why dating is so hard

If you’re an introverted woman like me, and you find dating excruciating, you’re not alone. I receive countless emails and comments from introverted women who share the same frustrating challenges when it comes to dating and attraction. You’ll probably be nodding in agreement with these common struggles.

After all, you’re not like other women. You’ve probably grown up feeling different because of your quiet, sensitive nature. On top of this, you might have painful memories of your first interactions with men.

In my Amazon bestselling book, The Irresistible Introvert, I share the memory of my first crush. I was in kindergarten, and I had it bad for a boy named Kyle. One day, I got up the courage to sit beside Kyle during circle time. What happened next would shape my ‘dating story’ for the next two decades.

Immediately after I sat beside him, Kyle got up and walked to the other side of the circle to sit with his friend. It was my first experience with rejection. It wouldn’t be the last.

The dating and love story I told myself again and again was that I was undesirable and men would reject me. I had plenty of experiences in high school and my early twenties to reinforce this limiting belief:

  • Most of my high school crushes were oblivious to my existence, as they swooned for more popular, outgoing girls.
  • In my early twenties, I had a boyfriend who flirted with his charming and bubbly ex-girlfriend right in front of me on a regular basis.
  • Another boyfriend who had a strong extroverted personality tried to bully me into opening up, which only made me retract more.
  • Countless men used to call me out for my quietness, saying things like, “why are you so serious, smile!” and “You’re so quiet, say something!”

Again, if you can relate to the above experiences, I assure you that you are not the only one. But that doesn’t make it hurt any less. The dating struggles introverted women face can cause a lot of emotional pain. Not only that.

It makes your self-esteem plummet, which creates a self-fulfilling prophecy of rejection. Many innie women start to give up hope, choosing to avoid the heartbreak of dating altogether. You pretend you don’t care about finding Mr. Right, even though deep down you know that true love is all you’ve ever wanted.

Believe me when I say that I understand your pain and frustration, darling. And I’m here to tell you that there is hope.

Here are the top reasons why dating is so hard for introverted women, plus how to make it easier.

Energy challenges

Just like any form of socializing, dating is draining for introverted women. As someone who probably already struggles with low or inconsistent energy levels, going on dates only adds to the problem. But it doesn’t have to.

Here are 3 quick tips to manage your energy levels when dating:

 Keep dates short and sweet—especially during the initial stages. Don’t agree to go on a three-hour hike for a first date. Do say yes to a short waterfront walk that you can easily escape from at any point.

Come to dates with a full energy tank. Meditate or take a bath beforehand. You might also put on some calming music and take your time getting ready. This will recharge your energy tanks, plus give you a more relaxed vibe during the date.

Let go. Putting lots of pressure on yourself to look, act, walk, and talk perfectly on a date will only deplete you more. Let go of trying to steer the date by planning every step. Instead, think of yourself as a passenger on an exciting journey. Your main job is to be present and notice how you feel.

High expectations

Introverted women tend to have high expectations for both ourselves and the people we date. This can create a lot of anxiety and stress. Not only that.

It can also sabotage your dating life. To understand what I mean, consider this scenario:

Have you ever found yourself daydreaming about your future with a man that you haven’t even met yet? You connected online and he ticked off every box in the looks, height, career, and hobbies departments, so you decided he was THE man for you. There are a couple of big problems with this.

Men can FEEL your expectations. To him it feels like heaviness, pressure, restriction. And so he pulls away. Having high expectations also makes you more nervous and self-conscious. That’s why it’s far better to do your very best (and I know it’s hard, love) to stop putting men on a pedestal made of fantasies.

Fill your mind with other things, like creative projects, mindfulness, and self-loving thoughts. Seeing dating as an exploration or experiment will also help take the pressure off.


I’ve said it before and I’ll say it again: introverts have beautiful minds. Introverted women, especially, tend to be highly thoughtful and reflective. Unfortunately, your mind can turn into a destructive Tasmanian devil pretty quickly.

When dating, you get sucked into your own world of analyzing and worry. You overthink what you say and don’t say. Or pick apart a man’s every action.

Knowing how to master your mind when dating is a real game changer. It transforms everything from your body language, to your facial expressions, to your overall vibe. You’ll also feel more free to be yourself and actually enjoy the experience.

Feeling inhibited

For many introverted women going on a date with someone you don’t know can feel like trying to speak underwater. You feel disconnected and inhibited. The words you form in your mind don’t flow out properly. It’s not your fault.

Introverts have longer neural pathways for processing information. You need more time to take in what others say, and then formulate your own response.

My First Date Checklist gives you tools to feel more relaxed and open on dates, even if you normally feel like you’re in a straightjacket. Go here to download the Checklist—it’s free.

You’ll also receive articles on how to flirt without words, the art of poetic communication that mesmerizes a man, and other exclusive dating content I don’t share on the blog.


As an introverted woman, you likely spend a lot of time judging yourself. This self-judgment might also leak into your dating life.

You go into every dating experience with your gavel in hand, ready to judge everything from what a man says, does, and wears, to the minutest details of the date itself: “He didn’t compliment me in the first ten minutes of meeting—this isn’t going to work!”

One of my very wise mentors Elizabeth Purvis says, “judgment is the energy of punishment”. Ooooh, doesn’t that just get under your skin?

All the judging creates a vibe of punishment on a date. Neither you nor your date deserves to feel like you’re about to be sent to the naughty corner.

Thankfully, you can instantly turn things around by letting go of judgement in ALL situations. Gabrielle Bernstein’s book The Judgment Detox, will help.

I share all of this not so that you get more down on yourself, but so that you recognize this:

Your current dating story does not have to define the next chapters. You can have men crossing the circle for YOU. Best of all, you do not have to change your personality to attract good men.

Start with a few simple tools to change your mindset and vibe, and notice how men start reacting to you differently.

You deserve to be adored, my dear!



Michaela Chung