Throwback Dating
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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 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
08/24/2026
Upcoming Throwback Dating events for active singles in their 50s and 60s in the Chicago area!
Morning Hike - August 29th, West Dundee Road
👉 https://www.throwbackdating.com/upcoming-events/260829-morning-hike
Skyline Singles Soirée - September 10th, Chicago
👉 https://https://www.throwbackdating.com/skyline-singles-soiree
Pascal gets it. (One of Chicago’s favorite Golden Bachelors)
Meeting someone after 50 isn’t as easy as it used to be — especially if dating apps aren’t your thing.
That’s exactly why I created Throwback Dating.
We bring together single men and women in their 50s & 60s who actually want to meet in real life — in a fun, comfortable environment where starting a conversation doesn’t feel awkward.
And as Pascal says… you have a chance to meet people in your age group. 🙌
Our Skyline Singles Soirée is coming up on September 10th in Chicago, and Early Bird tickets for MEN end this Sunday.
After that, men’s tickets move to invite only.
Skip the swipe. Come meet someone the old-fashioned way. ❤️
👉 Grab your ticket before Sunday here:
https://www.throwbackdating.com/skyline-singles-soiree
This is not your normal singles mixer.
We curate the guest list with people you’ll want to meet. Elevated, professional… people who invest in their appearance and their growth.
No grandma/grandpa vibes 😉
There are a few Early Bird tickets left for men… then it’s invite only.
Grab your ticket before Sunday here:
https://www.throwbackdating.com/skyline-singles-soiree
08/17/2026
Upcoming Throwback Dating events for active singles in their 50s and 60s in the Chicago area!
Cindy’s Rooftop - August 20th, Chicago
👉 https://www.throwbackdating.com/upcoming-events/260813-happy-hour
Morning Hike - August 29th, West Dundee Road
👉 https://www.throwbackdating.com/upcoming-events/260829-morning-hike
How do you stop wasting time on people who aren't a fit? Jack found his answer... no more speed dating, no more apps, no more years of "nope, doesn't work." Just real vetting, done for you, before you ever meet. That's the Concierge Experience.
❤️ Megan, Your Dating Concierge
Learn more here - https://www.throwbackdating.com/concierge
Concierge Experience | Matchmaker for men over 50 | Dating Concierge | Dating over 50 | Dating app alternative | Chicago matchmaker | Client testimonial | Skip the swipe | Offline Dating
Wondering what it’s like at a Throwback Dating event? Let Phil break it down.
We build our events to feel comfortable and welcoming from the moment you walk in. Come see why offline dating makes all the difference. ❤️
08/03/2026
Upcoming Throwback Dating events for active singles in their 50s and 60s in the Chicago area!
Hairbangers Ball - August 8th, Wheaton
👉 https://www.throwbackdating.com/upcoming-events/260808-hairbangers-ball
Cindy’s Rooftop - August 13th, Chicago
👉 https://www.throwbackdating.com/upcoming-events/260813-happy-hour
08/03/2026
sixteencandlesband at Rock the Block in Naperville was a blast!
We rocked the block to all the best 80s hits with 16 Candles! 🎸⚡️ Singing along to live music hits different with our amazing community of singles.
Next up: Hairbangers Ball live on August 8th.
👉 https://www.throwbackdating.com/upcoming-events/260808-hairbangers-ball
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Chicago, IL