Can a Quiet, Quirky Woman Ever Find Love? + Workshop Announcement

Written By Caroline Smith

You want to be seen. But every time you think about starting a conversation, you freeze. You overthink what to say and how to act. You worry you’ll come off as awkward, thirsty, too much — or not enough.

You’re not alone and you’re not broken, although it may seem that way right now.

If you’re anything like I used to be, you’ve spent years watching other women date and get a man’s attention with no problem, wondering if you’d ever even figure out how to start.

You’ve got silent crushes, fantasy relationships you’ve dreamed up in your head, and a long list of reasons why you probably don’t stand a chance.

Well, I’ve got some good news: You DO stand a chance, and that’s exactly what my upcoming workshop, Dating With Confidence (For Quiet, Quirky Women) is going to help you understand!

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Transcript:

Hello to all of the introverted misfits who are tuning into this episode of the podcast!

I have a big announcement: I'm hosting my first virtual workshop, Dating With Confidence (For Quiet Quirky Women)! It’s going to be held August 22, 2025!

But first, I want to explain the inspiration behind a workshop of this nature by telling you my personal story of finding love as the introverted misfit / quiet, quirky woman that I am:

If you regularly listen to my podcast, it’s no secret that I am on the autism spectrum — diagnosed at 17 with what was then referred to as Asperger’s Syndrome — and I consequently struggled with some pretty bad social anxiety which is something that made finding love and dating an impossible feat for me.

In fact, at the time I’m sitting down to make this podcast episode, I have never been in an official relationship, and — brace yourself — I’ve never even had my first kiss with a man.

I know what you’re thinking — why on earth would I want to sign up for a workshop hosted by a woman who has so little experience?

And to that I say, just hear me out. Listen to what I have to say, because although I may be inexperienced in some of the heavier relationship areas that I’ve yet to encounter, I think you could learn a lot more than you think.

I didn't go on my first official date until I was 22.

I didn’t go to prom, or the homecoming dance, not even a movie date accompanied by parents. I was 22 — a super senior in college.

Quick side story, I did have the opportunity to go to prom during my junior and senior year of college, but both times I was asked, I had such low self-esteem that I thought those guys must be playing a prank on me or something, and I sort of rudely declined both offers.

I thought so poorly of myself that I couldn’t imagine anyone would actually be interested in me, but that’s something I’ll talk more about later in the episode.

Back to my first date at 22 — I completely bombed it.

I wore baggy sweatpants, an XXL sweatshirt, and a toboggan hat to cover up my undone hair. And naturally, I was very shy and awkward the entire time.

The worst part is he was actually a great guy: really quiet like me, kept to himself mostly, was a little shy but in a cute way, he was very tall, attractive, and had this beautiful dark brown skin tone.

I wish I could go back in time and explain to him that I was not in the right headspace to start dating, but the past is in the past and there’s nowhere to go but forward.

It wasn’t until 3 years later at the age of 25 when I went on my second date ever, which went much better than the first considering I had finally broken free from my social anxiety and decided to wear some better clothes.

I think we got 3 or 4 dates/hangouts in before it kind of fizzled out.

But unfortunately, it wasn't all smooth sailing.

As all inexperienced women have to learn someday, the world of dating and finding love is scary when you don't know the rules.

I found that out the hard way when I broke my own heart by developing a major, silent crush on a man I only knew for 1 week.

I was absolutely infatuated with this man all because he gave me a little bit of attention that I had never really gotten before.

That had to be the craziest 2 years of my life, full of emotional highs and lows, obsessive thoughts, and a fantasy relationship I created in my head.

I was so heartbroken when I finally realized I fell in love with who I wanted him to be — not who he actually was.

I had to pray my way out of that one, but I won’t say anymore about that.

Because my self-confidence was still developing during the first half of my twenties, I tolerated disrespect from the men I entertained far longer than I should've.

I remember this one time, I let a man I had known for years act like he didn't know me in front of a bunch of strangers.

