Walk along the Esplanade
One of the most beautiful spots for a stroll in the entire northeast, the Esplanade offers a gorgeous view of the Charles River with downtown Boston as a backdrop. If you can’t make this romantic, there may be no hope for you.
Oyster happy hour
It is still illegal for bars to offer happy hour drinks in the state of Massachusetts (thanks a lot, Puritans), so bar and restaurant owners have circumvented this law by advertising outrageously cheap oysters and other dining options. If you and your date happen to order a few cheap drinks along with your meal, well, that is your choice.
Boston food truck culture has experienced a boom in the last decade, both in numbers and variety. For a cheap and delicious dining option, grab some grub from one of the city’s countless ethnic food trucks and take it to the nearest park.
Free museum nights
Trick your date into thinking you are smart and cultured by planning a fun—and free—evening at one of the many art and historical museums in Boston. With well over 80 cultural institutions in the city, there is something for just about every interest.
Free music festivals
At the time of this writing, the author is less than six hours away from seeing George Clinton & Parliament Funkadelic play for free at a local street festival. He is bringing a Tinder date with him.
Picnic in the park
There are several parks in Boston with enough greenery to offer a quick escape from the hustle and bustle of the city. Tell your date you are the “outdoorsy type,” grab some cheap food from a taco truck and find a nice spot in the shade.
Beer and wine tastings
Another clever way to look cultured when really you are just broke is to join a wine tasting. There is no shortage of wine and spirits shops in Boston, many of which offer special tasting events and promotions for little or no money. If you and your date are more into beer, take a tour of one of Boston’s breweries and enjoy the free beer at the end.
Free outdoor movies
Remember that walk along the Charles River (see above)? If you are really clever, you can time it to arrive at the Hatch Memorial Shell on one of the free movie nights hosted there in the summertime. Last month they showed The Jungle Book, arguably the greatest film of all time.
Lawn on D
Another great outdoor spot for movies, art galleries, and exhibitions, Lawn on D is one of the most unique (and highly Instagrammed) event spaces in Boston. It also happens to be located on the waterfront, which has an evening view that makes everything you do and say seem romantic by default.
Ice skating at the Charles Hotel
When it’s too cold for outdoor activities but you still want to feel like you’re in an ’80s movie, the Charles Hotel opens its rink to the public for only $5 per person. At that price, you can afford to tip the DJ a few bucks to play “Baby, It’s Cold Outside” on your way out.