Striking Up a Conversation: 5 Hacks for the Introvert

“I want to talk to a woman, but I don’t know how to start the conversation.”

She sits right across from you at work, but she might as well be a stranger.

She smiles at you several times in the deli aisle at the store, but neither of you make a move.

Or she takes your coffee order every morning, but that’s the extent of the things you’ve said to each other.

Every time it happens, you want to say something. But you hesitate.

Sound familiar?

Today’s post is about taking that first step and striking up a conversation with a woman you really want to talk to.

We’ll cover these five helpful tips:

  • Asking yourself, “So what?”,
  • Using questions to break the ice,
  • Sharing a detail about yourself,
  • Recognizing when to move on, and
  • Knowing when it’s going well.

Ready to jump in?

First, let’s talk about seizing opportunities.


Why is it important to be comfortable with striking up a conversation?

Life is a choose-your-own-ending story.

You don’t realize before you make a decision what impact that decision will have on the rest of your life. The impact is even greater when it’s a whole pattern, a mosaic of decisions that spans years or decades.

If you’re the type that always chooses “Flip to page 107 if you want to take the safe road,” you may often find yourself surprised that the safe road wasn’t really all that safe at all.

Sure, by not opening yourself up and talking to women you’d really like to say hi to, you’re less likely to feel awkwardness, rejection, or any of those other negative feelings you’d rather avoid.

But how about the feelings of missing out, of wondering what could have been, or of letting life happen to you instead of taking charge?

Taking charge of your social life will probably feel uncomfortable from time to time. But the rewards far, far outweigh the risks.

After all, what’s a little awkwardness in comparison to a lifetime of growing, learning, and hopefully finding your soulmate?

Do you ever wish you could flip a switch and suddenly understand the things about yourself that you like and the things you want to change? Download this free ebook and use the exercises to do exactly that. Then, build a plan to maximize your awesomeness using that knowledge! >> Improve your confidence here. <<

Now let’s get started on initiating some conversations using these tips:


1. Ask yourself: “So what?”

Plenty of introverts don’t start conversations because they simply don’t feel like talking right then. And that’s okay!

However, you’re reading a post about purposefully striking up conversations, which means it’s something you want to do at least sometimes.

Starting a conversation is technically as simple as saying “hello” to someone and asking about the weather; it isn’t a complex process. Which means that something is holding you back.

That “something” is likely anxiety.

You see a nice-looking woman and your mind starts going a mile a minute:

“What do I say to her?”

“Will she think I’m being creepy?”

“What if I feel uncomfortable and want to leave? How do I end the conversation?”

What do all of these worries have in common? They stem from the thought that the other person might have a negative thought about you or that the interaction might feel awkward.

And to that we say…

So what?

If the conversation goes well, you might walk away with her phone number and a smile on your face.

If it doesn’t go well, you haven’t lost anything at all, and in fact have gained valuable experience by striking up a conversation with a stranger. That minorly awkward interaction just gave you a lot more practice at stepping outside of your comfort zone and raising your threshold for social discomfort.

Either way, that’s a win.


2. Ask questions you actually want to hear the answers to.

Asking a question is one of the most accessible ways to begin a conversation with someone you don’t know. That’s why we used the example of asking about the weather in the previous section.

However, there is a catch.

If there’s one thing most introverts are likely to agree on, it’s that small talk is pretty much the worst thing ever invented.

Though starting a conversation is as simple as asking someone about the weather, it’s not exactly a topic that speaks to your soul, is it?

As an introvert, it’s your natural tendency to avoid all things shallow and inconsequential. So, work with your strengths.

Depending on the context of your situation, you could try asking something like…

  • “What do you think of this seminar? Learning anything valuable?”
  • “How are you doing with your new job here?” (And then genuinely care and show interest in her answer!)
  • “Is it just me, or was that movie entirely missing the point?”

The key is to aim for topics that prompt her to share her own opinions and ideas. For some good ideas, check out this article.

That will build that intimate feeling of truly getting to know one another much more quickly than small talk ever could.


3. Volunteer some information.

We don’t mean that you should walk up to a woman and blurt out, “As a kid, I loved dinosaurs.”

