Overcoming shyness can sound pretty straightforward to many. They believe that you just have to learn a few tricks, and it will change your life. As a shy person in recovery, let me tell you, it is not a revelation. It’s an uphill battle against yourself. 

Shyness takes many forms, and some shy people out there are merely extroverts with a quiet streak. But for many of us, it’s an extension of introversion or social anxiety. Whatever your particular circumstances, it can be a bummer when trying to chat someone up. That’s why we’re going to help you learn to be less shy and more social.

1. You’ve Gotta Move Past Doubt

Dealing with loneliness is challenging and all-encompassing. It makes other problems feel worse and warps your thoughts over time. For an extrovert, this is especially crushing, but it doesn’t mean the situation is much easier on the introverted or socially awkward. 

The result tends to be a downward spiral of negativity, insecurity, and self-criticism. Without people to confide in, boost us up, or downright call us out, we get stuck believing our distorted thoughts are a reality, and that can cause further alienation. 

What does that look like? Maybe you’ve faced rejection or a setback and thought, nobody gets me. I’m terrible at this. These people aren’t worth anything to me anyway. This can cause you to stop trying or lash out. 

Well, slow your roll there! Everyone gets caught looking silly or being mistaken from time to time, and no one always gets what they want. But your thoughts have tricked you into thinking this is something abnormal and isolating. 

Devaluing yourself isn’t productive or useful, and these thoughts often find ways to slip into conversation. That creates even more awkward circumstances, almost like a self-fulfilling prophecy. 

The hardest part of how to be more social and how to not be awkward doesn’t involve anyone except yourself. Examine and try to alter your thoughts, feelings, and behaviors. Honestly, think through what you’d like to accomplish, and what’s holding you back. 

Then begin to relearn the power of vulnerability and the strength of resilience. Practice kindness and forgiveness with yourself. Acknowledge the worst parts of yourself (sans too much judgment) and find ways to work towards meaningful and lasting change. 

That’s admittedly a lot of work to try just to be good with the ladies! But it will improve everything from your mood to your confidence. Not only will you be able to talk to girls, but girls will also want to talk to you, and you’ll be prepared to approach those relationships. 

2. How to Stop Being Shy? Practice

So, of course, we totally stand by step one for everybody. We could all be more reflective and emotionally aware. 

But yeah, it doesn’t really explain how to overcome shyness. And what if your “Why am I so awkward?” isn’t tied to self-esteem issues at all? You love yourself, but the talking skills just aren’t there.

We develop and refine skills by doing them over and over. If something isn’t working, we have to adjust our methods. The same goes for chatting someone up. 

  • Let yourself smile at strangers who meet your eye. 
  • Engage in small talk with the people in your day until it becomes easier. Take note of what interactions go well and what they entailed, and which went poorly and for what reasons. 
  • If people don’t respond well to your advances, consider what the problem could be and tone it down, or completely correct course. If you can manage it, sometimes you might want to ask outright, hey, could you tell me what went wrong? I thought this was going well. 
  • If someone approaches you and typically you would shut them down, then next time, don’t. Instead, ask them how they are, ask them for help, crack a joke if you can think of one on the fly. 

It will often feel uncomfortable, and you’ll have to force yourself to do it. Your social awkwardness will feel front and center, but pushing through is a must. 

Warning: Do not push a conversation past its natural limit (being overly friendly with someone in customer service, for example, is less rude but as awkward as giving them the cold shoulder). Just realize that social opportunities are waiting everywhere. Take advantage of them while stakes are lower, and you’ll be ready when you want the conversation to really count. 

3. Give Yourself a Head Start by Planning Openers and Segues

Give Yourself a Head Start by Planning Openers and Segues

Quiet, shy people sometimes say they loathe small talk. It doesn’t lead anywhere, so it’s useless to engage in. If you consider yourself awkward, this is just another chance to say the wrong thing and mess the experience up before it’s begun. 

Both of these problems can be solved by planning how to deal with it ahead of time. Don’t let other people make all the rules. You’re an active participant, too, so act like it. 

  • How to become more social when you’re naturally recalcitrant? Find the path that takes you from something like, “What do you do/study?” to whatever you’re actually interested in.
  • Maybe it’s, “What did you want to do in elementary school?” or “What do you listen to while you commute?”
  • Such questions are contextually related but a little more fun and begin to open up the conversation and reveal more intimate details about the person. It might take a couple of questions to get here rather than just the one leap, but you can usually maneuver the conversation as desired.
  • How to be less socially awkward before you’ve found some kind of groove? You’ve just got to care about what the other person is saying, or at least proceed as if you do.
  • Your opener can be as simple as, “How’s your night going?” or “Is this your favorite drink?” or “What are you working on?” Rather than letting the conversation end, be interested. Share a tidbit in return and have a follow-up question. People will notice the effort and appreciate genuine curiosity. Give them a chance to do the talking for you.
  • But people also tend to answer small talk with small answers, so having generic follow-ups like, “What’s the best thing that’s happened to you today?” or “Do you think I should get this then?” or “That sounds hard, do you enjoy it?” is useful.

Warning: if she continues being curt or doesn’t engage with eye contact or other good signs (think smiling, emojis, longer answers), she doesn’t want to have a small or big talk. Take the hint, say thanks, good luck, goodbye, and move on. You two don’t currently have a middle ground to stand on, and there’s no need to exhaust her and yourself trying to find it. 

4. Put Yourself Out There

There’s no way around it: you can’t meet people and talk to people if you don’t go where they are.

This doesn’t necessarily mean you have to suffer through a party atmosphere you hate. Accept an invitation if you suspect you could have a good time, but also branch out in ways already compatible with your tastes. Communities can be physical or virtual as well, so don’t ever act like reaching out online doesn’t count. The effort is real!

In any case, the focus shouldn’t be learning how to not be shy. It should be finding ways to enjoy your time and the company of others. In situations of your choosing, the conversation will be easier anyway, because you’ll be interested, invested, or knowledgeable in the experience, as will the people around you.

5. Introduce Yourself

Introducing Yourself Unprompted

Talking to girls — and talking to anyone, but girls, especially for some reason, is intimidating. You have to be bold. Not so bold as to be rude or inappropriate, but in ways that may feel a bit strange. 

One of those strange ways is introducing yourself unprompted. Attaching your face to a name is crucial (even if she soon forgets what that name is through no fault of your own) and encourages reciprocation. Using names is a proven way to hold someone’s attention. 

And if you have a few pre-thought outlines to introduce yourself beyond the name, you’ll be more memorable than not. “I’m Evan, I worked with the nuclear power on a Navy sub.” is perhaps a winning example, but unless you’re Evan and worked with nuclear power on a Navy sub, you’ll have to come up with your own winner. 

Finally, it means fewer missed connections. People can ask about or try to find you again if they’re interested. If you’re feeling extra confident, you can go from exchanging names to exchanging numbers or even dinner plans. It’s worth a try, at least while you’re in the moment.


There’s no magic trick for how to not be socially awkward, or not think that you are. It takes work and believing in yourself, and some faking it until you make it. How to stop being awkward involves no quick, easy steps for those of us who are indeed awkward, shy, or anxious. 

But if you prepare then practice then reflect, you can make things easier almost every day. Take the smallest of baby steps if you need to. Be gentle but honest with yourself when you truly mess up or take a step back. Otherwise, don’t be overly critical and recognize your successes. 

More than anything, see if you can make these changes for yourself before you start making them just for romance.