Date Night Spots in Boston… and What To Order


When you’ve been single for a few years, you tend to be that person. You know, the one that your friends always want to set up. The one they turn to for advice when they themselves are entering the dating world. The one they cut off after too many glasses of sangria at a wedding. The one they assume spend every Friday night out at a hot new spot, when in reality you’re at home doing laundry and Facetime-ing with your parents. That’s me!

I’ve been lucky to have gone out with some pretty awesome guys, and I have had my share of funny dating stories: going out on a date with caramel stuck in my hair, getting asked out by a random/hot/young stranger while eating a kale salad, going out with someone who is allergic to chocolate (obviously that did not work out), or someone who looked like Ben Affleck (from the nose down), and another guy who looked like Jeremy Renner WITH GLASSES (oh yes).

So I think by now, with all these years of dating experience, my love for restaurants, and my innate obsession with making lists, I can give you some semi-professional-ish advice… on The Best Date Night Spots in Boston, and What To Order when you’re there.

Here are five of my favorite date spots, for different dating scenarios, and my suggestions on what to get:

horchata painted burro painted burro crab cake benedict

Brunch: The Painted Burro, Somerville

Order: iced coffee horchata or michelada + crab cake benedict

I love The Painted Burro for brunch. It’s bright and colorful, you have the option to drink margaritas and many different kinds of tequila, and you get free nachos and salsa (even for brunch). This combination is sure to put you and your date in a good mood. Order the iced coffee horchata (an iced Mexican drink made with ground almonds, rice, vanilla, and cinammon – transformed into a morning beverage with coffee) and your date is already off to a sweet start! Or you might enjoy the michelada more (a Mexican cocktail made with beer, lime juice, hot sauce, and other seasonings) if you’re the kinda gal or guy who likes alcohol early in the day. And I suggest the crab cake benedict because crab cake. Benedict.

The Painted Burro on Urbanspoon


Fancy or Special Occasion: O Ya, Leather District/Waterfront

Order: foie gras nigiri

O Ya is the best Japanese restaurant in town (and also the most expensive). I had my most extravagant meal there a few years ago and loved it. After going to Japan earlier this year, I have newfound respect for sushi (it really is like a work of art) and the food at O Ya is pretty impeccable (and did I mention expensive?) If you’re into sushi, too, then you probably already have your favorites, which you should order. But may I suggest the foie gras nigiri? It comes with a balsamic chocolate kabayaki, claudio corallo raisin cocoa pulp, and a sip of aged sake. So really, you get a good deal for ordering this because you also get sake.

O Ya on Urbanspoon

craigie burger

Foodie Date: Craigie on Main, Central Square

Order: the burger (only available at the bar)

I know a lot of people hate on the word “foodie” but Craigie on Main is a great spot for foodies. The food is local, seasonal, organic, farm-to-table, nose-to-tail eating. It’s a little bit fancy, a little bit country. I’ve been there for brunch, bar snacks, dinner, and while I liked everything I’ve had, my top choice is the burger (and after that, the crispy pig tails). The iconic burger is definitely one of the best in the city. Salty, juicy, and bursting with umami flavors; the patty contains different cuts of beef, bone marrow, and dehydrated miso. I also like the tasting menus at Craigie, and the Chef’s Whim on Sundays (a 6-course surprise menu for $57) is a fun way to try special dishes that may not be on the regular menu.

Craigie On Main on Urbanspoon

mexican cheetos lulus

Fun: Lulu’s Allston, Allston

Order: Mexican Cheetos

It’s fun! It’s kitschy! It’s in Allston! Maybe the exclamation points aren’t enough to make you head over to Allston but these Mexican cheetos with hot salsa should. Who doesnt’t like Cheetos? Lulu’s Allston is a good place for a fun date. The new bistro serves casual comfort food – like you’re eating “drunk food,” says The Boston Globe, and the menu really is filled with stuff that’s perfect for curing hangovers. The bar offers over 50 beers, cocktails (like the sangria pictured above), and other beertails (which is exactly what you think it is) so if you need liquid courage (or beer goggles), you’ll be all set.

