgoing or gregariousness is superior.

This seems to go double for men, who, the cultural assumption goes, are supposed to be the more assertive gender.

We frequently watch movies and TV shows where the leading man has no problem talking to women or other strangers, taking charge of a situation and (more often than not) easily charming his way through life.

Naturally we’re left with the impression that this is how we should be, too.

But Cain’s book is essentially devoted to making the case that this isn’t true: introversion is not just “OK” – in its own way, it’s actually awesome.

There are a lot of benefits to being an introvert, including increased self-sufficiency, deeper relationships and a greater appreciation for subtlety and nuance, to name just a few.

Social Tip #4:

Don’t be taken in by the extrovert ideal. Pick up Susan Cain’s book Quiet: The Power of Introverts in a World that Can’t Stop Talking to read her full, compelling argument for the power of introverts.

Advice for Shy Guys

5. Don’t Rehearse Negative Scenarios That Will Never Happen

Here’s one of my favorite quotes, which is often attributed to Mark Twain.

“I am an old man and have known a great many troubles, most of which never happened.”

Regardless of where the quote originated, it gets at an essential truth that many of us can probably relate to: the tendency to imagine negative scenarios that will never come to pass.

Advice for Shy GuysThe Damaging Effects of the Dark Side

I’ve written before about how negative thoughts will of course come to mind – that’s totally natural, and not your fault. But spending too much time indulging in these negative fantasies is not just useless, it’s potentially damaging to your long-term mental and emotional health.

“The more you focus on negativity, the more synapses and neurons your brain will create that support your negative thought process,” write Susan Reynolds and Teresa Aubele in Psychology Today.

Think of your brain as a sort of sponge: it soaks up what you put into it.

Thinking positively will train your brain to be more positive. Likewise, thinking negatively will prime your brain for negativity, which among other things will slow your ability to process new information, limit your problem-solving capability and negatively impact your mood and impulse control, according to Reynolds and Aubele.

Socializing Tip #5:

Catch Yourself in the Act

When you catch yourself going negative, stop and take a deep breath. Recognize what you’re doing, remind yourself that while it’s not your fault, it’s also not helpful, then redirect your thoughts elsewhere.

Not only will you immediately feel better in that moment, but you’ll find you waste less and less time thinking negatively for no reason.

Advice for Shy Guys

6. Small Talk Isn’t Nearly as Banal as It Seems

Advice for Shy Guys
Or as we’d say here in Canada, “I know, eh?”

I used to get a lot of mileage out of telling myself “I just don’t like small talk.”

It was too banal, too shallow, too perfunctory. I was better than that, I thought. Deeper. More interested in philosophical discourse than everyday prattle.

But in my heart of hearts, I knew this was bullshit – a lie I told myself to shield my fragile ego from the truth. The real reason I disliked small talk wasn’t because it is was banal – it was because I was no good at it, and I was jealous of those who were.

The truth is that small talk isn’t petty – it’s vital. Think about it.

You’re not going to have a deep, intellectual conversation with someone who you just met. It can take time to develop that type of relationship.

And more often than not, you build up to that type of relationship by having a series of smaller, less intimate conversations.

Small talk is how we both start and build relationships. Sure, it might feel shallow or even disingenuous to talk about the weather, or the news, or the local sports team.

But these low-stakes conversations let you dip your toe into relationship waters and determine whether or not you want to dive in deeper.

Socializing Tip #6:

Don’t skip out on small talk because you think it’s beneath you. Instead, learn how to get good at it and marvel at the many new friendships it allows you to form.

Advice for Shy Guys

7. What You Say Doesn’t Matter (Much)

Advice for Shy Guys
“I have literally no idea what he’s talking about, but I like his smile.”

And while we’re on the topic of small talk, I’ve got more good news: the truth is, it doesn’t really matter what you talk about.

This was a tip I first got from the Leil Lowndes book I mentioned earlier, How to Talk to Anyone. I read it when I was about 26, but I wish I had learned this years earlier.

I would always spend so much time fretting about what exactly to say that I ignored an obvious truth: how you say something is just as important – in fact, maybe even more important – than what you say.

Think about the people you most enjoy talking to. Sure, the list may include people who have deep knowledge on a few of your most cherished topics. But I’d be willing to bet that those people only make up a small percentage of your list.

Chances are, the people you most enjoy talking to are the ones who have a friendly cadence and tone, who listen more than they speak and, when they do open their mouths, color almost everything they say with an optimistic, positive, fun or humorous tone.

Becoming aware of this was hugely liberating for me. It relieved me from feeling like I always had to say the “right” thing because it meant almost anything I said would be “right,” as long as I said it in an appropriate tone.

Socializing Tip #7:

Worry less about your words. Instead, focus on your tone. Speak in a positive and upbeat cadence, and people will appreciate (almost) anything you have to say.

