I’m also curious, a lot of the “good” places mentioned here are mostly booked on Valentine’s Day

not sure if they’re having a special event, but courtland club might have jazz that night (and nimki’s food is great for dinner) - keep an eye out!

Gracie’s.

Definitely CAV. Their prices are very reasonable too.

Nowhere -- going out on Valentine's Day or the weekend around it is generally not good.

You will have a much better experience going to any of these places generally any other time.

A.) Whatever you pick, make reservations right away. If you don’t have resys, enjoy KFC.

B.) My recommendation is Mariel if you have the $. If you perfer seafood, hit Row 34. Also, a little more affordable than Mariel but still great is Dovetail in Charlestown.

So the thing about Valentine’s Day in the city is that everyone is going out for valentines day in the city

You are gonna be slammed into a table nuts to butts with zero elbow room, and are likely gonna be rushed though an overpriced meal and up on outta there

This recommendation may or may not work in your specific situation, but see if your girlfriend would be willing to go a day or two early. Definitely still spend actual valentines together, but you’ll get literally none of the bad stuff I described above, and be able to experience a nice restaurant in town the way it was meant to be

Oh, and beehive is dope. Good choice

Going out to eat on Vday is for rookies. Cook for her at home then get a BJ on the kitchen table.

Nautilus Oleander

What kind of food does she like?

tony and elaine's in the north end is great, i also really enjoy stillwater! southern style food near south station.

Sacco's Bowl Haven in Davis Square

Lucky Strike in Somerville. You are also close to shopping stores nearby as well to do something before or after, if you have time, if you start earlier.

Brighton Bowl at American Flatbread. It’s candlepin bowling.

I still like Kings Back Bay location.

Urban Wild in Charlestown.

If price isnt a problem the Shipwrights Daughtsr in Mystic is AMAZING. They have a Michelin star chef that creates special dishes. I’m not sure if they’re doing the preset menu that day but definitely worth looking into.

go to your usual spot where you guys actually enjoy the food and drinks… you’ll be able to have a great talk too as it wont be too busy and you’ll save tons of money on valentines “pris-fix” bullshit small portions sub par food . not being a grinch, just logical

I saw an ad for The Keg doing a Valentines menu for $70 per person, but it’s 2 course salad starter and steak & lobster tail dinner, no dessert included.

Protip: go out for dinner on the 13th or 15th instead if your partner is logical

Might not be “special” to some but Cactus Club usually does something.

Boston pizza does heart shaped pizzas

What's your vibe? Are you young, city-dwelling folks who keep trendy and like going to hip "best of town up-and-comers? types? Are you more suburban folks who like the classics done great (steak house, italian pastas, etc. in restaurants that have been around for a few decades?).

Are you looking for a "Boston Classic" meal? Or, something that's more like in line with the best meal you two enjoy, and you'll have that kind of meal in Boston?

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There are so many options/directions to go in - if you provide some parameters, I can make some recs!

Can’t recommend Talulla enough, if you’re willing to go out further to Cambridge. It’s very small/intimate (12 tables), has made it into several of the “most romantic restaurants in Boston” lists. The chef owns the restaurant and his wife is the sommelier. Giulia (also in Cambridge) is also phenomenal food, atmosphere, and service, although difficult to get reservations.

I think Sarma is the no-brainer option. It's relatively new (5ish years?). It consistently wins best of boston. If there's a national/international list of "best restaurants in each state, etc.) - it's almost always the one that is selected.

It's just a really great spot - with a awesome atmosphere. It's not formal or pretentious. The only downside is that it's not in the most walkable neighborhood. You'll definitely need to cab there/back.

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I think u/Zealousideal_Foot562 makes all great recommendations as well. I'd just add:

• The Beehive in the South End - elevated southern comfort food with live music (jazzy, bluesy trios, etc.) and a great bar menu. This is also a fun neighborhood for a night out - lots of restaurants and shops (that will be closed by dinner tiem - but, fun for day shopping).
• Meyers+Chang in the South End - Asian fusion small plates. Been around for a 10+ years and still one of the best restaurants in Boston.
• Davis Square (a neighborhood/stop on the Red Line subway) is an awesome spot for food hopping: Saloon is a speak-easy style cocktail bar. Painted Burro is a fun, trendy mexican food. Five Horses Tavern, Elm Street Taproom, and Foundry are all contemporary gastro-pubs with awesome beer lists and upscale pub food. Dragon Pizza is the best slice in Boston. Highly recommend doing a food/bar hop in Davis as a night out. Don't eat too much any where - just hit up the bar at a bunch of places.
• The Hourly Oyster House is in Harvard Square and is an awesome seafood restaurant if you want classic boston/new england options but don't want Legal Seafood.

Does she likes books? You can make reservations for hight tea in the boston library and its quite cute the surroundings of the library are very beautiful too :)

take him to a4cade after dinner! It's a great Barcade with lots of vintage games :) located in Cambridge

Papa Geno's in Brockton is where you go for your first date, though. Gotta keep it reserved for that early relationship vibe.

Bit Bar up in Salem might be up his alley if he’s into classic arcade games. It sure about romantic but I’d love to be proposed to there!

Napoli Villa in Beech Grove has great Italian food, and it's inexpensive.

This is going to sound weird, but Vicino’s food is great, but if you’re a shorter person, the table height will make you feel like a toddler.

Mama Carolla’s, Geraldine’s

Tinker Street!

Vida, The Meridian or Petersons

Lots of Bluebeard mentions. The food is good but it’s not a romantic environment. Pretty casual and crowded.

Capo is Italian and it’s dedicated gluten free on Tuesdays! The downside is that would your dinner would either the 11th or 18th this month.

I was going to say Legal Seafood, but I figured this'd be more helpful:

https://www.findmeglutenfree.com/us/ma/boston

You should check out Phil Hates Gluten on instagram. He’s posted about Italian spots in Boston 

Try the apps -- "Find me gluten free" and "gluten dude"

You could go to Bisuteki, which is a hibachi restaurant in the Marriott Hotel in Cambridge. There’s a lot of reservations available on Valentine’s!