Whether in the candle-lit 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 — the perfect setting for genuine conversation, laughter, and a touch of cheeky New England spirit.
DECEMBER 13TH 2025 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET | AGES 24-36
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Time Out Market - December 13th 2025
Ages: 24-36 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 12/8 | $34.95
Regular Admission | $38.00
DECEMBER 14TH 2025 | SPEED DATING @ TIME OUT MARKET | AGES 29-42
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Speed Dating @ Time Out Market - December 14th 2025
Ages: 29-42 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission – Ends 12/9 | $32.95
Regular Admission | $36.00
DECEMBER 20TH 2025 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 29-42
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - December 20th 2025
Ages: 29-42 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 12/15 | $34.95
Regular Admission | $38.00
DECEMBER 21ST 2025 | SPEED DATING @ TIME OUT MARKET | AGES 36-48
Speed Dating @ Time Out Market - December 21st 2025
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission – Ends 12/16 | $32.95
Regular Admission | $36.00
DECEMBER 27TH 2025 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET | AGES 24-36
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Time Out Market - December 27th 2025
Ages: 24-36 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 12/22 | $34.95
Regular Admission | $38.00
DECEMBER 28TH 2025 | SPEED DATING @ TIME OUT MARKET | AGES 36-48
Speed Dating @ Time Out Market - December 28th 2025
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission – Ends 12/23| $32.95
Regular Admission | $36.00
DECEMBER 31ST 2025 | SPEED DATING @ AC BOSTON DOWNTOWN | AGES 29-42 | NEW YEAR’S EVE BASH
New Year’s Eve Speed Dating @ AC Boston Downtown - December 31st 2025
Ages: 29-42 | 7PM
225 Albany St, Boston, MA 02118
Regular Admission | $38.00
JANUARY 3RD 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 29-42
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - January 3rd 2026
Ages: 29-42 | 5PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 12/29 | $34.95
Regular Admission | $38.00
JANUARY 4TH 2026 | SPEED DATING @ TIME OUT MARKET | AGES 36-48
Speed Dating @ Time Out Market - January 4th 2026
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission – Ends 12/30 | $32.95
Regular Admission | $36.00
JANUARY 8TH 2026 | SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 22-32
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Speed Dating @ Scholars American Bistro and Cocktail Lounge - January 8th 2026
Ages: 22-32 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 1/3 | $32.95
Regular Admission | $36.00
JANUARY 10TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET | AGES 24-36
Saturday Night Speed Dating @ Time Out Market - January 10th 2026
Ages: 24-36 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 1/5 | $34.95
Regular Admission | $38.00
JANUARY 11TH 2026 | SPEED DATING @ TIME OUT MARKET | AGES 29-42
Speed Dating @ Time Out Market - January 11th 2026
Ages: 29-42 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission – Ends 1/6 | $32.95
Regular Admission | $36.00
JANUARY 17TH 2026 | SATURDAY NIGHT SPEED DATING @ AC BOSTON DOWNTOWN | AGES 29-42
Saturday Night Speed Dating @ AC Boston Downtown - January 17th 2026
Ages: 29-42 | 7PM
225 Albany St, Boston, MA 02118
Early Bird Admission - Ends 1/12 | $34.95
Regular Admission | $38.00
JANUARY 18TH 2026 | SPEED DATING @ TIME OUT MARKET | AGES 36-48
Speed Dating @ Time Out Market - January 18th 2026
Ages: 36-48 | 6PM
401 Park Dr, Boston, MA 02215
Early Bird Admission – Ends 1/13 | $32.95
Regular Admission | $36.00
JANUARY 24TH 2026 | SATURDAY NIGHT SPEED DATING @ TIME OUT MARKET | AGES 24-36
Saturday Night Speed Dating @ Time Out Market - January 24th 2026
Ages: 24-36 | 7PM
401 Park Dr, Boston, MA 02215
Early Bird Admission - Ends 1/19 | $34.95
Regular Admission | $38.00
JANUARY 25TH 2026 | SPEED DATING @ AC BOSTON DOWNTOWN | AGES 36-48
Speed Dating @ AC Boston Downtown - January 25th 2026
Ages: 36-48 | 7PM
225 Albany St, Boston, MA 02118
Early Bird Admission – Ends 1/20 | $32.95
Regular Admission | $36.00
JANUARY 31ST 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 29-42
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - January 31st 2026
Ages: 29-42 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 1/26 | $34.95
Regular Admission | $38.00