12 Unique Date Ideas Boston Singles Need to Try

Couple on a great coffee date

Beantown, Titletown, The Hub, The Olde Towne… No matter what you call it, Boston has proven its diversity both in its nicknames and in the amount of things there are to do. Why settle for dinner and a movie? Shake things up with these great Boston date ideas!

The Boston dating scene is vibrant and varied – once you’ve met your match through us, be sure to check out one of our 12 favorite places in the city…

1: Improv Asylum

Skip the movies and go to a different kind of theater. Located in the basement of a CVS, Improv Asylum is the perfect place to bring a date when you’re wondering what to do in Boston for a night of fun and lots of laughs. The performers improvise around partially written skits, but they also take many cues from the audience and create a good mix of performance and interaction to keep everyone on their toes. Show your date your funny side, and don’t worry if you need something to boost your confidence—there’s also a fully stocked bar there to help you out.

2: Paint Nite

For those looking for creative Boston date ideas, Paint Nite offers the perfect opportunity to show off your artistic side. Each class can get packed up pretty quickly, but this provides a great reason to cozy up next to your date and feed off of each other’s creativity. Don’t worry if the thought of drawing anything beyond stick figures secretly terrifies you; the instructors make things easy for everyone. Oh, and also, did we mention that there’s a full bar here, as well?

3: Museums

If you’d prefer to look at art rather than create it, visit one of Boston’s many museums. The Institute of Contemporary Art is included in pretty much every list regarding what to do in Boston, and for good reason. Make sure you take advantage of the audio guide to get some context on the artwork. The Museum of Fine Arts is another notable museum, and it offers complimentary second visits within 10 days in case you feel like you might have missed anything. And if neither of those suits you, the Isabella Stewart Gardner Museum is filled with plants and tapestries along with the paintings.

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4: “Brunch Fiesta” at Masa

If brunch is known for being a couples thing, then the brunch fiesta at Masa just might be one of the most romantic things to do in Boston. You will be hard pressed to find a better deal anywhere in The Hub. With tasty food, excellent ambience, and attentive service, it’s a great place to come for other meals, as well. Just be warned, if you do plan to go to their brunch fiesta, it can get quite crowded, so call ahead and make a reservation first!

5: Cambridge Center Roof Garden

Why go to a regular park on the ground floor when you have the option of going to a rooftop park? This is one of the more unique date ideas in Boston, since you won’t find it in any other city. Pack a meal for your date and use one of the park’s picnic tables or sit on the gorgeous grass and enjoy the views of the city. They also have various activities like yoga sessions and even a ping pong table to keep things active and fun, but it’s also a great place to just relax and escape the general hubbub of the city without actually having to leave it.

Find your perfect date spot using the interactive map below!

6: Free Wine Tasting at Central Bottle

Yes, you read that right. Central Bottle offers free wine tastings four times a week, although sometimes they like to mix it up with a cheese tasting or beer tasting. Check out their website to see what they’re offering during the week you’d like to visit. This event is preferable to meeting at a regular bar for many reasons; one, because it’s free, of course, but also because the activity of wine tasting will give you and your date plenty of things to talk about with each other. There’s a reason wine is commonly associated with romance, as you will find out with one of the more romantic things to do in Boston at Central Bottle.

7: Top of the Hub

This isn’t just a tourist destination! It’s also a wonderful choice for date ideas in Boston. Touted as “Boston’s most romantic dining experience,” you won’t be hearing any claims to the contrary from us. Located 52 floors above the Back Bay, Top of the Hub has quite possibly the best views of the city you can get short of taking a helicopter ride. Their award-winning cuisine will satisfy any appetites you’re likely to bring, and their impeccable service will leave you feeling like you’re a well-loved regular. If you dine early, make sure to stick around for the sunset and live music being played in the lounge.

8: The Mapparium

Who hasn’t ever dreamed of stepping into a gigantic globe? The Mapparium at The Mary Baker Eddy Library is a three-story-tall globe made of stained glass. Visitors walk through the middle of it on a 30-foot-long bridge. It’s a very short tour (about 20 minutes), so plan to get a bite or a drink afterwards to talk more with your date. Keep in mind, they don’t allow photos in here, so leave your smartphone in your pocket (where it should remain during the date), but you most likely won’t mind once you hear the whispers that travel around the world. No spoilers! You’ll see what we mean when you go.

9: The Skywalk Observatory

If you’d rather skip the restaurant idea from tip number seven on this list of Boston date ideas but still want to get the magnificent view, The Skywalk Observatory is the perfect place for you. Offering 360-degree panoramic views of Boston from 50 floors up, The Skywalk Observatory is a must-see for visitors and locals alike. Make sure to request the audio guide from the front desk for an informative history presentation of the city. It will give great talking points for you and your date to discuss amongst each other. Try to go slightly before sunset in order to get views of the city during the day and night.

10: Paddle Boston

Get in touch with your physical, aquatic side with one of the more unique date ideas Boston has to offer. Paddle Boston allows you to kayak on the Charles River from four locations and offers two-hour tours with special instructions in case you don’t have any prior experience using a kayak. Their Kendall Square location is conveniently located next to plenty of restaurants to choose from when you finish, giving you and your date the perfect opportunity to unwind and toast each other to a wonderful new memory the both of you will be sure to cherish for a long time to come.

11: Speakeasy Bars

Explore the “hidden” side of Boston by taking your date to a speakeasy bar. The entrances may be difficult to find and might seem a bit sketchy at first, but you will definitely be rewarded with a great experience unrivaled by most bars that choose to remain in plain sight. Backbar’s entrance lies down an alleyway in Union Square that may or may not resemble where crime victims like to congregate, but the bar itself will make you willing to traverse that path again and again. And somewhere in Davis Square, Saloon’s rustic charm and tasty cocktails come together to create an intimate environment for you and your date.

12: The Algiers Coffee House

Getting coffee is the cliché first date idea for good reason. It is usually a calm environment with few distractions, putting the emphasis on talking and getting to know one another. But that doesn’t mean you have to settle for the uniformity of one of the big coffee chains. Setting is important, and The Algiers Coffee House will inject some fantastic, much-appreciated ambience into any first date, almost making you feel as if you’ve been transported into an old Moroccan café. Opt to rendezvous with your date here in order to get a fresh take on what would otherwise be another of the standard Boston date ideas.

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