Throwback Dating

Throwback Dating A social club for singles in their 40s, 50s, 60, even 70s in the Chicago area. Meet organically and see if there is a vibe before you connect.

No pressure, no awkwardness. Just a great community of people who are like-minded, single, and love to have fun. We're throwing it back to what dating was like before the apps! 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 connection 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

12/11/2025

By far this was our most loved event. It feels so good to do good. Thank you to the team at for creating such a wonderful, connection experience for us.

12/03/2025

This year is partnering with . to support their annual Holiday Gift Drive, serving more than 1,600 children and teens across the Chicago area.

11/18/2025

The 80’s are calling, are you picking up? ☎️

11/17/2025

Real people. Real connections. Don’t just take our word for it — here’s what guests had to say about their Throwback Dating experience.

11/13/2025

A Very Throwback Thanksgiving on 11/23/25

Who agrees?
11/11/2025

Who agrees?

A night of jazz and skyline views 🎶 — here’s a glimpse of our evening at The Cliff Dwellers ...
11/07/2025

A night of jazz and skyline views 🎶 — here’s a glimpse of our evening at The Cliff Dwellers

Take us out to the ball game! Our Throwback crew hit the stands for a night of baseball, city views, and new connections...
11/04/2025

Take us out to the ball game! Our Throwback crew hit the stands for a night of baseball, city views, and new connections at Wrigley ⚾️🧢🏟️

11/03/2025

Don’t take yourself to seriously, lighten up!

10/28/2025

Dating in the 90’s: 📼& 🌮

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Chicago, IL

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