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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!

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:
      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!

      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.

        Taco Loco
        301 Lancaster St, Leominster, MA 01453

    2. 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.


      Tamarind Bay
      75 Winthrop St, Cambridge, MA 02138

      River Gods
      125 River St, Cambridge, MA 02139

      154 Prospect Street, Cambridge, MA 02139

      Craigie on Main
      853 Main Street, Cambridge, MA 02139

      1. i like to go to the sort of places you have in mind for a first date, like green st, orninoco, central kitchen, rendezvous (sitting at or in the bar is sometimes a good option for those places), oh and maybe miracle of science. central sq is where it's at...also good for having post drink drink options if things are going well b/c the place is flush with quality joints. i recently turned thirty, date every so often, and i feel like it's a given for both parties that drinks and usually just small plates/apps are on the agenda for a first night out (unless it's decided "coffee," but i prefer drinks to loosen things up). avoid the word "dinner" at all costs for first date. other ideas: russell house tavern, garden at the cellar, stoddards, washing sq tavern (just lost their talented chef though, so questionable), eastern standard (place is great, but perhaps a bit large and cliche/popular for first date), franklin cafe, citizen public house (new place near fenway, had a really good experience there), oh and the gallows in south end (def look into that place). i scoped out highland kitchen for a potential date spot with a friend once--very very loud and busy. but i hear it's great, so i'll get back to it for nondate night.

        1. For what it's worth, a good friend was in your position about six years ago, and his "first date place of choice" was always the Green Street Grill. I think he liked to take dates there, so that only the girls were changing, not the restaurant for the first date (controlling the variables --- what can I say, we were scientists). I'm not sure I'd recommend this approach, but the Green Street Grill does have a lot to recommend it as a first date restaurant. Highland Kitchen is wonderful for food, but very loud inside; Hungry Mother is wonderful, but quite expensive. Tapas is a good choice too --- Dali is very romantic inside (all the candles), Toro has better tapas, but also a bit too crowded (you don't want to wait in the cold for an hour on a first date!); I've had very nice experiences at Estragon, and it's a nice dimly-lit setting. Tangierino in Charlestown is a very romantic setting for Moroccan food. Baraka Cafe is very homey, and is a nice, very Chowish, date place.

          That said, many of these places might be best for a second date --- starting off with coffee (or tea, bubble tea, drinks, frozen yogurt, or Toscanini's ice cream) might be easier.

          Baraka Cafe
          80 Pearl St, Cambridge, MA 02139

          1704 Washington St, Boston, MA 02118

          Green Street
          280 Green St, Cambridge, MA 02139

          73 Main Street, Charlestown, MA 02129

          Highland Kitchen
          150 Highland Ave, Somerville, MA 02143

          Hungry Mother
          Cambridge, MA, Cambridge, MA

          1 Reply
          1. re: lipoff

            Green Street is a great choice. A couple cocktails, maybe the fried yucca appetizer. You can look cool by asking for the REAL cocktail menu, not the smaller one they give to everyone.

          2. I am thinking of a non-joint kind of place. And what comes to me first is the importance of good professional waitstaff in a fairly small quiet place.Immediately I think of the waitstaff at Gargoyle's in Davis Square, gracious, friendly, laid back, but focused on serving your needs and keeping pretty invisible. The opposite of in-your-face or clumpy /"how you guys doin'?" The back room is quiet and comfy and low lit.

            In addition, the food is dependably wonderful and varied and inventive with a lot of food-chemistry elements from the hip but serious chef, Jason Santos. The many surprise elements will spur delight and give you two lots to comment on . The bartender is deservedly well known and well regarded.

            It's really good to sign up for their email list because they often offer special priced meals for their list members. For example, on Sunday we were able to have a really extraordinary prix fixe 3 course meal
            featuring an amazing cumin crusted rack of lamb, for $35 pp!!!

            1. Bergamot for dinner; dali for a drink

              1. I think you answered your own question. Green Street seems to fit your criteria perfectly. I think the down to earth neighborhood vibe is perfect for a first date. Highland Kitchen fits as well, however it can be a bit loud for conversation at times.

                1. Listen to enhF94-good advice there. Especially the part about going for coffee or drinks on the first date. That way you can make a quick getaway after one drink if it's not going well. I'm thinking of the guy with the graying ponytail from Arlington..............

                  And lose the self-deprecating humor-or at least tone it down. You sound funny and intelligent-use those strengths!

                  And speaking of the graying ponytail-any of the North End cafes is a good place to meet.

                  2 Replies
                    1. re: mtm7654

                      I definitely went out with some gray ponytails in my single days. That's why the idea of a leisurely dinner (and worse: a "romantic" dinner) with someone who is basically (or literally) a stranger at this point seems so odd to me.

