A free live masterclass for men over 50 who keep doing everything right — and still ending up alone. Join psychotherapist Dr. Ari Graff and dating coach Megan Wessels on October 14th at 7pm CST.

Join us at Aster Hall for a Throwback Daters game night, where we’ll break out crowd favorites like Scattergories and Taboo for an evening of quick wit, easy laughs, and conversation that flows without trying too hard.

Welcome to the Throwback Daters Lounge — your monthly chance to meet fellow members, get oriented in the community, and actually connect with the people you joined to meet.

Join us at TopGolf Naperville for an evening of friendly competition, easy conversation, and the kind of chemistry you definitely won’t find on a dating app.

Join Megan Wessels and George Mirov of Tru Integrative Wellness for a candid, practical conversation about men’s vitality, hormone health, and what your body may be trying to tell you.

Join us for the Skyline Singles Soirée, an exclusive rooftop mixer for singles in their 50s and 60s who want to connect, converse, and share an unforgettable evening in one of Chicago’s most stunning settings.

Welcome to the Throwback Daters Lounge — your monthly chance to meet fellow members, get oriented in the community, and actually connect with the people you joined to meet.

Join us for a morning hike through Deer Grove Forest Preserve, one of the oldest and most beautiful preserves in the Forest Preserves of Cook County.

Join us at Cindy's Rooftop for a Summer Happy Hour above the Chicago Athletic Association Hotel, with one of the city's most iconic views.

Welcome to the Throwback Daters Lounge — your monthly chance to meet fellow members, get oriented in the community, and actually connect with the people you joined to meet.

Join Throwback Daters on the lawn at the brand new Block 59 in Naperville for a night of live music with Sixteen Candles — Chicago's ultimate 80s cover band.

Stop repeating the same patterns. Join Megan & Mina live to reset your picker and finally attract the right person.

Join us for an intimate evening of small bites, beverages and good company while we pack backpacks for kids who need them most. This is connection with purpose... and honestly one of our favorite kinds of evenings.

Join us for a relaxed outdoor happy hour along the Chicago Riverwalk, where you'll connect with fellow Throwback Daters in a setting that feels easy and fun.

Join us for a walk along the Chicago lakefront, good conversation, fresh air, and easy connection along the way.

Welcome to the Throwback Daters Lounge — your monthly chance to meet fellow members, get oriented in the community, and actually connect with the people you joined to meet.

For this special Throwback Dating experience, we’ll gather in the kitchen for a hands-on cooking class led by Chef Molly Sell, where you’ll learn the art of grilling with fresh summer ingredients and bold seasonal flavors.

Join the Throwback Dating community for a group trip to Summerfest, where the journey is just as fun as the destination.

Join us for an engaging night focused on real connection, great conversation, and the possibility of something meaningful.

Join us for a walk along the Chicago lakefront, good conversation, fresh air, and easy connection along the way.

Join us for an intimate happy hour on the patio at Erie Café - one of Chicago's most charming spots to spend a summer evening.

A free live masterclass for men over 50 who keep doing everything right — and still ending up alone. Join psychotherapist Dr. Ari Graff and dating coach Megan Wessels on June 17th at 7pm CST.

Welcome to the Throwback Daters Lounge — your monthly chance to meet fellow members, get oriented in the community, and actually connect with the people you joined to meet.

Join the Throwback Dating community for a morning of fresh air, meaningful conversation, and giving back as we help clean up our beautiful Lake Michigan shoreline.

We're partnering with Tru Integrative Wellness to celebrate the grand opening of this exciting new wellness practice and we'd love for you to join us.

Stop repeating the same patterns. Join Megan & Mina live to reset your picker and finally attract the right person.

Welcome to the Throwback Daters Lounge — your monthly chance to meet fellow members, get oriented in the community, and actually connect with the people you joined to meet.

Slow Dance Dating is a thoughtfully curated, invite-only experience that blends matchmaking, guided connection, and playful human interaction... similar to speed dating, without the rush.

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

Join us at the beautiful Broken Earth Winery for a relaxed evening designed especially for singles age 55 and better who enjoy good company, great wine, and a little friendly competition.