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The Simmons Voice

The Student News Site of Simmons University

The Simmons Voice

The Student News Site of Simmons University

The Simmons Voice

Best Date Night Spots in Boston to spice up your Valentine’s Day <3

Have no fear over-zealous-lesbians and 6-on-a-good-day boyfriends!

Valentine’s Day, like most holidays created by Hallmark and Lindt to sell more cards and chocolate (allegedly), can strain a relationship to create the perfect date night. So have no fear over-zealous-lesbians and 6-on-a-good-day boyfriends; Boston Cupid is here to give you the top 5 best date night places in downtown Beantown!

Number 1: Boston City Hall:

Boston City Hall is the perfect date night spot to get you and your partner’s night going! Just take the Green line to Government Center (make sure it’s even running first…), and the ugliest building in the world welcomes you to a Valentine’s to remember. You can even find your city councilor and encourage them to fix the MBTA!

(Photo from Wikipedia)

Number Two: Downtown Clowning Around!

Canadian art exhibit Winteractive takes place in downtown Boston, but don’t let those damn socialists scare you, this is a truly memorable experience, as long as you are not part of the 53% of adults with Coulrophobia. You can find Nagg & Nell – yes, those are really their names – at 533 Washington St, Boston, MA. How many times in your life can you say you saw two giant inflated clowns bouncing around a Boston alley? Actually, don’t answer that.

(Photo Courtesy of Downtown Boston BID)

Number Three: Tavern in the Square (TITS) – South Station

Our next date night spot is Tavern in the Square in Boston’s glorious South Station. TITS, as it is called (also a nickname I’ve been given), is an excellent spot for $7 clam chowder (with artificial clams), $9 guacamole (made by the whitest person in Boston), and $6.50 on an alcoholic seltzer (that you could’ve stolen from your roommate for free). 

You can people-watch in the second-busiest New England Station from lost tourists who can’t read signs to a lone pigeon that has found his way inside and made a home among the Cabot Cheese posters. He performs under the stage name Rocky and sings covers of 90s hits to buy his next meal, dreaming that one day, he’ll be on Broadway in New York City. You can find him performing on Friday nights in-between TITS and Dunkin Donuts. Known as the Patti Lupone of Boston, Rocky is a young up-and-coming star you want to meet so you can say you knew him when he was a fledgling. 

Rocky singing his favorite song,”My Heart Will Go On,” by Céline Dion. (Lily Boland)

Number Four: Longwood Galleria

Every Simmons student knows that the Longwood Galleria is the number one place to hang out on a Friday night. A mere walk from campus, this food court has everything to make a Simmons Shark feel safe in their home away from home. From the smell of greasy fried food to the mice and rats scrounging for dinner, the vibes could not be more like Bartol Hall. Plus, you have a much wider range of options, and you won’t get death stares when bringing your boyfriend over! The Longwood Galleria is a classic date night spot for a quick and easy date night for your quick and easy date. 

Boston is a hot spot for date nights and weekend adventures, and this is just a highlight of what the city has to offer. Boston Cupid hopes these Boston date night spots help you plan the perfect Valentine’s Day date night or even your next Hinge date (8th time’s the charm!).

Ratholomew and Ratthew on their first date. (Lily Boland)
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About the Contributor
Lily Boland
Lily Boland, Graphics Editor
Lily Boland (2027, she/her) is majoring in Arts Administration and Communications on the Digital Communications and Design track respectively. She is a member of the Honors program and the Sidelines Magazine team. Outside of student-driven media, she enjoys solving NYT crossword puzzles, exploring museums, and grabbing a cannoli with friends in the North End.

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