Lulu's Allston on Urbanspoon

harvest taza cremeux

Romantic: Harvest, Harvard Square

Order: Taza Chocolate Cremeux

A date night round-up wouldn’t be complete without a nice place with a swoon-worthy chocolate dessert. Harvest is perfect for a romantic night out. The place feels very refined, but not at all stuffy. To get there, you have to walk through a charming little walkway in Harvard Square, and if the weather is good, you can sit outside at the lovely patio. You can’t go wrong with the classic American cuisine, and make sure you save room for dessert. The best is the Taza Chocolate Cremeux – intensely fudgy, with a thick caramel filling, served with crunchy granola, creamy mascarpone, and flakes of sea salt. Food may be the way to a man’s heart, and I think chocolate is the way’s to a woman’s, but both genders will agree on this sexy dessert. Share this with your date!

Harvest on Urbanspoon

If you see me at any of these spots on a date, please remind me that I shouldn’t order tequila shots (at least not on the first date). What’s your favorite date spot?  


23 Responses to “Date Night Spots in Boston… and What To Order”

  1. #
    dan posted August 7, 2014 at 9:20 am

    WAIT you play life coach to OTHER PEOPLE TOO???? waaaa I thought I was the only one!

  2. #
    Daisy posted August 7, 2014 at 9:36 am

    this is awesome!! and I’m happy to say I’ve now had that chocolate dessert ;)

    • #
      Bianca Garcia posted August 7, 2014 at 9:45 am

      That chocolate cake + vin santo = yum!

  3. #
    Melanie @ Bon Appet'Eat posted August 7, 2014 at 12:11 pm

    Great tips Bianca, thanks. Boston is on my bucket list :)

    • #
      Bianca Garcia posted August 7, 2014 at 12:59 pm

      Yes come to Boston! We’ll go on a date :)

  4. #
    Christina Orso posted August 7, 2014 at 2:32 pm

    hahah! no tequila shots on the first date! love that. i’ll go on a date w/ you to any of these! and then we can find men to go on dates with. haha.

    • #
      Bianca Garcia posted August 7, 2014 at 2:41 pm

      Pretty boys in suits and scruffy boys with tattoos, watch out!!

  5. #
    Alaina posted August 7, 2014 at 5:23 pm

    Love these tips! I’m always looking for ideas for fun dates with David. :-)

    And of course, I would love to hang out with you again, too!!

    • #
      Bianca Garcia posted August 9, 2014 at 9:04 am

      We should plan a burger date soon :)

  6. #
    Choc Chip Uru posted August 8, 2014 at 12:02 am

    Haha now I just got to find a date in Boston ;)

    Choc Chip Uru

    • #
      Bianca Garcia posted August 9, 2014 at 9:04 am

      I’ll be your date, girl friend!

  7. #
    dixya posted August 8, 2014 at 9:46 am

    i like going to casual places for dates..but wouldnt mind fancy places once in a while.

    • #
      Bianca Garcia posted August 9, 2014 at 9:05 am

      Hi Dixya! I’m the same, I usually prefer more casual places but wouldn’t say no to the fancy ones either :)

  8. #
    Pamela @ Brooklyn Farm Girl posted August 8, 2014 at 12:33 pm

    That burger! Those Mexican Cheetos! Oh yummy yum yum!

    • #
      Bianca Garcia posted August 9, 2014 at 9:05 am

      Thanks, lady! Have a great weekend!

  9. #
    Molly Galler posted August 8, 2014 at 3:15 pm

    Absolutely love this list. From one single girl to another, high five. Is there anything better than horchata?

    • #
      Bianca Garcia posted August 9, 2014 at 9:06 am

      HIGH FIVE!!

      Maybe a horchata cocktail? ;)

  10. #
    Molly Galler posted August 9, 2014 at 11:49 am

    A horchata cocktail? Hell yes!

  11. #
    Monet posted August 10, 2014 at 12:03 am

    What a great list! Ryan and I want to go back to Boston soon, and I’ll definitely consult this list!

  12. #
    Rachel cossar posted August 11, 2014 at 8:12 am

    Fab list Bianca!
    I am about to write one for The Daily Meal too:) Hope you are well!

    • #
      Bianca Garcia posted August 11, 2014 at 11:41 am

      Thanks so much, Rachel! Hope to see you soon! xo

  13. #
    Samantha Angela posted August 12, 2014 at 10:11 am

    Boston has some pretty amazing restaurants. You’re lucky to have access to them.

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