Intentional matchmaking. Real humans.
Lasting connections.

We see you

Welcome to

The logo features the text 'Wayward Hearts Matchmaking' with 'Wayward Hearts' in cursive and 'MATCHMAKING' in uppercase block letters on a black background.

Where we match humans, not profiles — based on shared values and interests

Start your match journey

Membership Pricing

Wayward Hearts is currently updating its membership structure.

If you are interested in becoming a paid member, please reach out through the Contact page to start a conversation. I will be in touch with details about the new membership offer shortly.

Thank you for your patience and for investing in something real.

Contact Me to Learn More

Start Your Match Journey

Wayward Hearts is matchmaking for people who are done performing and ready to be real. No apps. No algorithms. Just thoughtful, human matching based on who you actually are.

We’re lifting wayward hearts — one match at a time.

🎙️ Notes from the Matchmaker -- my podcast on love, dating, and what it actually takes to find the right person. Now on Spotify and Apple Podcasts.

Curious? Learn More...
People enjoying a picnic outdoors with a wicker basket, a box of food including fried chicken and sauces, and drinks on a blanket.

UPCOMING EVENTS

No Events Right Now

There’s nothing scheduled at the moment, but we’re working on some exciting things behind the scenes!

The truth is, you’re emotionally intelligent, a little weird, and maybe a little tired.

What We Do: Real matchmaking based on genuine compatibility.

This Intentional Matchmaking. I don’t match based on checklists. I take time to understand who you really are - your values, what drives you, what you need in partnership - and find someone who sees and celebrates that.

No judgment about your path. No pressure to fit a mold. Just authentic matching for people ready to connect deeply.

And here’s the good news:

There's a different way - one where you stop performing and start connecting. Wayward Hearts matches you based on who you really are, not who you think you should be.

WHAT MEMBERS ARE SAYING

  • "Before working with Cheryl I was on dating apps for years which led to frustration and hopelessness and very little success. She took the time to learn who I was and what I was looking for. Within a short time that led to an introduction that was thoughtful and aligned with my values. Cheryl will make dating fun again!"

    — L, Wayward Hearts Member since Oct.

  • "It's so much safer than the apps. You have no idea if the person you're talking to is who they say they are. I feel so much more comfortable doing this. Cheryl is very open and understanding to all needs and really tries to pinpoint what you're looking for in a relationship."

    — Wayward Hearts Member

  • "Our first date went really well. Very easy to talk to and you were right, we do have a lot in common. We exchanged phone numbers as we plan to continue seeing each other."

    — Wayward Hearts Member

  • "You did an awesome job matching us up! We have lots in common, especially our values and personality compatibility. My introductory date was wonderful."

    — Carol

  • I want to thank Cheryl at Wayward Hearts Matchmaking for arranging my recent introduction. My match was a beautiful lady and we had a wonderful time over breakfast together. We found we had a lot in common and were very open with each other from the start.

    Although we mutually decided that a second date was not possible due to differences in our physical activity levels, I have no regrets about the introduction. She is a true lady and I would have loved to continue getting to know her.

    Cheryl worked hard to find me a quality match and it showed.

    Reg, Wayward Hearts Member

Intentional Matchmaking.

Real Humans. Lasting Connections

Become a member or join the Free Date-a-Base

Start your match journey
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