we’re throwing it back to what dating was like before the apps.

Upscale event experiences for high-quality singles over 40 in the Chicago area.

Tired of the dating apps?

ready to meet face to face?

you’re in the right place!

Imagine this: Walking into a room filled with people in your age range—smart, engaging, with shared goals—and they’re all single.

At Throwback Dating, we bring together professionals like you at fun, activity-based events designed to spark genuine connections.

From pasta-making classes and pickleball to game nights, live music, and more, our events create a relaxed, no-pressure atmosphere where you can meet compatible singles and enjoy great conversations.

  • “Great evening for meeting new singles! Great conversation and the ability to meet people without a website.”

    Bill

  • “Megan has a knack for connecting people—it’s just part of her genius. It was a great night! Met wonderful people and I got a date with two gentleman.”

    Gina

  • “It was a wonderful event. I met tons of great people, men and women, and also had a great time. Very well organized, even inspired me to make pasta on my own.”

    Phil

  • "You show up alone but you feel like you're not alone. Everyone is so laid back that you can talk to whomever you want. It was my first singles event in my life so I felt awkward at first, but had a great time."

    Ryan

How It Works

At Throwback Dating, we do things differently.

Our simple application process helps us verify your identity and get to know you better—so we can thoughtfully curate events filled with people who share your values, lifestyle, and interests. There’s no membership fee—you simply pay for the events you'd like to attend.

We currently offer two types of events:

  • Monthly Mixers for singles ages 40 to 60

  • Community-Only Events based on shared interests or activities, exclusively for those who’ve completed our application and interview process

Every event is designed to be relaxed, welcoming, and pressure-free—creating the perfect environment for natural conversations and meaningful connections. Whether you meet a new friend or feel chemistry with someone special, you're in great company.

Have Questions?

Schedule a quick 15-minute call with Megan HERE to learn more before applying.

We’re excited to help you feel optimistic about dating again!

Upcoming events

SINGLES MIXER

Wednesday, June 18th | 6:00pm to 8:30pm

Divan - 868 N Franklin St, Chicago

SCENIC WALK IN HIGHLAND PARK

Saturday, June 28th | 11:00am to 12:00pm

Highland Park Library

CHICAGO AT RAVINIA

Saturday, July 5th | 5:30pm to 7:00pm

Ravinia, Highland Park

TOPGOLF NAPERVILLE

Friday, July 11th | 5:30pm to 7:00pm

TopGolf Naperville

ROOFTOP SINGLES MIXER

Wednesday, July 16th | 6:00pm to 8:30pm

TBD

BLUES TRAVELER & GIN BLOSSOMS AT RAVINIA

Saturday, July 26th | 6:00pm

Ravinia, Highland Park

TRAIN AT RAVINIA

Saturday, August 2th | 7:00pm

Ravinia, Highland Park