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 Luvo Matchmaking, a founder-led experience built from these same real-world communities.
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JUNE 13TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 24-38
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Time Out Market Boston - June 13th 2026
Ages: 24-38 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/08 | $32.95
Regular Admission | $36.00
JUNE 17TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 25-39
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Speed Dating @ Time Out Market Boston - June 17th 2026
Ages: 25-39 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/12 | $32.95
Regular Admission | $36.00
JUNE 20TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 32-44
Saturday Night Speed Dating @ Time Out Market Boston - June 20th 2026
Ages: 32-44 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/15 | $32.95
Regular Admission | $36.00
JUNE 21ST 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 36-48
Speed Dating @ Time Out Market Boston - June 21st 2026
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/16 | $32.95
Regular Admission | $36.00
JUNE 27TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 24-38
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Time Out Market Boston - June 27th 2026
Ages: 24-38 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/22 | $32.95
Regular Admission | $36.00
JULY 1ST 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 25-39
Speed Dating @ Time Out Market Boston - July 1st 2026
Ages: 25-39 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/26 | $32.95
Regular Admission | $36.00
JULY 4TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 32-44
Saturday Night Speed Dating @ Time Out Market Boston - July 4th 2026
Ages: 32-44 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/29 | $32.95
Regular Admission | $36.00
JULY 5TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 36-48
Speed Dating @ Time Out Market Boston - July 5th 2026
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 06/30 | $32.95
Regular Admission | $36.00
JULY 11TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 24-38
Saturday Night Speed Dating @ Time Out Market Boston - July 11th 2026
Ages: 24-38 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 07/06 | $32.95
Regular Admission | $36.00
JULY 15TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 25-39
Speed Dating @ Time Out Market Boston - July 15th 2026
Ages: 25-39 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 07/10 | $32.95
Regular Admission | $36.00
JULY 18TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 32-44
Saturday Night Speed Dating @ Time Out Market Boston - July 18th 2026
Ages: 32-44 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 07/13 | $32.95
Regular Admission | $36.00
JULY 19TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 36-48
Speed Dating @ Time Out Market Boston - July 19th 2026
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 07/14 | $32.95
Regular Admission | $36.00
JULY 25TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 24-38
Saturday Night Speed Dating @ Time Out Market Boston - July 25th 2026
Ages: 24-38 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 07/20 | $32.95
Regular Admission | $36.00
JULY 29TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 25-39
Speed Dating @ Time Out Market Boston - July 29th 2026
Ages: 25-39 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 07/24 | $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.