Looking for a date idea that's fun and not totally cliche? Check out a few of these suggestions, thanks to Thrillist:
Cocktails and oysters at the Hotel Commonwealth | Kenmore Square
"Surprise your date with a night in Kenmore Square that doesn’t revolve around an overcrowded Sox bar. Kick your night off at The Hawthorne with a classic cocktail or one of the house creations like the Esperanto (crema de mezcal, La Ciggarrera manzanilla, Carpano Antica, and orange bitters). Once you’ve worked up an appetite, head across Hotel Commonwealth’s lobby into Island Creek Oyster Bar for some of the ocean’s best bivalves (oysters average $3/each). Between the perfectly concocted cocktails and aphrodisiac power of the oysters, you two will be primed to plan your second encounter. If you don’t want the night to end, tack on a visit to the Boston University Observatory, where you can see the beautiful Boston skyline with the telescopes on hand."
Authentic Italian and improv comedy | North End
"When going out for dinner and drinks at an authentic Italian restaurant in the North End, there're Monica's, Prezza, and dozens of other trattorias worth hitting. Then get ready for a pee-your-pants funny improv show at the Improv Asylum. Protip: put your name on the waitlist at Neptune Oyster (since it typically has a two-hour wait!), then watch the comedy show at the Improv Asylum while waiting for the restaurant to call your cell when a table frees up -- and then head over there when the show is over."
Walk the Esplanade to Harvard Square | Back Bay to Harvard Square
"For a date that's easy on your wallet, go for a stroll along the Esplanade and head towards Harvard Square. There are often different festivals going on in the Esplanade around the holidays, and it also offers one of the best views of fall foliage in Boston. Once you've finished the three-mile walk from Back Bay, reward yourselves with a drink, either downstairs at Russell House Tavern or in the beer garden at Charlie's Kitchen."
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