Upcoming events
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!
Dial-Up Dating
A Virtual Dating Experience for singles 45+ that brings dating back to conversation, curiosity, and connection.
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.
Singles Pickleball Sunday
Join us for an exciting afternoon of lighthearted pickleball, laughter, and connection at SPF Chicago!
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!
Skyline Singles Soireé (50+)
Join us for the Skyline Singles Soirée, an exclusive rooftop mixer for singles 50 and over who want to connect, converse, and share an unforgettable evening in one of Chicago’s most stunning settings.
Throwback Daters Night at Activate Games Naperville (Age 45-60)
Join us for an unforgettable Throwback Dating night at Activate Games Naperville, where play meets connection!
Summer Concert Series - Sixteen Candles Band
Join Throwback Dating community members on the lawn for a Sixteen Candles Band show at Cantigny for Saturday Sun Sets.
Jazzin' at the Shedd
Join Throwback Dating community members for a fun night of live jazz, scenic views of Chicago, connection, and Navy Pier fireworks.
Train at Ravinia
Join Throwback Dating community members on the lawn at Ravinia for a picnic and to see Train perform!
Blues Traveler & Gin Blossoms at Ravinia
Join Throwback Dating community members on the lawn at Ravinia for a picnic and to see Blues Traveler perform!
July Rooftop Singles Mixer
Join us for a fun and social night on the rooftop at AZUL, exclusively for singles ages 40–60!
TopGolf Naperville
Join us for a fun and social night at TopGolf Naperville, exclusively for singles ages 45–60!
Chicago at Ravinia
Join Throwback Dating community members on the lawn at Ravinia for a picnic and to see Chicago perform!
Scenic Walk in Highland Park
Join Throwback Dating community members for a relaxing walk and talk in Highland Park.
Singles Mixer (Age 40-60)
A fun, low-pressure mixer for singles 40+ to connect, laugh, and celebrate dating again—no apps, just real people.
Throwback Field Trip: 16 Candles Band at Wells Street Art Fest
Join Throwback Dating community members at the Wells Street Art Fest and rock out to the 80's with 16 Candles Band!
Live Band Karaoke
Join Throwback Dating community members at Bub City for some Live Band Karaoke and fun!
DIAL UP DATING: First Date Best Practices for Singles Over 40 (virtual)
First dates don’t have to be awkward. Join us for tips + real talk on building connection from the start. Singles 40+ welcome!
A Singles Game Night (Rescheduled)
Come join us for a fun night of mixing, matching, and playing games with other singles - it's going to be a blast!
Pickleball at SPF
Ready to meet new people and try something fun? Join us for an exciting afternoon of lighthearted pickleball and connection at SPF.
Rooftop Singles Mixer (Age 40-60)
This isn’t just another singles event. It’s a community where dating over 40, isn’t something to stress over—it’s something to celebrate.
Let’s Be Real: A Candid Conversation Between Men & Women
A candid conversation between men and women about their experiences in today's modern dating world so that we can begin to heal the divide.
Sushi & Stand Up (Age 40-55)
Join us for some laughs at Second City followed by sushi dinner in Old Town with a group of amazing singles from Chicago.
Singles Mixer (Age 40-60)
Mingle with other high-quality singles from the Chicago area in a relaxed and welcoming atmosphere.
Rock for a Cause: The Generations' Benefit Concert
Join Throwback Dating March 28th at Sideouts for live music, drinks & merch—all to support NAMI & mental health awareness!
Sip & Scene: Award-Winning Cinema & Conversation (Singles Age 50+)
Join us for Sip & Scene as we chat about the award-winning film "A Complete Unknown" over drinks and good company!
Rock Out with Electro Retro and Throwback Dating
Join Throwback Dating March 21st at Whiskey River for live music, dancing and drinks with high-quality singles over 40 from the Chicago area
how it works
STEP 1
Click the “Apply” button to complete our short questionnaire. You’ll be added to our waitlist and notified via text and email when your profile has been reviewed.
STEP 2
Once we review your application, we’ll send an invitation to schedule your Chemistry Call with Megan so she can learn about you and what you’re looking for.
STEP 3
Complete our “Compatibility Questionnaire” and then register for your first event.
STEP 4
Meet great people at our events, build new relationships, and share a connection card with anyone you’d like to stay connected with.