Throwback Dating
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What if you could meet singles over 45 organically... in real life? At Throwback Dating, we bring together active singles for fun, in-person experiences.
Every member is screened & our events are curated for real connection. It works - Join for free! 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
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.
This year is partnering with . to support their annual Holiday Gift Drive, serving more than 1,600 children and teens across the Chicago area.
The 80’s are calling, are you picking up? ☎️
Real people. Real connections. Don’t just take our word for it — here’s what guests had to say about their Throwback Dating experience.
A Very Throwback Thanksgiving on 11/23/25
11/11/2025
Who agrees?
11/07/2025
A night of jazz and skyline views 🎶 — here’s a glimpse of our evening at The Cliff Dwellers
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 ⚾️🧢🏟️
Don’t take yourself to seriously, lighten up!
Dating in the 90’s: 📼& 🌮
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Chicago, IL