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Best first date restaurants (what's a first date)?

So I've been recently deposited into the real world dating scene for the first time EVER. Needless to say I am completely mortified and without clue. Dating savants of the Boston Board, I implore you!

Phew, that was cathartic. Quick background, I'm mid twenties male and am not interested in women impressed by Newbury Street dreck. Live in Cambridge, anything there, Somerville, Boston or Brookline is fine. Now here's the type of place I would think (probably incorrectly) would make a good first date spot:

- Good to great menu that won't scare off conservative eaters but offers some more interesting options (says "I'm considerate and laid back but totally down to eat some brains")
- Fairly good buzz of people during peak hours but not a deafening roar (in anticipation of any number of awkward pauses)
- Cozy, somewhat romantic (I don't stand a chance, but just in case)
- Entree price point in the 20s or under (don't want to seem garish or put undue pressure on the first date)
- Reasonably good wine list or good beer/cocktai list
- Takes reservations (not a must-have)
- Generally makes me look totally awesome

I haven't been eating out that much recently, so newer spots in particular I'd love help with. Applying my own criteria to my own brain, I come up with places like Highland Kitchen, Hungry Mother, Green Street, Dali, Orinoco, Coda, B&G Oysters, Metropolis.

Come on you chowish flirts, bring it!

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Highland Kitchen
150 Highland Ave, Somerville, MA 02143

Hungry Mother
Cambridge, MA, Cambridge, MA

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  1. Given that you are clueless; that makes you a male.

    i would just take them for coffee; talking to her, you should be able to determine where to take the woman on a second date. The way the world works is that women make the decision, and nothing you buy; no fancy or romantic place you take them will make a difference. And that includes women on and off Newbury Street.

    And of course, the male of the species has to pay for the privilege of spending time with a woman for a couple of dates.

    2 Replies
    1. re: cambridgedoctpr

      I generally agree with cambridgedoctpr: if you're in your mid-twenties and looking for a serious relationship through dating, plan on going on _many_ dates. Since you'll be going on a lot of dates, I recommend coffee or drinks for dates #1 and #2, and keeping them to an hour - maybe ninety minutes. You and your date will have some idea of whether you want a second date in the first ten minutes; short dates mean you don't get stuck with someone you don't like, short dates prevent over-swooning and scaring your date (or v.v.)

      (You didn't ask, but I pay for the first two dates, and if my date offers to pay - they usually do - I respond with "this one's on me, but if things go well, how about you plan and pay for the third date? This lets your date show off their interests, keeps things equitable, and encourages the best of both traditional and modern gender roles.)

      So for first dates, I suggest:
      Japonaise Bakery in Porter Exchange (ultra bonus points for cultural awesomeness, with safe options)
      Danish Pastry House in Medford
      Trina's Starlite Lounge for a drink
      Highland Kitchen for a drink
      River Gods for a drink (aim for non-crowded times)

      But to answer the question as you asked it, without imposing my above advice?

      Dali - you can show off by ordering rabbit, she can have the safe chicken croquettes
      Highland Kitchen
      Trina's Starlite Lounge

      I also recommend playing the "badass who knows the secret hole in the wall" card with:
      Wang's
      Taco Loco on Broadway
      Vinny's at Night (you ultra hipster, you)
      Pho 'n' Rice (learn to pronounce and eat pho before going)
      Cafe Mami / Japonaise Bakery - cheap, hip, both have "safe chicken" and "adventurous adzuki bean" options. (it's super effective!)

      Report back!

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      River Gods
      125 River St, Cambridge, MA 02139

      Highland Kitchen
      150 Highland Ave, Somerville, MA 02143

      Danish Pastry House
      330 Boston Ave, Medford, MA

      Japonaise Bakery
      1020 Beacon St, Brookline, MA

      Cafe Mami
      1815 Massachusetts Ave Ste M4, Cambridge, MA 02140

      Taco Loco
      301 Lancaster St, Leominster, MA 01453

      Trina's Starlite Lounge
      3 Beacon St, Somerville, MA 02143

      1. re: enhF94

        Hey, I like this kid, and he should know, Taco Loco is not a date place. I live around the block and go there often for take out...you order at the counter and wait, and then you either take it home or eat it at another counter while watching Spanish TV and jostling with crowds. No alcohol, and not a coffee place either. Although I like it ok, it is not Mexican food, nothing like Angela's in Eastie, and I've never understood why it gets such great press. I'm glad I live nearby when I want quick take out, but if it's a date place, it would be bringing home some nice huevos rancheros for breakfast in bed.

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        Taco Loco
        301 Lancaster St, Leominster, MA 01453

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      1. The original comment has been removed
        1. Rendezvous, Harvest, Casablanca, Craigie on Main, River Gods, Koreana, Monday Bar, Tamarind Bay, the wine bar next to Flour in Central Square, or, best of all, cook something simple for her, buy a good bottle of wine, and you'll be amazed by the results.

          www.shrinkinthekitchen

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          Tamarind Bay
          75 Winthrop St, Cambridge, MA 02138

          River Gods
          125 River St, Cambridge, MA 02139

          Koreana
          154 Prospect Street, Cambridge, MA 02139

          Craigie on Main
          853 Main Street, Cambridge, MA 02139

          1. The original comment has been removed