It's A Date - Boston’s Hottest Comedy Dating Show at Castle Island Brewing

Wed Aug 13 2025 at 08:00 pm to 09:30 pm UTC-04:00

Castle Island Brewing - South Boston | Boston

It's A Date Boston
Publisher/HostIt's A Date Boston
It's A Date -  Boston\u2019s Hottest Comedy Dating Show at Castle Island Brewing
Advertisement
Four volunteering singles go on a blind date, blindfolded. Get ready for a hilarious evening of romance and chaos!
About this Event

DOOR: 7:30PM

SHOW: 8PM - 9:30PM


"It's A Date" is New England's hottest comedy dating show where four singles take the stage blindfolded and let their charms do the seducing, while the audience throws in deep and spicy questions. Get ready for a night where laughter, mystery, and unexpected sparks collide.


Here's how it works:

Before the show kicks off, attendees are invited to a quick mingle session, perfect for meeting new people or enjoying some laughs before the main event.

Once the show begins, four singles, who apply ahead of time at the link HERE, take the stage blindfolded for a hilarious and unpredictable blind date, relying on smooth talk and quick wit to spark a connection. The audience fuels the heat by asking bold and flirty questions that nudge the four contestants to reveal their true selves.

At the end of the night, the crowd votes to pick out one perfect match couple, who will win a second date outside of the show, planned and paid for by "It's A Date".

Whether it’s steamy, hilarious, awkward or unexpectedly wholesome, "It's A Date" guarantees a night of entertainment where romance and laughter ignite. Anything can happen—and who knows, love just might be in the air.


LEGAL DISCLOSURE*By agreeing to purchase a ticket and/or attend the show, you hereby agree to It’s A Date, LLC’s (“It’s A Date”) appearance release and participation agreement. You will be granting It's A Date and all its subsidiaries permission to take motion and still pictures, record your voice and any sound made by you and to use the footage and materials in the development, production, distribution, advertising, and promotions of the show without any monetary compensation to you in perpetuity.

Advertisement

Event Venue & Nearby Stays

Castle Island Brewing - South Boston, 10 Old Colony Avenue, Boston, United States

Tickets

USD 17.85 to USD 30.65

Sharing is Caring:

More Events in Boston

The Blob (1988) in 35mm (Free Screening at the Greenway)
Wed, 13 Aug at 08:00 pm The Blob (1988) in 35mm (Free Screening at the Greenway)

Rose Kennedy Greenway

Beres Hammond at Wilbur Theatre
Wed, 13 Aug at 08:00 pm Beres Hammond at Wilbur Theatre

Wilbur Theatre

Watch Wednesday: The Barbie Movie
Wed, 13 Aug at 09:00 pm Watch Wednesday: The Barbie Movie

The Anchor

The Wiz - Boston
Wed, 13 Aug at 11:00 pm The Wiz - Boston

Citizens Bank Opera House

Parking The Wiz - Boston
Wed, 13 Aug at 11:00 pm Parking The Wiz - Boston

Citizens Bank Opera House

Boston Wine Tasting
Thu, 14 Aug at 12:00 am Boston Wine Tasting

The Eliot Hotel, Boston

Boston - Breakfast Club
Thu, 14 Aug at 08:00 am Boston - Breakfast Club

HGA

Summer Preschool Programs at the Waterworks: Ice Painting
Thu, 14 Aug at 10:00 am Summer Preschool Programs at the Waterworks: Ice Painting

Metropolitan Waterworks Museum

Health City: A Resource Fair at The Greenway
Thu, 14 Aug at 11:00 am Health City: A Resource Fair at The Greenway

Rose Kennedy Greenway @ Dewey Square

Around the World Storytime
Thu, 14 Aug at 11:30 am Around the World Storytime

Boston Public Library

Boston is Happening!

Never miss your favorite happenings again!

Explore Boston Events