The Five Dates You'll Go On in Beacon Hill, West End, & North End

“Let’s meet for drinks sometime.” It’s the death knell of any dating app conversation. That vague invitation 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! This week, we’re exploring my home neighborhood and the best spots to set a perfect scene for your first date.

The date: a busy staffer for a state senator.

The play: 21st Amendment.

Your prospective paramour only has a few minutes for a beer and a bite before she has to head back to the State House to run an important Senate meeting. Suggest this spot, just outside the shadow of the golden dome. You can share an app (we recommend the slider plate — a perfectly splittable mini-meal) and make a fine first impression before she has to go take minutes for Senator Whatshisface.

Second date? Keep the prohibition theme going with a game of pool and cocktails, a block down the hill at Carrie Nation.

The date: a red-blooded Italian who loves his red sauce.

The play: Tony & Elaine’s.

Homestyle Italian food and 1970s throwback decor and music? That’s amore! Prolific restaurateur Nick Frattaroli took inspiration from his parents’ roots in his newest venture. The menu is stacked with classic dishes that’ll satisfy any Paisan looking for gravy like Grandma’s. Walk off the inevitable food coma with a stroll around the waterfront - it’s a mile to Modern Pastry if you take the long way around.

Second date? If you loved T&E, try diversifying cuisines at one of Frattaroli’s other local joints: Ward 8, North Square Oyster Bar/Ciao Bella, or Bodega Canal.

The date: a fan of architecture and history.

The play: The Liberty Hotel.

You may not guess this at first glance, but this chic boutique hotel and hot spot was once a prison! This building which once housed Boston’s most nefarious criminals is now home to some great local hot spots. Start with drinks in the lobby, where you can admire the panopticon-style cupola, and enjoy supper at Scampo. Finish off with a nightcap at Alibi and spot the celebrity mug shots adorning the wall.

Second date? Continue the tour of historic hotels at the Omni Parker House - just watch out for ghosts.

The date: a self-professed beer geek.

The play: Night Shift Taproom on Lovejoy Wharf.

Night Shift is quickly becoming one of Boston’s most recognizable local beer brands, and their new outpost — which just opened in Spring 2019 — is a huge step for the Everett-based brewery. Hop on over to the taproom and share some samples with your date; there’s a little something for every taste. Complement your suds with a selection of small plates like street corn, deviled eggs, chicharrones and rotating house popcorn. 

Second date? Take a walking tour of the city’s beer gardens: start with the Patios at City Hall, then Trillium’s Garden on the Greenway, and finish at Cisco in the Seaport.

The date: a longtime local who’s sick of tourist traps.

The play: Parla.

When you’ve been on the block for a while, every joint on Hanover Street starts to look the same. Except Parla. The moody, speakeasy vibe instantly sets this spot apart from its neighbors. The food is fine — a great bolognese isn’t exactly rocket science — but come for the cocktails, detailed in a multi-page menu wedged in an old sketchbook (doodling encouraged). If you’re a D&D fan, ask to roll the dice and try one of their 20 secret menu items. Your date may be inspired to talk nerdy to you.

Second date? Go back to Parla for another shot at the dice and another excellent cocktail, of course!

Stay tuned for next week, when we’ll be coming back at you with five all-new date ideas! Until then, have fun and happy dating!