5 Hilariously Awesome Date Ideas

January 15, 2020

Charlie Chaplin once said, “A day without laughter is a day wasted.”

We’d like to revise that to say that a date without laughter is indeed a date wasted. But what if you and your date aren’t in the mood for a good ol’ rom com? You, my friends, are in luck.

There are a ton of great live comedy shows near you! And they’ll be sure to leave you both having a great time. Below, we’ve handpicked some of the best.

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    Sunset Sail

    (28)
    The maritime world of Boston has many great stories to offer, and on this classic sail through the Boston Harbor, as the Sun dips below the horizon, you'll get to see and hear it all. Experience the sights of the Boston Fish Pier, The Moakley Federal Courthouse at Fan Pier, Castle Island, the Donald McKay monument, the Charleston Navy Yard, and much more, on a sail aboard the Adirondack III, a classic 80 foot pilot schooner. Experience Boston like never before, on a schooner, a drink in hand, and a knowledgeable captain and crew to ask about all the stories behind some of Boston's most unforgettable sights.
    Sunset Sail

    60 Rowes Wharf, Boston

    • Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
    • Experience a beautiful Boston Harbor sunset on the water
    • Ask your knowledgeable staff and crew anything you'd like to know about the sights
    • Enjoy the ride, see the sights and have a drink onboard
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    28 positive reviews
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    Wine, Cheese, and The Pursuit of Happiness

    ...Endowed with certain inalienable rights, that among these, are wine, cheese, and the pursuit of happiness. In this tasty class, pursue your own happiness through delicious wine and cheese pairings: creamy brie, crunched aged gouda, and tangy blue cheeses. Stomach growling yet? After sampling wines and cheeses, you will sit down and enjoy a delicious dinner, complete with food and wine pairings. Discover the spectrum of wine and cheese and other strategies for making great matches, during this fun, one-of-a-kind class.
    Wine, Cheese, and The Pursuit of Happiness

    2 Merchant Street, Sharron

    • Pair a collection of wines with their perfect cheese counterparts
    • Enjoy a delicious dinner, and a wine accompaniment with each dish
    • Distinguish the spectrums of wine and cheese, and learn strategies for making perfect pairings in the future
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    Pizza and Historic Tavern Tour

    (24)
    "One if by land, two if by sea." Add it up, and that's how many slices of pizza you'll be eating on this tour. If you don't take this for yourself, take it for Paul Revere. Combining a stroll through Boston's oldest neighborhoods with a ferry ride across Boston harbor, you'll enjoy three slices from the best pizza in the city, while also visiting two of Boston's most historic taverns. As you taste your way through the city, indulge in a drink or two at "Headquarters of the Revolution" and even stop by a tavern once visited by Mr. George Washington. That's 375 years of tavern history! Get ready to eat, drink, and be merry.
    Pizza and Historic Tavern Tour

    Hanover St & Cross St, Boston

    • Explore Boston's oldest neighborhoods and enjoy a ferry ride across Boston harbor
    • Taste three slices of Boston's very best pizza
    • Visit two of the city's most historic taverns, including Three Cranes Tavern and a bar once visited by George Washington
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    24 positive reviews
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    Stone Setting and Ring Workshop

    (14)
    Rings can be great fashion statements, but they kind of lose their appeal when everyone else has the same one you do. Why not learn to make your own custom rings? In this jewelry making class, take a quick spin through several jewelry making techniques, including measuring, cutting, customizing, soldering, shaping and buffing. After learning the basics, create your own silver ring with a bezel set stone, perfect to either give to someone special or rock on your own!
    Stone Setting and Ring Workshop

    24 Porter St, Jamaica Plain

    • Explore the basics of ring making in a fun and educational introductory workshop
    • Learn basic crafting techniques including measuring, cutting, and soldering
    • Practice bezel setting stones to further customize your creations
    • Enjoy a warm setting that encourages creativity
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    14 positive reviews
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    The Sip of Boston Brew Tour

    (26)
    Boston nightlife plus the Boston brews equals the best night you can have in Beantown. Begin your night on the town with a quick bar crawl to get ya in the mood. On this Brew Pub Crawl, you'll taste twenty different beers, enjoy an artisan dinner at Area Four, and you'll receive round-trip transportation throughout the evening. Taste the array of stouts, pilsners, and ales that call Boston home. You'll visit the city's top breweries in its after hours. Are you ready yet? Because it's time to taste some beer!
    The Sip of Boston Brew Tour

    143 Charles St, Boston

    • Taste twenty different beers, including various stouts, pilsners, and ales, on this Boston brew pub crawl
    • Enjoy an artisan dinner at Area Four
    • Travel with round'trip transportation throughout your entire evening
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    26 positive reviews
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    Make a Ring

    (14)
    Rings can be great fashion statements, but they kind of lose their appeal when everyone else has the same one you do. Why not learn to create your own custom rings in this jewelry making class! Take a quick spin through several jewelry making techniques, including measuring, cutting, soldering, shaping and buffing metal under instruction from master craftsmen. After learning the basics of fashioning a ring from silver, create your own and customize it however you'd like. Leave with a beautiful accessory to either give to someone special or rock on your own to show off your new skill!
    Make a Ring

    24 Porter St, Jamaica Plain

    • Explore the basics of ring making in an introductory workshop
    • Learn basic techniques including measuring, cutting, and soldering
    • Express individuality customizing your your ring's design
    • Leave with a beautifully hand-crafted souvenir to either keep or give as a gift
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    14 positive reviews
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