The Five Dates You'll Go On in Back Bay

The Five Dates You'll Go On in Back Bay

“Let’s meet for drinks sometime.” It’s the death knell of any dating app conversation - a vague invitation that ultimately withers as each side volleys back with indecision. End the “I don’t care, you choose” attrition with our date ideas - uniquely tailored for all the matches you’ll meet in the Boston dating world! 

Boston may be The Hub, but Back Bay is its heart, teeming with art, cuisine, history and culture. This week, we’re exploring all the best date ideas in Back Bay, from breakfast foods and books to comedy, and even a library! (And where better to find someone to accompany you on these dates than at Boston YPA’s Single Mingle, coming up on September 25 at The Brahmin?)


The date: brunch with a bookish babe.

The play: Trident Booksellers & Cafe

A restaurant-meets-bookstore is the perfect date spot for a lover of literature. Browse the titles while you wait for a table, then gab about what you’ve been reading over brunch. Offerings range from hangover-helper grease to health-nut chia bowls and smoothies, so there’s a little something for every taste both on the menu and the shelves. (We recommend the Morning Monte Cristo, pictured above.) If there’ll be a second date, pick out books for each other to discuss next time you meet!


The date: a thrifty oenophile.

The play: Wine Tasting at the Charlesmark Hotel.

Returning from a two-year hiatus, the Charlesmark’s monthly wine tasting is one of Boston’s best kept secrets. For $25 each, you and your date will sample six wines, nosh on light bites (the meatballs and arancini are to die for!) and try two signature martini shots. Once the tasting is through, pop next door for dinner and a cocktail at Ora Trattorizza, the hotel’s brand-new restaurant with a tempting menu of Italian classics and comfort food. It’s the perfect way to “wine” down your Wednesday!


The date: loves to laugh.

The play: Comedy Night at McGreevy’s.

Twice weekly, this iconic Boylston Street pub is home to the city’s most up-and-coming comics that’ll have your guy or girl giggling! Get there early to take advantage of their nightly specials (50 cent wings on Mondays, $5 burgers on Tuesdays). Alums of the show have gone on to successful comedic careers -- who knows, you could be in the presence of the next big name in comedy! Check their Facebook page for more info.

Top of the Hub.jpg

The date: always open to sharing views.

The play: Top of the Hub.

You’ll feel on top of the world at this iconic spot! The vistas from the 52nd floor of the Prudential Tower are one of a kind. Snap some IG-worthy pictures, then try to see if you can spot your house from here. Then, enjoy a cocktail in the lounge, where live music amps up the ambiance every night of the week. Your Instagram post won’t be the only thing lighting up with hearts.


The date: a geography whiz.

The play: the Mapparium at the Mary Baker Eddy Library.

This glowing globe is a must-see for a cartography lover. Point out obscure countries, then stand on opposite sides and whisper sweet nothings to each other. After, take a stroll around the beautiful Christian Science Plaza. With its signature water features and reflecting pool, it’s one of the most romantic spots in Boston! (Pro tip: the library, along with other local cultural attractions, is free on October 14 for the annual Opening Our Doors celebration!)

National Coffee Day

National Coffee Day

The Weekend Guide: September 19th-22nd

The Weekend Guide: September 19th-22nd