You’ve finally asked out that special someone in your economics class, and they said yes! Now you just have to find something to do with them. Try getting out of the “Harvard bubble” and doing something new!
Go to dinner in the North End
A Boston classic, dinner in the North end will never disappoint. If you’ve been before, try a new restaurant and if you have never been, pick the first place you see and you’ll love it! Leave room for desert, but don’t order at the restaurant. Try Mike’s or Modern Pastry, or my personal favorite: Maria’s Pastry for a delicious cannoli or sfogliatelle.
What to wear: Nothing too fancy, just a nice shirt will do.
Get dressed up and go check out a Broadway show in Boston’s Theatre District or for the more musically inclined, go to a concert at the Boston Symphony Orchestra. While you’re there admire the architecture of the First Church of Christ and gaze into the reflecting pool (it’s romantic). If you don’t want a fancy date, get some laughs in at the Improv Asylum over in the North End. Careful though, they might call you up on stage to act in front of everyone!
What to wear: If it’s a nice show, you’ll need a tie. Try this one.
Do you both enjoy shopping? Take a stroll down Newbury and Boylston Streets and check out all of the shops. If you get hungry, there are plenty of restaurants and bars along the way. If you like burgers and nachos, you have to try Whiskey’s, located right across the street from the Prudential Center.
What to wear: anything you want!
More Places to Eat
The Union Oyster House is a must-go-to restaurant in Boston if you want to get some of the best seafood you’ll ever eat. Be sure to try the oysters on the half shell (they’re raw!) and wash it down with a Sam Adams you can only get at the Union Oyster House. This restaurant is the oldest in the country, and the wait can be long so make sure to make reservations.
Tired of rolling into Sunday brunch in your sweats? Want something a little fancier with better views than the hung-over kids next to you? Make some reservations at Top of the Hub for a four course brunch with the best views around. Plus if you tell them it’s your birthday or anniversary, they’ll go above and beyond with your dessert!
What to wear: put on something nice, if it’s cold try this sweatshirt.
If you’re looking for a romantic, but not expensive date, take a stroll through Boston Common and the Public Garden. If it’s warm out, take a ride on the famous swan boats, one of the more romantic aspects of the garden. As you walk around, try to find the statues of the ducklings (and maybe read the book before you go) so you can charm your date with your knowledge about Boston. If it’s winter, you can go ice skating on the frog pond. Don’t worry if you can’t skate, falling is cute!
What to wear: Boston can get windy, you might want a sweatshirt!
Feeling nautical? Spend the evening on board the Odyssey or Spirit of Boston. This date will include fine dining, unparalleled waterfront views of Boston, and even some dancing! Bring along another couple for a great double date!
What to wear: stay classy with a Harvard bow tie!
For something really different, rent a zip car and get out of the city entirely! There are lots of apple orchards just outside the city where you can pick your own apples and sample the cider and cider donuts!
If you’re feeling really adventurous and outdoorsy, drive all the way out to Western Mass during the fall and take in some of the best foliage in New England. Hike around the Quabbin reservoir or in the Berkshires for a romantic mini-getaway.
What to wear: in the fall, stay warm and fashionable with the classic H Sweater.
In the winter, hit the slopes at one of the local ski resorts. Whether you’re a beginner or expert, skiing and snowboarding will get your adrenaline pumping! Go as a date for two or a big group of friends and escape the dreary city during the winter.
What to wear: bundle up, winters are cold in New England!
If you’re around during the summer, there’s no place better than Cape Cod for a day trip to the beach. You can even catch a bus or train from South Station. Find a friend with a place down on the cape and take off for the day to take in some rays!
What to wear: sun’s out guns out.
If you live near Boston, you went to the aquarium a dozen times for elementary school field trips, but who doesn’t love seeing the fish in the giant center tank? Take your date here and definitely check out the sea lion show outside!
What to wear: anything goes at the aquarium, but don’t try to go swimming!
Boston has the best sports teams ever. It’s a fact. Go to the garden and cheer on the Bruins or Celtics (or the team from your home city, which will lose to Boston). And nothing says “we’re on a date” better than a picture together at Fenway Park. Catch a Sox game at the oldest and best park in the country, and don’t forget the Fenway Franks!
What to wear: Ice rinks and Fenway Park will get cold so come prepared with a jacket.
Summer on the Charles – kayak, sailing, walk
For the active couples during the summer, try renting kayaks or sailboats and taking them out on the Charles. If water sports aren’t your thing, summer evenings are the perfect time for a romantic walk by the river
What to wear: this depends on the activity, but make sure to bring water and stay hydrated.