Whether in the candlelit corners of Back Bay or the buzzing bars of Seaport, Boston brings its own blend of charm and curiosity. MyCheekyDate hosts boutique-style, host-led speed dating events across the city — designed for genuine conversation, laughter, and a touch of cheeky New England spirit. Curious about the Boston dating vibe? Explore our Cheeky Thoughts: Boston Edition. Prefer curated one-to-one introductions? Explore Curated Introduction Packages are in Boston.
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MARCH 14TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET BOSTON | AGES 32-44
*SOLD OUT - Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Time Out Market Boston - March 14th 2026
Ages: 32-44 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 03/09 | $34.95
Regular Admission | $38.00
MARCH 21ST 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 24-38
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - March 21st 2026
Ages: 24-38 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 03/16 | $34.95
Regular Admission | $38.00
MARCH 22ND 2026 | SATURDAY NIGHT SPEED DATING @ AC BOSTON DOWNTOWN | AGES 36-48
Speed Dating @ AC BOSTON DOWNTOWN - March 22nd 2026
Ages: 36-48 | 6PM
225 Albany St, Boston, MA 02118
Early Bird Admission - Ends 03/17 | $32.95
Regular Admission | $36.00
MARCH 28TH 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 32-44
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - March 28th 2026
Ages: 32-44 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 03/23 | $32.95
Regular Admission | $36.00
APRIL 4TH 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 24-38
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - April 4th 2026
Ages: 24-38 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 03/31 | $32.95
Regular Admission | $36.00
APRIL 11TH 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 32-44
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - April 11th 2026
Ages: 32-44 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 04/06 | $32.95
Regular Admission | $36.00
APRIL 18TH 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 24-38
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - April 18th 2026
Ages: 24-38 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 04/13 | $32.95
Regular Admission | $36.00
APRIL 25TH 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 32-44
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - April 25th 2026
Ages: 32-44 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 04/20 | $32.95
Regular Admission | $36.00
Boston Speed Dating, Done the Cheeky Way
MyCheekyDate’s Boston speed dating events are hosted in real venues across the city, led by a friendly host, and designed for genuine, face-to-face conversation — no apps, no awkward games. Tickets are purchased through Eventbrite (as shown on your receipt and card statement). After the event, guests submit selections through our Smart-Card system, and mutual matches unlock next steps. Simple process, real people, very Boston.
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