This post was originally published February 8, 2011. I have since updated it with new insights I've gained this year, just in time for Valentine's Day!
Picking a good date restaurant can be tricky.
You want the ambiance to be pleasant, nice . . maybe even a bit fancy. Yet, the last thing you want is a pretentious, stuffy environment that makes you feel uncomfortable. You want to be able to sit back, relax, and really enjoy the evening.
Of course, it goes without saying that the food must be excellent. And, preferably the prices would be reasonably, although we may be willing to splurge on special occasions.
I've lived in Boston for 17 years and I've been with Bryan for about 15 years. Needless to say, we've been on a lot of dates in Boston, and definitely have tried a number of places in the greater Boston area.
Here are some of our favorite special occasion / date places (I've thrown in a couple from New York, California, and Las Vegas as well just for fun!).
The North End
Hand made Ravioli from Mamma Maria
We always love going to the North End. The neighborhood itself is fun to explore; it's bursting at the seams with fantastic food; and (if the weather's nice), you can take a lovely romantic stroll all the way back to Cambridge through Faneuil Hall, the Public Garden, Back Bay, and the bridge overlooking the Charles River.
Because I love to walk, a night out in the North End is one of my favorite ways to spend an evening. For a romantic night out, I love the ambiance at Mamma Maria, a quaint multi-level townhouse overlooking North Square. Mare, an Italian place specializing in seafood, is also very nice with huge windows facing out into the North End. Try the langoustine if you go there; it's absolutely delicious. Prezza and Monica's Vinoteca are also great choices, with Prezza being a bit smaller, quieter, and more intimate. 
Rack of Lamb and Grilled Langoustine from Mare
Though it's not Italian, I also love Neptune Oyster. It's tricky for a date because you can't make reservations and it gets quite crowded. Nevertheless, I love the tiny, intimate atmosphere, and the food is absolutely outstanding. Taranta, a Southern Italian / Peruvian restaurant also in the neighborhood, was ranked the most romantic restaurant in Boston by Yelp last year.
My favorite thing to do at the end of the night in the North End is to forgo dessert at the restaurant and instead opt for a nice cappuccino and a small pastry at one of the local cafes (e.g., Cafe Vittoria). Finally, stop by Mike's or Modern Pastry and pick up some cannolis to take back with you. If you still have room, you can always enjoy one on the road as you take your time meandering slowly throughout the Boston neighborhoods nearby (the waterfront, Faneuil Hall, Chinatown, just to name a few).
Cambridge / Somerville
Ragout of wild mushrooms, Farm fresh egg from Craigie On Main's Ultimate Chef's Tasting
There are so many good restaurants in Cambridge / Somerville that it's hard to just pick a few. Craigie On Main is one of my favorites and we've celebrated many special occasions there in the past, like our anniversary, Bryan's birthday, and my birthday. I highly recommend the Ultimate Craigie Experience. Just make sure you call ahead and tell them you want to have that particular tasting! You might even score ringside seats, the ones that give you a firsthand view of the action inside the kitchen!
Bergamot is another one of my favorites. Keith Pooler is inventive and is always changing up the menu. You never know what to expect! The service is excellent and the prices are very very reasonable considering the quality of the food that comes out of that kitchen!
Ten Tables and Salts are two very small, intimate places that serve high quality food. Ever since moving to the northern side of Harvard Square, Ten Tables has become our favorite place in the neighborhood to visit. The food is fantastic, the staff is super nice, and the prices are very, very reasonable.
Bondir is another fabulous option. The first time I visited, I fell in love with the warm, inviting ambiance inside this tiny little restaurant. There's a huge roaring fireplace that just beckons you to come inside - super romantic! The chef-owner, Jason Bond, comes from Beacon Hill Bistro and creates a new menu every single day.
Finally, there's a little gem call T.W. Food in North Cambridge just a little off the beaten track. The ambiance is super warm and intimate, and the food is fantastic.
Littleneck Claims and Andouille Sausage from Rialto
If you're in the mood for Italian, Rialto has excellent food in a very traditional upscale environment. If you want more old world Italian charm, then Gran Gusto in North Cambridge is perfect for that. For something a bit unique, try Oleana, which serves farm fresh dishes with a Mediterranean twist. Upstairs on the Square is also another solid, traditional upscale restaurant overlooking Harvard Square. If you don't mind something a little unconventional, I think Hungry Mother (Southern American/French cuisine) serves some of the best food in Cambridge.
Finally, if you want something just a little different, try Muqueca (Brazilian), Atasca (Portuguese), or the Helmand (Afghan). All of these are excellent ethnic restaurants that are really nice and just a bit more reasonably priced than your typical European or new American restaurant.
Boston
Maine Lobster, "Pain Perdu", Grilled Local Romaine, Dill from Menton
Barabara Lynch is sort of an icon in Boston and has some of the finest restaurants in New England. Her newest venture, Menton, aims to bring Boston's haute cuisine to a whole new level. Menton has excellent service - the type you would find in a multi-star Michelin restaurant - paired with really really good food. If you can, try booking a special meal at the Chef's Table, a unique and intimate experience that's different from eating in the normal dining room.
No. 9 Park was Barbara Lynch's flagship restaurant (before she opened Menton) and is a solid choice as well. We went there for our wedding anniversary in 2009. The service is top-notch and the food is very good. If you go, you must try her signature dish: the prune stuffed gnocchi with fois gras. Incroyable!