Advice for Shy Guys

8. People Love to Talk About Themselves

Advice for Shy Guys
People appreciate when you give them a chance to talk about what’s going on in their lives. Whatever that might be…

Again I’ll quote from what I think is the seminal book about socializing, Dale Carnegie’s How to Win Friends & Influence People:

“Talk to someone about themselves and they’ll listen for hours,” he wrote.

This was as true when Carnegie wrote it in 1936 as it is today.

The beauty of Carnegie’s advice is how simple and self-evident it is.

Whether you know it or not, you love talking about yourself: your interests, your hobbies, your accomplishments – just about anything that pertains to you.

And you’re not alone. Everyone loves talking about themselves and the things that interest them. Give people a chance to do so and you’ll immediately win them over.

Real World Example:

I was at a party last year where a friend of a friend – someone I had never met before – mentioned he had just gotten back from a family vacation to Portugal.

That was all it took to spark a 20-minute conversation about Portugal, a place I’ve never been to and don’t have much interest in visiting. (Sorry, Portugal.)

So, how did I keep the conversation going so long? All I did was ask open-ended questions about the trip, a topic I could plainly see he was interested in.

“What was your favorite thing about Portugal? What was the most surprising? What’s the weather like there at that time of year? How was the food there? They make some wine there too don’t they?”

By giving him a chance to talk about himself, I not only got to know him better and establish a connection, I was able to leave him with a positive impression of me.

And I barely had to open my mouth.

Socializing Tip #8:

Ask people about themselves and their interests, and really listen as they answer.

Advice for Shy Guys

9. Smiles Are Everything

Advice for Shy GuysThis one may seem small, but you’d be shocked at how effective it is.

Smiling makes almost every social situation better.

Smiling Makes Other People Feel Good

Smiling can make you seem more approachable.

One study found that people are more willing to engage socially with others who are smiling.

And the benefits don’t end with increased approachability.

“A smile suggests that you’re personable, easy going, and empathetic,” she continues. “In fact, a study in the European Journal of Social Psychology found that smiling actually makes you more attractive to those you smile at.”

Smiling Makes You Feel Good, Too

Advice for Shy GuysAs if that weren’t enough reason to grin, smiling has been shown to have significant benefits to both your brain and your body.

Smiling helps you manage stress, relax your body and lower both your heart rate and blood pressure, according to Sarah Stevenson in Psychology Today.

“Each time you smile at a person, their brain coaxes them to return the favor,” says Stevenson.

“You are creating a symbiotic relationship that allows both of you to release feel good chemicals in your brain, activate reward centers, make you both more attractive and increase the chances of you both living longer, healthier lives.”

And here you thought smiles were just upside down frowns.

Socializing Tip #9:

Smile more. At first it may seem weird to make a conscious point of smiling, but do it anyway. You’ll instantly feel better about yourself, and make other people feel good, too.

Advice for Shy Guys

10. Inaction is Way Worse Than Awkwardness

Advice for Shy Guys
How guys afraid of taking action spend their Saturday nights

I didn’t date much in university.

Actually, I should clarify.

It would be more accurate to say I only went on a small number of dates in university.

Maybe I should clarify further.

It would be most accurate to say that I only went on the smallest number of dates possible in university.

Which is to say, the number of dates I went on is one. (Can you really say the number of “dates” when the answer is one? Grammar: almost as tough as dating.)

An Asshole Avoiding Awkwardness (Alliteratively)

It’s not that I didn’t have opportunities. Over the years there were plenty of girls I was interested in, and a few who even expressed some interest in me.

It’s just that I was terrified of going on a first date.

What the hell would I talk about? What’s the proper etiquette? Do I pick her up, or do we meet somewhere? Do I walk her home? Do I kiss her at the end? Will she even want me to kiss her at the end? How will I know?

I was so afraid of awkwardness that I never asked a single girl out. (On the one date I went on, the girl asked me out, in case you were wondering.)

So to avoid going on awkward dates, I went on no dates. Instead, I sat at home with my roommate, playing video games and pining over the social life I could have had, but didn’t.

Failing Upward
Advice for Shy Guys
My early dating experiences were… less than stellar, let’s say.

Fortunately, after university I moved to a big city. I didn’t have a roommate anymore, and after years of inaction I was finally so fed up with myself that I created a profile on a popular online dating site (alright, fine: multiple online dating sites) and started putting myself out there.

And, yep: shit got awkward.

In my earliest dips into the dating pool, I was not a good date. I struggled to come up with date ideas, didn’t know what to say and generally just stumbled through the whole thing. On more than one occasion I was so nervous beforehand that I almost cancelled before we met up.

But I didn’t. I resolved to keep going on first dates, awkward though they were, until they got easier.

And it worked… eventually.

Over time I got better, more comfortable, even confident on a date. It wasn’t easy – in fact, sometimes it wasn’t even all that fun.

But it was a hell of a lot better than staying home and playing video games on a Saturday night.

Socializing Tip #10:

Don’t avoid social situations because you’re afraid that they’ll be awkward. They will be awkward – at least at first.

