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 matchmaking in this city.
Planning something special for Valentine’s Day? Discover our Boston Valentine’s speed dating events — a relaxed, in-person way to meet someone new this February.
JANUARY 31ST 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 29-42
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
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
FEBRUARY 1ST 2026 | SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 29-42
Speed Dating @ Scholars American Bistro and Cocktail Lounge - February 1st 2026
Ages: 29-42 | 6PM
25 School St, Boston, MA 02108
Early Bird Admission – Ends 1/27 | $32.95
Regular Admission | $36.00
FEBRUARY 7TH 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 24-36
*MEN SOLD OUT - Gentlemen, Wait List tickets available for purchase.*
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - February 7th 2026
Ages: 24-36 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 2/2 | $34.95
Regular Admission | $38.00
FEBRUARY 8TH 2026 | SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 36-48
Speed Dating @ Scholars American Bistro and Cocktail Lounge - February 8th 2026
Ages: 36-48 | 6PM
25 School St, Boston, MA 02108
Early Bird Admission – Ends 2/3 | $32.95
Regular Admission | $36.00
FEBRUARY 14TH 2026 | 'BE MY VALENTINE BASH' @ AC BOSTON DOWNTOWN | AGES 29-42
'Be My Valentine Bash!'
Speed Dating @ AC Boston Downtown - February 14th 2026
Ages: 29-42 | 5PM
225 Albany St, Boston, MA 02118
Regular Admission | $39.00
FEBRUARY 15TH 2026 | SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 29-42
Speed Dating @ Scholars American Bistro and Cocktail Lounge - February 15th 2026
Ages: 29-42 | 6PM
25 School St, Boston, MA 02108
Early Bird Admission – Ends 1/27 | $32.95
Regular Admission | $36.00
FEBRUARY 21ST 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 29-42
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - February 21st 2026
Ages: 29-42 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 1/26 | $34.95
Regular Admission | $38.00
FEBRUARY 22ND 2026 | SPEED DATING @ AC BOSTON DOWNTOWN | AGES 36-48
Speed Dating @ AC Boston Downtown - February 22nd 2026
Ages: 36-48 | 7PM
225 Albany St, Boston, MA 02118
Early Bird Admission – Ends 2/17 | $32.95
Regular Admission | $36.00
FEBRUARY 28TH 2026 | SATURDAY NIGHT SPEED DATING @ SCHOLARS AMERICAN BISTRO AND COCKTAIL LOUNGE | AGES 24-36
Saturday Night Speed Dating @ Scholars American Bistro and Cocktail Lounge - February 28th 2026
Ages: 24-36 | 7PM
25 School St, Boston, MA 02108
Early Bird Admission - Ends 2/23 | $34.95
Regular Admission | $38.00
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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