If you're a steak lover, Bryan thinks Grill 23 has the best steak in Boston. If you love Japanese food, O Ya has a fantastic tasting menu that's wonderfully creative, exquisitely executed, and absolutely delicious. Bryan thinks O Ya has the best food in Boston, period. Uni Sashimi Bar is also an excellent choice, and I've had multiple exquisite birthday dinners there. Oishii Boston is another solid choice for Japanese (especially if you don't feel like shelling out $100+ for a tasting menu).
A special Valentine's Day post-dinner treat at Clio
For Valentine's Day in 2010, Bryan and I tried Ken Oringer's Clio for the first time. We liked some dishes better than others, though overall we had a very enjoyable time there. Last year, we checked out a few places over Valentine's weekend, like Oishii Boston (just 'cuz I love sushi) and a pop up restaurant at the Taza Chocolate Factory, prepared by Will Gilson, formerly from Garden At the Cellar.
New York, Las Vegas, and Napa Valley
The French Laundry, Yountville, California
California
You can't beat a trip to Napa Valley when "romantic" comes to mind - rolling hills, beautiful vineyards and some of the best restaurants in the world. Thomas Keller's The French Laundry is iconic - a gorgeous, quaint farm house serving some of the most exquisite food around. I also love Redd, a more reasonably priced but perfectly enjoyable restaurant just down tbe street in Yountville. If you're in southern California, Melisse is an excellent option, having one of the most extensive bread collections I've ever seen (second only to Joel Robuchon in Vegas), not to mention fantastic food in a warm, comfortable atmosphere.
We tried Jose Andres' Saam inside of his flagship Los Angeles restaurant Bazaar this past winter. A mixture of molecular gastronomy, bold Spanish flavors, and traditional French technique, the tasting menu at Saam showcases some of Andres' favorite dishes from all his restaurants (post coming soon).
For Sushi, try Sushi Zo, an omakase only no menu sort of restaurant. The fish is excellent and the atmosphere is very authentic. It's one of closest experiences I've had to a Japanese sushi omakase here in the US (post coming soon).
Joel Robuchon, Mansion in Las Vegas, Nevada
Las Vegas
Las Vegas is the land of excess, over-indulgence, and opulence, and Joel Robuchon definitely delivers! My dinner at Joel Robuchon (both the four course and the Menu Degustation) were, by far, the most over-the-top meals I'd ever had - everything from plush velvet pillows and pearls to gold in my food and a crazy display of bread and mignardises (see above). It's a little insane, but definitely a unique experience! We also tried an excellent French meal at Picasso last January, along with some crazy good 90-day dry aged steak at Carnevino ("best steak I've ever had" according to Bryan).
If you're into really good pasta, definitely check out Mario Batali and Joe Bastianich's B&B Ristorante. The service is good, the tasting menus are fun, and the pasta is some of the best we've ever had. For a bit more traditional, old world Italian, you can't beat Raos or Il Mulino , which have all around good, solid food (even if the ambiance is a little bit more casual). Bryan and I both agreed this past January that Il Mulino is now our favorite Italian restaurant in Las Vegas (sorry Mario!).
Butter Poached Abalone from Daniel in New York City
New York
Oh New York! New York is still the mecca for food in the US. There are so many crazy good restaurants, where do I start? Well, there's Thomas Keller's flagship east coast restaurant, Per Se, which sits at the top of the Time Warner Building in Columbus Circle. Though we liked The French Laundry just a tad more, we still had a perfectly enjoyable meal here.
We celebrated my birthday at Daniel in 2009 and it still reigns as one of my favorite dining experiences of all time. The service is incredible - warm, friendly, yet super professional at the same time. The space is beautiful and the food is absolutely unforgettable. As a seafood lover, Le Bernardin is still my top choice in New York if we're just talking purely food. No one beats Eric Ripert when it comes to seafood . . . .
Well . . . that is unless you want to talk sushi, in which case I highly recommend Sushi Yasuda. The ambiance is like a normal sushi restaurant (so none of the white glove service, etc), but the food is insanely good, and probably among the best sushi in the U.S.
Eleven Madison Park (which just got its third Michelin star!) is a gorgeous restaurant with absolutely incredible food. I've had the privilege of trying Daniel Humm's food twice, and both times I was blown away by his talent.
If you can score a reservation, Momofuku Ko is a fun and unique experience. David Chang is a genius when it comes to putting flavors together. The ambiance is casual (we wore jeans), but the experience is definitely special.
For a lovely, rustic Italian-based evening, our current favorites include Il Buco Alimentari and Torrisi.
Well, there you have it - my current ever changing list of good date restaurants. I know this list is a bit biased since I tend to eat most often in Cambridge and just a bit beyond. Also, when I travel I have only a few days, so I tend to seek out well-reviewed, well-known restaurants. However, I'm sure there are tons of excellent hidden finds out there.
I would love to hear what you think.
What are your favorite date restaurants??
THE LIST FROM THIS POST
The North End
Mamma Maria
Mare
Prezza
Monica's Vinoteca
Prezza
Neptune Oyster
Taranta
Mike's Pastry
Modern Pastry
Cambridge/Somerville
Bondir
Craigie On Main
Bergamot
Ten Tables
Salts
Rialto
Gran Gusto
Upstairs on the Square
Oleana
Muqueca
Atasca
Helmand
Boston
Menton
No. 9 Park
Grill 23
Oishii Boston
O Ya
Uni Sashimi Bar
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