                      Drinks allow for the evening to be over in several hours or 20 minutes, depending.

                      I'd also be hesitant to just have one place in mind. Green Street definitely seems like a good fit, but what if she lives in East Boston and is taking the T? That's kind of a pain.

                    2. Chowdahound, I want to hear more about what kind of women you will be dating, other than non-Newbury types. Do you want to date a fellow chowhound (in spirit if not in actuality)? What is she into? Might totally change the recommendation. I never followed the one-size-fits-all-I'm-always-going-to-Green-Street philosophy.

                      1. I always say that if I were to go on a first date again (married), I'd take my date to Toro. It's a fun place with great food. If my date isn't able to handle the slightly odd food choices and the mildly chaotic way that tapas is served, then I'd know she's not for me. There's no point in putting on an act. Be who you are.

                        1704 Washington St, Boston, MA 02118

                        1. U wiykd gi ti syoer 88, tgwn natve Carkiss.

                          5 Replies
                          1. re: Alcachofa

                            my best guess of Alcachofa:
                            I would go to super 88, town native Carcass?

                            1. re: tysonmcneely

                              LOL - I think you're close -

                              "I would go to super 88, then maybe carcass..."

                              1. re: tysonmcneely

                                Reminding me of the link I just got for the best of iphone's auto correct feature.

                                1. re: tysonmcneely

                                  His right hand is shifted over one key to the left on the keyboard, so it's "I would go to Super 88, then maybe Carlo's [Cucina Italiana]". Cryptography! I think you'd have to call that a variant of the Caesar cipher.


                                  1. re: MC Slim JB

                                    You win a cameo in the "A Beautiful Mind" sequel.

                              2. Thank goodness my dating years are behind me, but I remember it mostly fondly (this means my advice is a decade old though, so forgive me if it is out of date).

                                As a woman who kissed a lot of frogs before finding her prince, I remember specifically requesting first dates to be the coffee / drinks / limited time concept others have mentioned after several failed dates of the nature you described. The date you described is a awesome second date once you are sure you get along and have some chemistry. Dinner dates with someone that you don't click with are excruciating....be kind to yourself and her and avoid it till your sure. It's always best to go with the old adage "leave them wanting more".

                                I'd recommend Cafe Algiers in Harvard SQ for Turkish coffee or hot chocolate and some baklavah. You'll get foodie points, but save your budget and get the freedom to cut and run if it is a dud. If it is going well, you can always invite her to walk around Harvard SQ with you for a while. Good luck!

                                1 Reply
                                1. re: InmanSQ Girl

                                  Algiers also serves beer and wine now as well as some good small plates, so you could easily convert coffee into something else right on site if it's going well, and then head out to something more exciting if it's going very well.

                                2. I think your first date place is going to depend on who your date is with. If it is someone you haven't met before, drinks or coffee is perfect-- you can always extend either into dinner or a walk if you are hitting it off. For coffee-- I love Flour Bakery. For drinks, you have a variety of options-- some of the places that I frequented when dating may be out of date now but here's a couple: Silvertone, Eastern Standard, CityBar in the Lenox Hotel, 75 Chestnut or the bar at the Beacon Hill Bistro.
                                  If the date is with someone that you have met before through friends etc, dinner is great. I think the places that you suggested are great. Here are some others-- Franklin Cafe (doesn't take reservations and can be crowded but there are good backups in walking distance like Orinoco, Toro, Joe V's), Giacomo's (the one on Columbus takes reservations, it is cozy and loud but not so loud that you can't have a conversation and reasonably priced; only drawback-- cash only); Trattoria Toscana in the Fenway; Parrish Cafe (sandwiches-- but interesting ones and a really amazing beer menu).

                                  Trattoria Toscana
                                  130 Jersey St, Boston, MA 02215

                                  Beacon Hill Bistro
                                  25 Charles St, Boston, MA 02114

                                  Eastern Standard
                                  528 Commonwealth Avenue, Boston, MA 02215

                                  1704 Washington St, Boston, MA 02118

                                  Flour Bakery + Cafe
                                  12 Farnsworth St, Boston, MA

                                  69 Bromfield St, Boston, MA 02108

                                  Joe V's
                                  315 Shawmut Ave, Boston, MA 02118

                                  75 Chestnut
                                  75 Chestnut St, Boston, MA 02108

                                  1. Folks, we've removed some non-Boston-specific dating advice from this thread, and would like to ask everyone to help us keep this a great, locally focused resource by sharing chow tips specific to the Boston area. Thanks!

                                    1 Reply
                                    1. re: The Chowhound Team

                                      Any chance of restoring the parts that included my Boston-specific brunch recs?