The Dating Concierge who tells you the truth — and stays until things actually change.
Dating after 50 is different. The history is deeper. The stakes feel higher. And the rulebook nobody gave you when you were younger?
It doesn't exist at this stage of life.
That's where I come in.
WHAT’S A DATING CONCIERGE?
It's a title you've probably never heard... and that's the point. What I do didn't really exist before.
A matchmaker hands you names from a database. A coach hands you homework and tells you to "put yourself out there." I do something different... and far more personal.
Like the best concierge you've ever had, I get to know exactly what you're looking for, and then I make it happen... with taste, with care, and with a vetted community of wonderful people you'd never find on your own. I personally introduce you to people I believe could be your person, and I tell you why. After your dates, I gather honest feedback from both sides and use it to help you show up even more as yourself next time... not a polished, careful version, but the real you. And I stay beside you through all of it, until you find what you're looking for.
It's warm. It's hands-on. And honestly... it's a lot more fun than doing this alone.
MEGAN’S STORY
I spent years watching smart, successful, genuinely wonderful people struggle with dating, not because they weren't enough, but because they were bringing old patterns into a new chapter of life without realizing it.
I know that story personally. I've lived it.
I'm Megan Wessels - Dating Concierge and the founder of Throwback Dating — a curated community for singles in their 50s and 60s in Chicago and beyond. Over the past several years I've sat across from hundreds of incredible men and women in Chemistry Calls, listened to what's really going on beneath the surface, and helped real people get out of their own way and closer to finding their person.
What I've learned is this: most people who are struggling with dating aren't struggling because something is wrong with them. They're struggling because they're showing up to this chapter of life with patterns, habits, and blind spots they developed decades ago, and nobody has ever held up a mirror and said "here's what's actually happening."
I'm that mirror. But a kind one.
My concierge service isn't about becoming someone different. It's about becoming more of who you already are. The parts that got buried under decades of doing, achieving, and surviving.
Those parts are still there. And they're exactly what someone is waiting to fall in love with.
IN THE MEDIA
WGN MORNING NEWS
Dating Tips for Singles Over 50
IN MY HOMETOWN PODCAST
How to Find Love Without Apps
NPR CHICAGO
Finding Love and Companionship Later in Life
I talked with NPR Chicago's In the Loop with Sasha-Ann Simons about love, connection, and what's actually getting in the way for singles over 50.
You'll also get to meet Eden and Jack, a couple in their 70s who found each other through Throwback Dating. We’ll talk about their story and what finding love later in life actually takes.
“He’s an answer to my prayers.”
— Eden
MY APPROACH
Warm and Honest
I'm not here to tell you what you want to hear. I'm here to tell you what will actually help with kindness, without judgment, and always with your best interests at heart.
Practical and Personal
This isn't therapy and it isn't a lecture. It's a real conversation between two adults and one of whom has spent years inside the dating world for singles 50+ and knows exactly what's working and what isn't.
Pattern-focused
Most dating struggles aren't about the people you're meeting. They're about the patterns you're repeating. My work helps you see those patterns clearly and gives you real tools to change them.
Rooted in Community
As the founder of Throwback Dating, I'm connected to a real, active community of vetted singles in Chicago and beyond. My clients benefit from that world in ways that no dating coach can offer.
WHO I WORK WITH
I serve two groups of people, and I've built a dedicated space for each:
For women who are ready to reconnect with the most magnetic version of themselves:
For men who are ready to lead with confidence and find their person:
Not sure where to start?
Let's just talk.
A relaxed, no-pressure conversation to talk about where you are and whether the Concierge Experience is the right next step.
❤️ Megan