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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SEPTEMBER 12TH 2026 | SATURDAY NIGHT SPEED DATING @ AC BOSTON DOWNTOWN | AGES 24-38
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ AC Boston Downtown - September 12th 2026
Ages: 24-38 | 7PM
225 Albany St, Boston, MA 02118
Early Bird Admission - Ends 09/07 | $32.95
Regular Admission | $36.00
SEPTEMBER 13TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 32-44
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Speed Dating @ Time Out Market Boston - September 13th 2026
Ages: 32-44 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 09/08 | $32.95
Regular Admission | $36.00
SEPTEMBER 19TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 25-39
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Time Out Market Boston - September 19th 2026
Ages: 25-39 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 09/14 | $32.95
Regular Admission | $36.00
SEPTEMBER 20TH 2026 | SPEED DATING @ AC BOSTON DOWNTOWN | AGES 36-48
Speed Dating @ AC Boston Downtown - September 20th 2026
Ages: 36-48 | 6PM
225 Albany St, Boston, MA 02118
Early Bird Admission - Ends 09/15 | $32.95
Regular Admission | $36.00
SEPTEMBER 23RD 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 29-42
Speed Dating @ Time Out Market Boston - September 23rd 2026
Ages: 29-42 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 09/18 | $32.95
Regular Admission | $36.00
SEPTEMBER 26TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 24-38
Saturday Night Speed Dating @ Time Out Market Boston - September 26th 2026
Ages: 24-38 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 09/21 | $32.95
Regular Admission | $36.00
SEPTEMBER 27TH 2026 | SPEED DATING @ TIME OUT MARKET BOSTON | AGES 32-44
Speed Dating @ Time Out Market Boston - September 27th 2026
Ages: 32-44 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 09/22 | $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.