But the only way to make them less awkward is to practice them.

Again and again and again.

Advice for Shy Guys

11. You Can Fake It ‘Til You Make It (Sort of)

Advice for Shy GuysI know, I know: this is one of those jargony self-help sayings that sounds a lot like bullshit – even when it’s coming from no less an authority than a Harvard professor.

But you don’t need a degree in psychology to know that it’s true. You just need to have experienced it for yourself.

My dating experience above is a great example. On those first few dates, I didn’t know what the hell I was doing, and it showed.

But over time I started to learn a little bit more about how to be a good date. It still totally terrified me, but at least I had some idea what I was doing.

This led me to feel like I could do it, which in turn made me less terrified.

And eventually I went from feeling like I could do it to knowing I could. After that, going on dates actually became fun.

Now, don’t get me wrong: I’m definitely not advocating that you pretend to be someone you’re not. (Read the next tip to find out why.)

But I am saying that if you follow the previous tip and take action – even action that puts you outside of your comfort zone – you’ll find that it gets easier each time.

And as a result, you get better and better at socializing – or anything else you’re trying to achieve.

Socializing Tip #11:

Fake it until you make it. Put yourself out there and resolve to keep doing so until you get better – at small talk, at dating, at going to parties, at whatever it is you want to achieve.

Advice for Shy Guys

12. It’s Easy to See Through Phoniness

Advice for Shy Guys
How I wanted to look at parties…

Remember earlier when I described the dread I used to feel when I went to parties?

What I didn’t tell you was how I acted after I finally mustered up the courage to go.

I played it totally cool. I did a super-sweet cool guy lean against whatever flat surface was available, looked brooding and mysterious while not saying much, and left everyone there with the impression that I was deep, soulful, enigmatic and alluring.

At least, that’s what I told myself.

In truth I probably looked more like this:

Advice for Shy Guys
How I actually looked at parties

After all, that’s kind of how I felt.

And as much as I would have loved to believe that I was hiding my wallflower feelings behind a finely tuned mask of mystery and bravado, the truth is that everyone could see right through it.

And if you’re doing something similar, they can see through you, too.

Instead of pretending I was totally cool, I would have been way better served if I admitted my awkwardness, even if I couldn’t quite bring myself to embrace it.

I know it’s tough – hell, it may even seem impossible – but ultimately, it’s better to be the guy who’s shy but earnest than the guy who’s shy and desperately trying to hide it.

Socializing Tip #12:

Don’t try to mask your shyness or introversion by acting brooding or mysterious. You won’t come off as cool, you’ll come off as insincere and insecure – which is exactly what you’re trying to avoid.

Advice for Shy Guys

13. Grow Your Social Circle to Grow Yourself

Advice for Shy GuysWhen I first went to university, I was so afraid to meet new people that I told myself yet another comforting (and bullshit-rich) lie:

“I have enough friends.”

Like most good lies, it had a hint of truth to it; I did indeed have a lot of great, close friends, for whom I felt really grateful.

But with the benefit of hindsight, it’s become obvious that I was just fixating on this truth as a way to avoid another, far less comforting one: that talking to people and making new friends intimidated the hell out of me.

Thankfully, I had no choice but to disavow myself of the whole “I have enough friends” lie.

Because, while I did have some great friends in high school, not a single one of them went to my university – which meant that my only two options were to make some new friends or prepare myself or an extremely lonely (to say nothing of boring) four years.

Advice for Shy GuysAnd thank god I did. By opening myself up to new people I expanded not only my social circle, but my horizons. I met people from all walks of life and corners of the globe who taught me about themselves, their passions and the worlds they came from.

My life is far richer, happier and more fulfilling because of these people. I hate to think where I’d be if I hadn’t forced myself to embrace them.

Socializing Tip #13:

Remain open to meeting new people and making new friends. Yes, it can sometimes be intimidating. But it’s also richly rewarding.

Don’t let your fear keep you from enjoying one of life’s great pleasures: developing real, lasting bonds with other people.

Advice for Shy GuysWant to Make
Great Small Talk?

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Photo Credits:
Tip #7 photo designed by Peoplecreations –
Smiling people on bench & in Tip #13 photos designed by Javi_indy –
Video game controller & awkward date images designed by
Silhouette of people jumping image designed by Kjpargeter –

About Dave Bowden

Dave Bowden

Irreverent Gent founder Dave Bowden is a style blogger whose advice on how to look good and live well has been featured in some of the world’s most trusted publications, including New York Magazine, The Wall Street Journal, Business Insider and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well. (Don't worry—it's less creepy than it sounds!)

8 thoughts on “Advice for Shy Guys: <br>13 Things About Socializing I Wish Someone Had Told Me When I Was 21”

    • You’re definitely not alone in that Stuart. I still sometimes catch myself falling into the trap. The important thing is just to recognize that’s what you’re doing and shut it down before you go too deep down the rabbit hole.

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