The reason dating sucks is because you were never taught how.

Hi, I'm Kate! As an executive assistant and former sugar baby, I help men who

For a decade, I lived in a world where relationships were anything but honest. What I learned is that real connection can't be bought—it can only be built. Now, I coach men and women to date with clarity, confidence, and authenticity, so they can attract meaningful relationships—the right way.

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The Reason You Suck at Dating is Because You Were Never Taught How

The Reason You Suck at Dating is Because You Were Never Taught How

You're stuck in a fruitless relationship cycle for one of these four reasons (and sometimes, it's more than one).

You're stuck in a fruitless relationship cycle for one of these four reasons (and sometimes, it's more than one).

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Dating Coaching for Ambitious Men

It's as easy as 1- 2-3.

It's as easy as 1- 2-3.

YOU:

Incredibly successful. You have almost everything you want and you enjoy it. The patterns and habits that have gotten you to this point in your life have served you well. But you’re sick of the same day-in, day-out routine: waking up, rolling over to check your stocks, getting out of bed only to drink your coffee and spend your day alone, throwing yourself into work to escape the monotony; longing for real connection, and struggling to find it.

ME:

Your literal wing woman, helping you gain the skills and know-how to attract the relationship you want and to keep it. It’s time for interesting conversations. And it’s time to stop dating. Once and for all. Your time is the most precious commodity you have. Let’s stop wasting

Dating Coaching for Ambitious Men

Dating Coaching for Ambitious Men

You: Incredibly successful. You have almost everything you want and you enjoy it. The patterns and habits that have gotten you to this point in your life have served you well. But you’re sick of the same day-in, day-out routine: waking up, rolling over to check your stocks, getting out of bed only to drink your coffee and spend your day alone, throwing yourself into work to escape the monotony; longing for real connection, and struggling to find it.


Me: Your literal wing woman, helping you gain the skills and know-how to attract the relationship you want and to keep it. It’s time for interesting conversations. And it’s time to stop dating. Once and for all. Your time is the most precious commodity you have. Let’s stop wasting it.

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Dating Coaching for Ambitious Men

Dating Coaching for Ambitious Men

Dating Coaching for Ambitious Men

You: Incredibly successful. You have almost everything you want and you enjoy it. The patterns and habits that have gotten you to this point in your life have served you well. But you’re sick of the same day-in, day-out routine: waking up, rolling over to check your stocks, getting out of bed only to drink your coffee and spend your day alone, throwing yourself into work to escape the monotony; longing for real connection, and struggling to find it.


Me: Your literal wing woman, helping you gain the skills and know-how to attract the relationship you want and to keep it. It’s time for interesting conversations. And it’s time to stop dating. Once and for all. Your time is the most precious commodity you have. Let’s stop wasting it.

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Here's Why You're Single

Here's Why You're Single

You're stuck in a fruitless relationship cycle for one of these four reasons (and sometimes, it's more than one).

You're stuck in a fruitless relationship cycle for one of these four reasons (and sometimes, it's more than one).

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Clarity

You don’t know what you want.


If your dating life feels aimless, it’s likely because you haven’t defined your non-negotiables and relationship goals.


How we fix it: Get clear on your values, dealbreakers, and what a fulfilling relationship looks like for you.

Confidence

Communication

Connection

Here's What You Can Do About It

Here's What You Can Do About It

It's time to unlock your full dating potential.



It's time to unlock your full dating potential.



Here's What You Can Do About It

Here's What You Can Do About It

It's time to unlock your full dating potential.



It's time to unlock your full dating potential.



How Coaching Works

It's as easy as 1- 2-3.

It's as easy as 1- 2-3.

Step 1

Decide

The first step starts with a choice: You’re ready to approach dating differently—with clarity, confidence, and purpose. That decision alone is a powerful turning point. If that feels true for you, I invite you to fill out the form below. It's a valuable reflection exercise and will allow us to make sure we’re the right fit to work together.

Step 2

Dive Deep

I’ll reach out to you to schedule a free 30-minute introduction call. You can expect a private, judgment-free conversation where we’ll take a deep dive into your dating life—what’s been holding you back, what you truly want in a partner, and how you can start showing up with more confidence, clarity, and intention.

Step 3

Date Differently

If you’re happy with your introductory call, we’ll continue working together over the next three months, uncovering the real roots of what’s keeping you stuck—old narratives, unhelpful patterns, unconscious fears—and replacing them with new lines of thinking that reflect who you actually are. This is where the real transformation happens: when you learn the mindset shifts and develop the practical tools that move you forward—on your terms, based in truth, and not performance.. No more spinning in circles. No more second-guessing. Are you ready to date differently?

Your Questions, Answered

Your Questions, Answered

Interested in working together? Start here for answers to the most asked questions!

Interested in working together? Start here for answers to the most asked questions!

What is a dating coach, exactly?

Why should I hire a dating coach? Can’t I figure this out on my own?

Isn’t hiring a dating coach embarrassing? Won’t people judge me for needing help?

Will this actually work for me? What if I don’t see results?

That all sounds great. But how much is it?

Are you still a sugar baby?

Happy Clients

Happy Clients

Here's what some of my wonderful clients have to say about what it's like to work with me.

Here's what some of my wonderful clients have to say about what it's like to work with me.

Contact Section Image
Contact Section Image
Contact Section Image

Let's Chat!

Let's Chat!

Let's Chat!


Thank you for considering working with me! It tells me you're interested in your own self-development and growth. That alone is a reason to celebrate. If you're rady to make dating fun, simple, and easy, I ask that you fill out the form below, as it's designed to help me understand whether we’d be a great fit to work together (and as a bonus, it’s also a great self-reflection exercise). I only work with a small number of clients at a time to ensure I can give each person my full energy and attention. If you're curious, open, and committed to your growth, you’re already in the right place. Thank you for considering this work—I look forward to seeing what we can build together :).

Contact Section Image
Contact Section Image
Contact Section Image

Let's Chat!

Let's Chat!

Let's Chat!


Thank you for considering working with me! It tells me you're interested in your own self-development and growth. That alone is a reason to celebrate. If you're rady to make dating fun, simple, and easy, I ask that you fill out the form below, as it's designed to help me understand whether we’d be a great fit to work together (and as a bonus, it’s also a great self-reflection exercise). I only work with a small number of clients at a time to ensure I can give each person my full energy and attention. If you're curious, open, and committed to your growth, you’re already in the right place. Thank you for considering this work—I look forward to seeing what we can build together :).

© 2025 The Dating Fairy.

+1 (647) 485-3558

kate@thedatingfairy.com

33 Bloor Street E, Toronto, ON, M4W 3H1. By appointment only.

© 2025 The Dating Fairy.

visit: 33 Bloor Street W, Toronto, ON, M4W 3H1

By appointment only.

ring: +1 (647) 485-3558

write: hello@thedatingfairy.com

© 2025 The Dating Fairy.

visit: 33 Bloor Street W, Toronto, ON, M4W 3H1

By appointment only.

ring: +1 (647) 485-3558

write: hello@thedatingfairy.com