From Back Bay to Seaport, Boston pairs charm with energy. MyCheekyDate hosts boutique, host-led speed dating events designed for real conversation and connection. Curious about the local dating vibe? Explore Cheeky Thoughts: Boston Edition. Prefer something more curated? Curated Introduction Packages are available in Boston, while those seeking a more private, premium approach can explore Luxury Matchmaking, a founder-led experience built from these same real-world communities.
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OCTOBER 25TH 2026 | SPEED DATING @ AC BOSTON DOWNTOWN | AGES 32-44
Speed Dating @ AC Boston Downtown - October 25th 2026
Ages: 32-44 | 6PM
225 Albany St, Boston, MA 02118
Early Bird Admission - Ends 10/20 | $32.95
Regular Admission | $36.00
NOVEMBER 4TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 29-42
Speed Dating @ Time Out Market Boston - November 4th 2026
Ages: 29-42 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 10/30 | $32.95
Regular Admission | $36.00
NOVEMBER 14TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 25-39
Saturday Night Speed Dating @ Time Out Market Boston - November 14th 2026
Ages: 25-39 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 11/09 | $32.95
Regular Admission | $36.00
NOVEMBER 15TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 36-48
Speed Dating @ Time Out Market Boston - November 15th 2026
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 11/10 | $32.95
Regular Admission | $36.00
NOVEMBER 18TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 29-42
Speed Dating @ Time Out Market Boston - November 18th 2026
Ages: 29-42 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 11/13 | $32.95
Regular Admission | $36.00
NOVEMBER 22ND 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 32-44
Speed Dating @ Time Out Market Boston - November 22nd 2026
Ages: 32-44 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 11/17 | $32.95
Regular Admission | $36.00
NOVEMBER 28TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 25-39
Saturday Night Speed Dating @ Time Out Market Boston - November 28th 2026
Ages: 25-39 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 11/23 | $32.95
Regular Admission | $36.00
NOVEMBER 29TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 36-48
Speed Dating @ Time Out Market Boston - November 29th 2026
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 11/24 | $32.95
Regular Admission | $36.00
Boston Speed Dating, Done the Cheeky Way
MyCheekyDate hosts professionally organized speed dating events in Boston, bringing together local singles for structured, in-person conversations — no swiping, no guesswork. With over 1,900 events hosted in Boston over the past decade and more than 26,000 events across 50+ cities, each evening follows a proven, host-led format refined over nearly two decades.
Events are held in well-known neighborhoods like Back Bay and at venues such as Scholars American Bistro & Cocktail Lounge, creating a relaxed, social setting. To keep things balanced, we monitor attendance and may occasionally adjust the schedule in advance — a deliberate choice to protect the experience. Your ticket always remains valid for a future Boston event, and if you prefer not to attend a rescheduled event, you may request a refund. It’s all part of the Cheeky Guarantee - keeping things flexible and centered around a genuinely good night out.
“Very enjoyable experience in Boston! Met some great people.”
— Verified Trustpilot Review
Transparency & Trust | How Our Events Work | Managed Room Quality | Independent Reviews & Media
Considering a more personalized approach? See whether matchmaking is worth it in Boston.
The Cheeky Guarantee
If MyCheekyDate reschedules or cancels your event, you may request a full refund to your original payment method. Simply contact us directly and we’ll take care of your refund from there and make sure it gets processed. If your own plans change, your ticket remains valid as flexible credit and never expires, so you’re always welcome to reschedule for another event.