14 Fun Conversation Starters for Introverts Dating Introverts

The best conversation starters for introverts

You will not be surprised to hear that introverts and extroverts have vastly different feelings toward small talking. 

Extrovert couples rarely struggle with a limited social bandwidth. In an introvert-extrovert relationship, the extrovert usually shoulders the conversation in the early stages.

What about introverts dating introverts, though? How are introverted couples supposed to feel comfortable starting conversations and spending time talking with each other?

Small talk serves an important purpose. Consider how small talk can help two conversational partners “warm up” to each other by providing a gateway to more meaningful discussions!

Most small talk conversations tend to get stuck in a predictable rut before shifting to that satisfying deeper level. For introverts who value a few close, meaningful relationships more than a parade of surface-level ones, seemingly shallow interactions can sometimes feel a bit draining.

Today, we’re going to cover 14 fun conversation starters that can catapult small talk into much deeper territory!


Forced persona vs. personal growth

Introverts aren’t wired to thrive in shallow environments! As an introvert yourself, you likely get energized by playing with ideas, analyzing information, expanding your knowledge, and connecting authentically with others.

None of that happens when you make small talk… or does it?

While we totally understand how you might want to avoid small talk, you’ll want to consider if you are missing deeper opportunities to connect that are actually disguised in small talk.

Real confidence is the first step to recognizing potential in a seemingly shallow conversation and guiding the interaction gently into deeper territory.

Do you have that kind of confidence? 

Hint: Genuine confidence is rooted in knowing what’s uniquely magnetic about you.

You don’t have to pretend to be an extrovert or fake enjoying conversations that frankly aren’t your cup of tea. Personal growth for introverts in the context of small talk is simply the willingness to engage for the sake of a better conversation that could unfold.

When you know what draws people to you, you can find a path forward into more riveting conversations, whether you’re speaking with an introvert, extrovert, or someone you can’t quite figure out yet!

That’s exactly what this free 22-page ebook helps you with!

Download “Why PUA Doesn’t Work For Introverts & What Works Instead” now so you can circle back after you read this post!

Now, let’s dive in with topics you can use to liven up conversations with curiosity and interest! 


14 topics for introverts dating introverts

1. Your biggest dreams in life

What aspirations are you working towards? What are your goals and plans? Who inspires or motivates you, and what brings you back to life?

These types of questions literally cannot be answered with “small talk,” making them a wonderful path to deeper connections!

2. “Why” questions

Whether you’re speculating about the motivations behind human actions, personal struggles, or cultural triumphs, questions that get to the “why” of events, public or private, big or small, draw conversations into more engaging territory quite nicely.


3. What moves you and keeps you going

Whether you’re inspired by a family member’s good deed or an encouraging TikTok video, you can expect to feel moved yourself after hearing a response to this topic!


4. What’s really going on in your life

The human experience itself holds so much depth!

Whether this topic evolves into a conversation around sorrows and strife or celebrations and love, the possibilities are endless.

5. The big stuff

Maybe you’re interested in the nature of reality or the origin of life. Perhaps you’d rather talk about who we are and why we’re here, social constructs, or anything else that piques your interest!


6. What you’re struggling with right now

If you can create an environment where someone feels comfortable sharing about any problems or challenges they’re facing, you can maybe even then help brainstorm some solutions to alleviate some of the struggle!


7. Life lessons you’ve learned along the way

These types of conversations are often equal parts honesty and humor. Being able to laugh together about situations we wish we’d handled differently is a way to bond very quickly!


8. Your creative endeavors or hobbies you could get lost in for hours

Creativity comes in as many shapes and sizes as people do

Whether in the form of actual art like painting or sculpting, or a more general take on creativity such as collecting sea shells or hiking through dense forests, you’re sure to come away with an appreciation of what makes a person unique.


9. What keeps you up at night

Whether that’s a person’s hopes, fears, and goals or their literal dreams, this question can get a conversation to a very vulnerable place, which is a wonderful way to connect on a deeper level!


10. The parts of you that many people don’t know

The complexity of life experiences isn’t always honored in the fast pace of the everyday. You could work next to someone for decades and never know some of the stories they’ve lived through!

The best part about hidden gems in people is that they usually have to consider their thoughts for a moment before answering. This is because they have to choose a fact to share and then also choose how they want to share that fact with you!


11. How your values and ideas are evolving

This may come down to a conversation about personal growth or something broader like political views. Either way, these talks are fun because you get to see how people are changing, and how they feel about those changes.


12. An event that changed your life

Sometimes, people experience a pivotal moment that can alter the trajectory of their whole life. Wouldn’t you rather talk about that than the weather?!


13. Books

Many people can go on and on about the books they love: what they’ve read, what their favorites are, the ones they felt had a lot left to be desired.

You can easily start this conversation by asking, “Have you read any good books lately?” or, “I’m looking for some book recommendations. What’s your favorite?”


14. The topics that are usually absent from party chit-chat

Many topics can sometimes feel borderline taboo depending on how you approach them, such as religion, economics, politics, the stock market, cultural development, wars, history, the big picture, logic, and so on. 

Pro Tip: The name of this blog post is “14 Fun Conversations Starters” and to keep these topics FUN, you have to engage with warmth and openness rather than a desire to one-up someone or prove them wrong!


A few final thoughts for introverts dating introverts

introverts dating introvertsNow that you have an extensive list of topics to choose from, you’ll be able to choose which conversation starters for introverts dating introverts appeal to you most! 


Your Next Steps

Here’s what to do next to make sure your dating and leadership skills keep improving:

  1. For more conversation advice for introverts, read this article: Conversation Topics + Tips: Guide For Introverted Men.
  2. Download our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead” to build these dating skills on a foundation of confidence!
  3. For more personalized support, consider our Become A Benevolent Badass program.

Becoming more empathetic, authentic, humble, and confident doesn’t mean changing who you are. Developing your own unique vibe simply means becoming the best and truest version of yourself.

To powerfully accomplish that, consider Become A Benevolent Badass. Through our in-depth, personalized 1:1 coaching program, you will…

  • Find your inner true north and deepest sense of self,
  • Become your relaxed and playful best around others, and
  • Rise up as an intentional social leader.

Discover the best roadmap to enjoy better self esteem, foster deeper connections, and build a clear vision of what you’re creating today.

Picture of Micayla from IA
Micayla from IA
Micayla 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

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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

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