Well, you could, but unless she’s a paleontologist that strategy probably won’t be a winner.

The key here is to share something relevant to the situation, interesting, and just a little bit deeper than surface-level.

Ideally, you can also use this opportunity to draw a parallel between the two of you.

Need some ideas?

Again, depending on context, share something along these lines:

  • “I used to have that exact car! It’s a funny coincidence because I rarely see them in that color.”
  • “Oh, nice band t-shirt. That’s my favorite group.”
  • “I see your dog is having some trouble with pulling on his leash. I used to be a dog trainer, if you’d like a quick tip.”

You want to pique her interest and make her want to ask follow-up questions.


4. Pay attention to clues that she might not want to keep talking.

Some of the hesitation you may feel about striking up a conversation comes from not knowing ahead of time how someone will react if you try to speak with them.

The good news is that even if you start a conversation with a woman who isn’t in the mood to talk, you can skillfully recognize those hints and move along well before things get actually awkward.

Things like…

  • fidgeting
  • scanning the room with her eyes
  • turning her body away from you, or
  • using short, clipped answers

… are all indications that the conversation should wrap up soon.

Try not to take this personally!

(Again: “So what?”)

She might be in a hurry to get somewhere, tired after a long day, or a very shy person.

You can absolutely handle this gracefully and leave both of you feeling like it was overall a positive experience.


5. Read her cues that she is interested.

On the other hand, if she is…

  • paying rapt attention,
  • adding meaningful contributions to the conversation,
  • asking interested questions, and
  • making eye contact

… you can interpret that as her enjoying the conversation.

No need for gray areas and guessing!

You can use that as a basis for moving toward deeper topics, asking for her number, or even asking her out and then making your exit while things are obviously ending on a good note.


Conclusion on striking up a conversation:

Man and Woman Laughing - Striking Up a ConversationThough speaking to someone you aren’t familiar with might seem risky, it’s by far less risky than staying in a comfort bubble that never allows you to reach out and meet anyone new.

Hopefully today’s tips will resonate with you next time you find a lady you’d love to chat with.


  • Let the tiny risk of awkwardness roll off your back,
  • Ask questions you genuinely care about,
  • Share a piece of yourself,
  • Learn when to step back, and
  • Recognize when to keep going.

To make sure you’re operating at full confidence capacity before striking up a conversation with someone new, download our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead.”

Coming up against some very particular challenges? Not sure where to get advice that fits your situation? We’ve got you covered. Join our Launch Your Dating Life program for personalized, customized dating advice for your individual needs. You can apply here for a 1:1 phone call and together we’ll see if this program is a good fit for you.

Picture of Kelly from IA
Kelly from IA
Kelly is resident writer here at Introverted Alpha, which is known as the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of our 22-page ebook inside the blue box just below.

Attracting An Amazing Girlfriend Starts with Finding Your Own Vibe.

Introverted Alpha Ebook

In this powerful free 22-page ebook, “Why PUA Doesn’t Work for Introverts And What Works Instead,” you will uncover… 

–> 3-step exercise to find what makes you uniquely attractive

–> Why the “pickup artist” approach will never work for introverts and what works instead

–> How to attract women naturally being your best self

"I love how personalized and caring you guys are at Introverted Alpha! It's so wholesome and refreshing." - I.L.

"I especially like how you’re a strong alternative to short-term, shallow PUA tactics." - K.K.

Recent Articles

Leaving Already?

Before You Go...

Schedule a call with us to improve your dating life immediately.

Couple In Love - IA Academy - Introverted Alpha

Attracting An Amazing Girlfriend Starts With Finding Your Own Vibe.

In this powerful free 22-page ebook, "Why PUA Doesn't Work for Introverts And What Works Instead," you will uncover...


--> A 3-step exercise to find what makes you uniquely attractive
--> Why the “pickup artist” approach will never work for introverts and what works instead

--> How to attract women naturally being your best self

We respect your privacy; we do not sell or share your email address.

Introverted Alpha Ebook

Yes, please send my ebooks!

You can send them to...

Yes, please send my ebook!

You can send it to...

Scroll to Top