Throwback Dating

Throwback Dating Skip the swipe. Real people. Curated events. Genuine connection. 👇 Apply to join. We're throwing it back to what dating was like before the apps!

Find your type... organically. ❤️ Throwback Dating is a vetted singles community for people in their 50s & 60s who are done with the apps and ready for something real. Community experiences for professional, quality singles over 40 in Chicagoland. If you didn't plan to be single at this age and you find that the dating world is very different now... we get it. We are bringing the fun and human con

nection back to dating - the way it used to be. Attend a few of our events, meet great people, and join our community to get access to all of our experiences. There's no pressure. Connect organically and build friendships that could turn into something more. Founder: Megan Wessels

06/02/2026

A community of vetted singles in their 50s and 60s who are tied of the dating apps and looking for real connection ❤️

Sound like you? Head to our website and fill out our short form to join for free.

05/31/2026

Throwback Daters hit the beach yesterday for a cleanup along Lake Michigan. Good weather, good people, and we left it cleaner than we found it! ✨



05/19/2026

Eden and Jack’s story gives singles over 50 hope… proof that it’s possible to find love at any age 🩷

This is your sign to give Throwback Dating a try.


Join us on Tuesday, May 19th at 7pm CST for this powerful, free Masterclass with Megan Wessels and hypnotherapist, Mina ...
05/18/2026

Join us on Tuesday, May 19th at 7pm CST for this powerful, free Masterclass with Megan Wessels and hypnotherapist, Mina Yang.

We will take a look at the beliefs that are affecting your dating experience and reprogram them with a hypnotherapy session.

Tuesday, May 19th, 2026
7:00pm CST
Save Your Spot -
https://www.msmeganwessels.com/how-to-date-over-50
❤️ Megan & Mina

04/28/2026

Our latest event at Activate Games Naperville was a blast! We kicked things off next door to connect, and once the games began, we were like kids again... running, jumping, and solving puzzles together. Everyone LOVED it.



04/17/2026

Throwback Daters took over Broken Earth Winery in Long Grove for an epic game night... and yes, it was exactly as fun as it sounds.

We bluffed our way through Taboo, got surprisingly competitive during Scattergories, tested our 80s pop culture knowledge with Pictionary, and may have let the Blackjack table determine who was buying the next glass of cabernet.

Good wine, great laughs, and just the right amount of trash talk. We’ll definitely be back for round two.



03/30/2026

When you come to one of our events, there’s no pressure to date.

It’s like walking into a room full of people who are your friends, you just haven’t met them yet!

Sign up for your first event and see for yourself. It’s free to join!

We’re waiting to welcome you in.

❤️ Megan, Throwback Dating Founder

03/30/2026

Join Throwback Dating for an unforgettable time at Activate Games Naperville, where play meets connection!

Sunday, April 26th at 12:30pm
(suggested age 45-60)

Head to THROWBACKDATING.COM and join for free!



03/29/2026

Even though there was a chill in the air, Throwback Daters were bringing the heat on the courts at SPF in March!

From first serves to rallying at the net, it was a day of friendly competition, connection, and a few surprisingly impressive shots.

And as always… the real magic happened after the final point. We traded paddles for cocktails and continued the connection over food and drinks.

At Throwback Dating, we’re defining a new way of “dating” anchored in organic connection and friendship. There’s no pressure and no awkwardness... just fun opportunities to connect.

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