Upcoming events
Singles In Service: Back To School Backpack Drive (NORTH)
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.
How to Date Over 50, Masterclass Series - We’re Gonna Fix Your Picker (VIRTUAL)
Stop repeating the same patterns. Join Megan & Mina live to reset your picker and finally attract the right person.
Rock The Block with 16 Candles (WEST)
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.
Throwback Daters Lounge (VIRTUAL)
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.
Sounds of Summer: Hairbangers Ball at Cantigny (WEST)
Join the Throwback Dating crew on the lawn at the beautiful Cantigny Park in Wheaton for a night of 80s hair rock with Hairbangers Ball — Chicago's own "Best Rock Band" and one of the most sought-after 80s Hair Rock tribute bands in the country.
Summer Happy Hour at Cindy's Rooftop (Chicago)
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.
How to Date Over 50, Masterclass Series - Dress to Impress: A Men's Style Guide for Dating Over 50 (VIRTUAL)
Join Megan & Rachel live to know how to show up as the most confident version of you... because how you dress on the outside affects how you feel on the inside.
Morning Hike at Deer Grove Forest Preserve (NORTH)
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.
Happy Hour on the Riverwalk (CHICAGO)
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.
Lakefront Walk (CHICAGO)
Join us for a walk along the Chicago lakefront, good conversation, fresh air, and easy connection along the way.
Throwback Daters Lounge (VIRTUAL)
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.
Singles Culinary Class - Elevate Your Summer Grilling (WEST)
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.
Singles Group Trip To Summerfest (NORTH)
Join the Throwback Dating community for a group trip to Summerfest, where the journey is just as fun as the destination.
Over 50 First Dates (WEST)
Join us for an engaging night focused on real connection, great conversation, and the possibility of something meaningful.
Lakefront Walk (CHICAGO)
Join us for a walk along the Chicago lakefront, good conversation, fresh air, and easy connection along the way.
Summer Happy Hour at Erie Café Patio (CHICAGO)
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.
How to Date Over 50 - You're Too Nice & It's Killing Your Love Life (virtual)
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.
Throwback Daters Lounge (VIRTUAL)
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.
Singles in Service: Beach Clean-Up
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.
Throwback Dating x Tru Integrative Wellness
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.
How to Date Over 50 - We’re Gonna Fix Your Picker
Stop repeating the same patterns. Join Megan & Mina live to reset your picker and finally attract the right person.
Throwback Daters Lounge
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
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.
Singles Play At Activate Games Naperville
Join us for an unforgettable Throwback Dating night at Activate Games Naperville, where play meets connection!
Singles Wine & Game Night
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.
Dial-Up Dating
A Virtual Dating Experience for singles 45+ that brings dating back to conversation, curiosity, and connection.
Singles Pickleball Sunday
Join us for an exciting afternoon of lighthearted pickleball, laughter, and connection at SPF Chicago!
An Evening of Visionary Awareness at the Art Institute of Chicago
Join us for a guided tour of contemporary art in the Modern Wing of the Art Institute of Chicago.
Dial-Up Dating
A Virtual Dating Experience for singles 45+ that brings dating back to conversation, curiosity, and connection.
80's Night with Sixteen Candles Band
Join Throwback Dating for an all out 80's dance party with Sixteen Candles at the House of Blues!
Slow Dance Dating
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.
Fit For Love in ‘26
If you want 2026 to be the year you feel healthier, lighter, stronger, more energized, and more magnetic... this is for you.
Dial-Up Dating
A Virtual Dating Experience for singles 45+ that brings dating back to conversation, curiosity, and connection.
Singles In Service: Holiday Gift Wrapping with Kids Above All
Join Throwback Dating’s Singles In Service to make the season brighter for kids in need.
A Very Throwback Thanksgiving
Come and get to know the members of the Throwback Dating community and have a blast before the holidays!
Throwback Daters Fall Dinner & Wine Pairing In Highland Park (Age 48-65)
A cozy Throwback Daters evening in Highland Park.
Live Jazz on the Cliff: An Evening with Throwback Daters (Age 50+)
Meet fun singles who love jazz and Chicago!
Throwback Daters Night Out: Cubs vs. Mets at Wrigley Field (Age 50-65)
Meet fun singles who love baseball and Chicago!
how it works
STEP 1
Click the “Apply” button and complete our short application. Every applicant is personally reviewed — because the quality of your experience starts with the quality of the people in the room.
STEP 2
Once approved, you'll have two options: schedule a Chemistry Call with Megan for a personal conversation, or fill out our Compatibility Questionnaire. Either way, this helps Megan build your profile and find the right matches for you.
STEP 3
After completing your Chemistry Call or Compatibility Questionnaire, you'll choose the membership that fits where you are right now — from pay-per-event all the way to our full Concierge Experience where Megan personally curates your introductions and walks alongside you every step of the way.
STEP 4
Register for your first event, connect with members in the community, and let things unfold naturally. That's the throwback way.