Literally, one time we travelled 800 miles away to an island together, and on one of our sailboat excursions he told someone, "I'm here by myself," while I was standing right behind him, and proceeded to ignore me for the rest of the 2 hour boat tour.

He hung out on one end of the boat, and I stayed on the other.

And of course, as a quiet, quirky, inexperienced women with no boundaries and standards, I let it slide.

And even continued to let his subtle and overt ways of disrespecting me slide for 4 years after that every time he decided it was time to hang out again.

Sometimes when I think back on the utter disrespect I let slide from some of these men, I wish I could go back in time and give them a piece of my mind, but I've since learned that silence and moving on can kill a man's ego just as fine.

At the time, silent crushes, fantasy relationships, and tolerating poor behavior were all I could hope for at the time since I still lacked the confidence and the social/relational skills that could lead me to finding real love.

In fact, when I was still struggling with embracing my femininity and everything else that came with it — the shyness and social awkwardness, I used to look at the women in my life who I could tell had healthy boundaries and strong standards, and I was in awe of them.

I thought because I couldn’t get a man’s attention, and because I couldn’t seem to attract men who valued and respected me, I could never be as “picky” as these women were about the men they decided to date and eventually marry.

Not “picky” in a superficial way, but “picky” as in not willing to settle for disrespectful behavior and whatnot just to say you have a boyfriend or a husband. The good kind of picky.

But after some years of stepping into the dating field and getting the wakeup call that every inexperienced woman eventually gets when they associate themselves with the wrong type of men, I woke up one day and decided that my heart, my body, and my emotional and mental well-being were worth protecting.

And that’s when I realized that those women I so admired were not born having strong boundaries and standards — they learned from experience, just like I had to.

They became vulnerable to men who weren’t worth their time and energy, they got burned, and maybe they got burned a few times before they decided, “I don’t have to put up with this.”

The point is, I've learned a lot about this game called dating, even as "inexperienced" as I am, but I never would've learned the "big stuff" like setting boundaries, having and upholding standards, spotting red flags, and never letting a man waste your time, if I didn't get past the "small stuff" first, meaning the stuff that leads to the first date;

The stuff that was keeping me from entering the dating realm like all of my other peers.

Things like flirting/having a conversation, peaking his interest, getting a man's attention, and showing him you're interested. That “small stuff” that I’m sure many of you quiet, quirky women struggle with.

Well, if struggle with the "small stuff" (and some of the "big stuff", too, if you've made it that far), I've got something just for you!

**********************************

Introducing my first virtual workshop: Dating With Confidence (For Quiet, Quirky Women) - August 22, 2025 @6 PM - 7:30 PM CT.

This workshop is for the misfits, the late bloomers, the women who feel invisible and unlovable.

It's not about finding "the one" and it’s not about navigating the important relationship stuff that comes later on; it's about finding the courage to get started, and becoming someone who attracts the kind of attention you deserve — without having to be performative or ultra seductive, or anything like that!

Here's what you'll learn:

  • How to get a man's attention

  • How to show him you're interested

  • How to flirt without overthinking it

  • How to set boundaries, have standards, and spot the red flags before you get too attached

Whether you’re autistic, a little awkward, or just socially anxious, you will walk away knowing the skills needed to attract the right kind of attention and date with confidence!

Being quiet and quirky does not mean you don’t have your own unique flirting style.

It does not mean you don’t have sex appeal.

It does not mean you have to be a doormat and tolerate disrespect.

You’ve got what they want — you just have to believe it and act like it.

Register for the workshop today at theintrovertedmisfit.com/quirky-dating. You can also find that link in the description of this episode.

Make sure to share this episode with your quiet, quirky female friends who need to hear this message and who may need this workshop.

Connect With Caroline:

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Caroline Smith

Caroline is the founder of The Introverted Misfit, a community committed to helping socially inept people become more socially confident in themselves.

https://theintrovertedmisfit.com
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