"I don't care." The answer you've probably received (or given) time and time again in response to the question of what should we do tonight. Maybe she really doesn't care...I mean as long as you guys are together, right? Cute, but doesn't make for an easy planning process. Believe me, I know - I'm the queen of I don't cares.

So let's make it easy. Bypass the indecisive musings and have a plan already set in action for your next date. I've done the hard part for you and rounded up 21 places that I can almost guarantee to be a hit with your lady friend this winter. All you have to do is pick one and rack up those brownie points.

And TBH, if it involves food, booze, or anything with the word spa - you can't really go wrong.

via @eastcoastfeastcoast

Somewhere to indulge in insanely delicious food


Any one of these excitingly new restaurants // throughout Boston

Brownie points for taking her somewhere she hasn't been before.


Top of the Hub // 800 Boylston St

Brownie points for the view.


Eataly // 800 Boylston St

Brownie points for introducing her to heaven.


via @karlalondon

Somewhere where she can get her drink on


The Wine Bottega // 341 Hanover St

Brownie points for taking her on Friday for free wine tastings from 5-8pm.


Drink // 348 Congress St

Brownie points for helping her discover her new fave cocktail.


Brewery tour // throughout Boston (here are some of our favorite MA beers)

Brownie points for the interactive experience.


via @nianhu

Somewhere to satisfy her nagging sweet tooth


Any one of these dessert destinations // throughout Boston

Brownie points for picking the place that offers her favorite dessert.


Sugarfina // 800 Boylston St

Brownie points for the guaranteed sugar high.


Omni Parker House // 60 School St

Brownie points for exposing her to the OG Boston Cream Pie.


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Somewhere where she can let her inner child run free


Sacco's Bowl Haven // 45 Day St, Somerville

Brownie points for bowling AND insanely delicious pizza.


Boda Borg // 90 Pleasant St, Malden

Brownie points for probably the most unique date she's ever been on. (It's a real-world gaming environment called questing.)


Boston Winter // City Hall Plaza

Brownie points for taking her ice skating.


via @extrapetite

Somewhere that offers a true cultural experience


Museum of Science // 1 Science Park

Brownie points for the Astronomy After Hours.


Isabella Stewart Gardener Museum // 25 Evans Way

Brownie points for the beautiful midwinter tropics garden in the courtyard.


The Institute of Contemporary Art //  25 Harbor Shore Dr

Brownie points for taking her during one of the First Friday event series.


via @undefined

Somewhere that can keep her entertained


Coolidge Corner Theater // 290 Harvard St, Brookline

Brownie points for taking her to the movies in style.


The Paint Bar // 248 Newbury St

Brownie points for letting her laugh at your artwork.


Improv Asylum // 216 Hanover St

Brownie points for even more laughter.


via @agrl7

Somewhere she can get the pampering she deserves


The Spa at the Mandarin Oriental // 776 Boylston St

Brownie points for the crystal steam room.


Bella Santé // 38 Newbury St

Brownie points for couples massage.


Float // 515 Medford St, Somerville

Brownie points for taking her to the trendiest treatment out there.

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