✨ Speed Dating in Boston | Ages 36-48 | MyCheekyDate

Chic, host-led speed dating for Boston singles aged 36-48 who value humor and personality, at Time Out Market Boston on Sunday, November 8.

Overview
Looking for something different to do in Boston? MyCheekyDate hosts chic, low-key speed dating for Boston 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 Boston 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: 36–48

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 Boston connection
Now that the clocks have gone back and the evenings come early, a Sunday date night in Boston beats another night in. Whether you’re coming from Chinatown, Mission Hill, Newton, Watertown or Medford, you can spend a relaxed evening meeting new people in Boston, with a host who keeps the conversation moving. It’s one of the easier things to do in Boston for singles who like their evenings warm, unhurried and quiet enough to talk.

Venue
Time Out Market Boston, 401 Park Dr, Boston, MA 02215. 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 Boston, where being lovely has its perks.