✨ Speed Dating in Chicago | Ages 25–39 | MyCheekyDate

Chic, low-key, host-led speed dating for Chicago singles ages 25–39 who value humor and personality.

Overview
Looking for something different to do in Chicago? MyCheekyDate hosts chic, low-key speed dating for Chicago singles who value humor and personality. No loud bars, no name tags, no awkward setups, just a relaxed, host-led evening and a proper conversation with everyone you’re there to meet.

What to expect

• An evening of 16 to 40 Chicago singles, depending on the evening
• Six-to-seven-minute dates with everyone you’re there to meet
• A friendly, attentive host to guide the evening
• Age group: 25–39

The Smart-Card: chemistry, measured in the room
No algorithm decides who sits across from you. You meet everyone face to face, and your MyCheekyDate Smart-Card captures what actually happened. It’s a private card that opens from a link on your phone, with no app needed. Add a photo if you like, write a short bio on the night, and after each date quietly rate your interest on five levels. Finalize your picks by midnight. When it’s mutual, it’s a match. Your ratings stay completely private; not even our hosts can see them.

It works: an 86% match rate, an average of 2.3 matches per evening, and guests are 77% more likely to match at their second evening.

The Chicago connection
Looking for things to do in Chicago or a date night in Chicago that beats another round of swiping? Whether you live in the West Loop, Lincoln Park, Wicker Park or Logan Square, or you’re new to town and want to meet new people in Chicago, you’ll sit down with singles who share your sense of humor. Come for a Saturday night in the West Loop and leave with real conversations.

Venue
Recess, 838 W Kinzie St, Chicago, IL 60642. Every venue is chosen for its atmosphere, privacy and comfort.

One evening, three ways in
This evening is hosted together with Relish and TheCitySet. MyCheekyDate brings people who value humor and personality, Relish brings graduates and career-minded professionals, and TheCitySet brings locals who love their city. It’s one event, so you only need one ticket.

The Cheeky Circle
Guests who stand out, noticed by our hosts and fellow daters for being kind, engaging and genuine, are invited into the Cheeky Circle, our free, invite-only community. It can’t be applied for or bought. Members are first on the guest list and receive complimentary invitations across the Constellation.

The Cheeky Guarantee
If we cancel or reschedule, you may request a full refund directly from us. If your plans change, with five days’ notice or five seconds, your ticket never expires. Eventbrite’s “no refunds” notice only means we can’t refund an evening because you didn’t meet someone; no one can guarantee chemistry. For anything else, contact us directly: info@mycheekydate.com

Prefer to be introduced?
Curated Introductions is our matching system, not a matchmaker: one compatibility questionnaire, your score with every match, and a date we arrange. Introductions come from the Cheeky Circle and fellow clients, from $695. mycheekydate.com

Part of the Constellation
MyCheekyDate is part of the Constellation, seven in-person brands hosting evenings since 2007 in 50+ cities:

• MyCheekyDate: dating for people who value humor and personality
• Relish: elevated, structured dating for graduates and career-minded professionals
• TheCitySet: dating for locals who love their city
• Fancy-A-Go: dating set inside an experience
• The Gild Society: a private dating club by application
• MyCheekySocial: making new friends (not dating)
• NetworkNite: speed networking (not dating)

The standouts from every brand are invited into its circle, and Luvo Matchmaking introduces from all of them, plus The Gild Society. Chosen by the room. Introduced by Luvo. luvomatchmaking.com/the-constellation

Join us in Chicago, where being lovely has its perks.