Wayward Hearts Matchmaking

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Wayward Hearts Matchmaking

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PEI's only boutique matchmaking service. Values-based. No photos shared.

Real introductions to people worth meeting.

🎙️ Notes from the Matchmaker podcast -- now on Spotify & Apple Podcasts

🌐 waywardhearts.ca

10/08/2026

A summer on PEI. An oyster bar. A tall, dark, pirate-looking champion oyster shucker walking through the door.
No, this isn't the plot of Carley Fortune's This Summer Will Be Different. This is my late twenties.
The chemistry was instant. Everyone in the room could see it. And it was never going to be anything more than a glorious summer.
In the new episode of Notes from the Matchmaker Podcast, I tell the story. I also explain what's actually happening in your brain when attraction hits, and why that feeling was designed to fade.
Episode 5: What Chemistry Actually Is. Listen on Spotify or Apple Podcasts.

10/06/2026

October on PEI does something to you.
The red soil deepens. The leaves turn. The harvests are happening in every direction: potato fields, apple orchards, the last of the garden.
The Island slows down in the best possible way. The pace of summer gives way to something quieter and more deliberate.
It is my favourite version of this place.
There is something about autumn here that makes people reflective. About what the year has been. Who they spent it with.
If those reflections are landing somewhere familiar - you know where to find me.
waywardhearts.ca 💙

10/01/2026

When did we decide love has to hit like a lightning bolt?
Movies. Romance novels. Reality TV. We have been fed the same story over and over. If you don't feel an instant zing on the first date, it will never be there.
I don't believe that. And I have two stories from my own life that prove it.
The love of my life caught me completely off guard. He spent two months getting to know my mind before he ever leaned in. One kiss on my birthday and I swooned. I am not a swooner.
New episode of Notes from the Matchmaker is live. Chemistry Is Not a Lightning Bolt.
Listen on Spotify or Apple Podcasts. Link in comments.

09/25/2026

September on PEI has a way of making people think ahead.
The warmth is still here but you can feel the edges of it starting to soften. The days are getting shorter. You know what is coming.
And if you have spent a PEI winter alone you know exactly what I am talking about.
Winter on this Island is long and dark and beautiful in its own way. But it is a lot more beautiful when you have someone to share it with. Someone to stay in with. Someone to cook for or cook with. Someone whose car you brush the snow off because you are already outside doing yours anyway.
September is not too early to think about that person.
It is actually exactly the right time.
Visit waywardhearts.ca to learn more and join the free Date-a-Base today.
waywardhearts.ca 💙

09/21/2026

I want to tell you about the moment I probably should have realized I was going to end up becoming a matchmaker.
It was 2013. I was working overseas in international development. My colleague and I were watching two perfectly lovely people in our circle completely fail to navigate their way toward each other despite the fact that the attraction was obvious to literally everyone except them.
At some point I turned to my colleague and said "someone should open a Charm School. Teach people how to actually connect with each other."
She laughed. I laughed.
And then I went back to watching these two people not figure it out and thought about it for approximately the next ten years.
Here is what I was really saying in that moment, though I didn't have the words for it yet. People don't fail at relationships because they aren't worthy of love. They fail because nobody ever taught them how to show up for it.
That is still what I believe. It is also more or less why Wayward Hearts exists.
The Charm School finally opened. It just took a decade and a different name. 💙
waywardhearts.ca

09/18/2026

The PEI International Shellfish Festival is one of my favourite weekends of the year.
I was there for the very first one. I have loved it ever since.
Here is what happens at the Shellfish Festival. You walk in and within approximately four minutes you are happy. It is not optional. The chowder competition. The raw oysters. The Maritime music that makes it physically impossible to stand still.
And then you are watching someone dance across the room or waiting in line for another oyster and you think to yourself, I wonder if they are single.
We have all had that thought at the Shellfish Festival. Do not pretend otherwise.
The good news is that some of the most interesting single people on PEI are already in my Date-a-Base.
Just saying.
waywardhearts.ca 💙

09/16/2026

September on PEI is a secret that Islanders keep to themselves.
The summer time tourists have gone home. The lineups have disappeared. The beaches and the harbour fronts and the patios that were packed just weeks ago are filled with Islanders again.
And the Island delivers.

The light shifts in September. It turns golden in a way that makes everything look like it was meant to be photographed. The harvests are happening in the fields. The air is warm but with just enough of a hint of what is coming to make you pay attention.

We pay attention because we know. Winter is coming. Every warm day in September is a gift and Islanders treat it that way.
We get outside. We walk the beaches that are finally quiet. We linger on the patios. We stop and actually look at this place we are lucky enough to call home.

September on PEI is not the end of summer. It is summer at its most honest.

Enjoy every single day of it.
waywardhearts.ca 💙

09/14/2026

A new episode of Notes from the Matchmaker is live.
This one is about your list. You know the one. The height. The age. How They Look. The exact energy they need to bring into a room. The things you absolutely will not compromise on.
I am not here to judge your list. I have had one myself. What I want to tell you is what I actually see when you hand it to me.
Because here is the thing. A list that keeps you safe is not the same as a list that finds you someone you can be happy with.
Episode three is called Let's Talk About Your List. Give it a listen.

09/10/2026

If I could sit down with the version of myself that launched Wayward Hearts one year ago, I would say this.
Cheryl. This is going to be way more work than you think.
You are going to work until ten o'clock at night. You are going to work weekends. People are going to reach out at all hours because their loneliness does not keep business hours and neither will you, for a while.
They are going to expect you to be available whenever they are. And because you genuinely care about every single one of them you are going to try to be.
Here is what I know now that I wish I had known then.
You cannot work and be available 24/7. You cannot see people clearly when you are exhausted. You cannot do your best work for the members who are counting on you if you have not protected your own time, your own health, your own relationships.
Boundaries are not a betrayal of the people who trust you. They are what make it possible to keep showing up for them.
Establish them early. Hold them kindly but firmly. And remember that taking care of yourself is not separate from taking care of your business.
It is exactly the same thing.
waywardhearts.ca 💙

Address

PO Box 20003
Charlottetown, PE
C1A9E3

Website

https://waywardheartsmatchmaking.ca/

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