Go Boston: Where To Date
My friends are laughing right now. I won't tell you why but... I think you can figure it out.
Okay I barely dated anyone in college, that's why.
Nice To Meet You
City Bar @ The Lenox
Leading off with a pair of solid go-tos in case you don't have a ton of time to plan (and/or don't care too much about originality...you should), first up is City Bar at The Lenox. Ambiance, good to great cocktails, fancy old hotel in Back Bay, never too crowded, check check check aaaand check.
The nice thing about Towne besides the delish food is that it gives you options: entrance bar, restaurant bar, or upstairs party bar? For a first date I'd stick with the first bar, as it's populated but usually a little quieter than its comrades (you can often find the finance bro crowd upstairs). That is, unless you don't care about listening to your date, in which case we have bigger problems to address.
If you know your date's not looking for the standard - dark bar, lots of people, intimate table, crazy cocktails that take too long - then I'd try Felipe's Taqueria in a heartbeat. Right on Harvard Square and offering solid snacks and probably the cheapest roof deck in Boston, this is just the place to switch up your first date game for the summer.
You're showing off a few things when you invite someone to Toro: you like food, you know your restaurants, and you've got general good taste. Now have tapas. Have wine. Have good time.
Drink is really very so cool. With no set cocktail list, either name your favorite, ask what's good today, or tell the bartender what you like and let them whip up something new.* Between the cocktail focus and food by Lydia Shire (of Towne & Scampo) this new(ish) Fort Point establishment was practically built for the first date.
*Note: Don't do this at just any bar. Especially when there's a million people pressed up to the counter all clamoring for drinks, the LAST thing a bartender wants to hear is, "Uhh I like whiskey and vodka? Surprise me!"
It sounds like a standard date locale - dark, intimate, crazy cocktails - but Shojo Flying Tiger Palm Strikes that description right out of the air. For one, there's an ever-changing mural on the back wall (with a tiny window for the kitchen right in the middle), and old kung fu movies on loop behind the bar. Then there are the cocktails: Yakuza Old Fashioned & Kusarigama for the whiskey lovers, The Jade & Orizuru Fizz for the shochu fanatics, among others. And the food (get the ribs) will leave you in silence; not the awkward kind.
I Like You
Parla should be on everyone's date list. As the coolest bar in the North End (aside from Mamma Maria's cozy 5-seater), complete with speakeasy vibes and drinks that match up to the ambiance, this is a perfect place to start or finish a night out. Plus you can show off how adventurous and/or nerdy (mostly nerdy) you are by rolling a 20-sided dice to decide your drink. Heyo.
While much more casual than its NYC namesake, Babbo Pizzeria is still a swanky joint; just more young-swank than swank-swank. You know what I mean. Anyway Babbo specializes in shareable, delicious Italian and bottles of great wine - and it's in Fort Point! So hip. So now.
They've got the food, they've got the live music, they've got the bar scene, they've got a massively cool subterranean buildout; The Beehive is practically cheating when it comes to date night. Cons: can be loud, bro-y, and pricey. Good for more relaxed dates (good luck w/ that).
Little Donkey is the current talk of the town, and if you haven't been there, you've been left out of the conversation (see what I did there). By the same guys that brought Boston Toro, Uni, and Coppa, Little Donkey is another sharing-focused restaurant, but this time it's contemporary American. With a short but rockstar menu and cocktails including a grapefruit drink in a literal grapefruit, Little Donkey is a fantastic set-up for good times.
What everyone likes to call "Boston's New Backyard" or whatever, Lawn on D is actually a genuinely great spot to hang out, especially in the summer. Between the outdoor bar, music, and the ever-Insta-worthy neon swings, the Lawn should be everyone's go-to summer alternative to whatever booze hole you've been hiding in for the last six months.
Get it? Like, the secret sign for a speakeasy? You actually have to do that to get in.* Accessibility aside, South End's Wink & Nod is exactly the half-classy, cozy cocktail lounge you need that says "For real, I actually like what's going on with this you-me thing here." Or something smoother than that.
*No you don't, don't do that. Or do, I'm not the boss of you. But that bouncer kind of is.
Uni is good no matter when, with some of the best sushi in town, but if you come on Friday or Saturday night (starting at 11pm) you can treat yourself to one of the best ramen bars in town. It's a pretty half-hearted "secret," but still not too hard to get a seat. Think of this as an opportunity to see how adventurous and/or uninhibited your date is (do they slurp? If yes, keep 'em). Ramen is best enjoyed as a vehicle for sobering on your way home, with a beer to soften the salty, porky blow, so plan your night accordingly.
I Like Like You
This is where you take someone when you want the location itself to say, "You are the special occasion" ("Ewwwww" - Ten-Year-Old Mitch). On top of some of the best Italian in a city full of great Italian, Mamma Maria has excellent service, a superb wine list, and a comfortable, homey atmosphere. This place will leave an impression.
Boston's hottest new rooftop party food zone is Terra! (*throws up a little*)
Nah, but it's cool. Terra is the rooftop grill and bar at Eataly, Boston's latest celebration of all things Italian and food. Recently opened, it is highly recommended to get a reservation before turning up at the host stand at the bottom of the stairs, only to get a half-hearted smile and a "#Sorrynotsorry, no tables." Come for apps and drinks or full-on dinner, but share everything; it's a magical menu out there, Hobbes ol' buddy... let's go exploring!
This is one of the best (and one of the few) rooftops in Boston, that much is for sure. Is it douchey? You betcha. But the views of Downtown Boston from this particular hotel make it a step up from The Revere, despite the similar atmosphere. Best employed as a bookend before or after an incredible dinner nearby.
The Liberty Hotel
The jail-themed decor may give your date the wrong idea at first.* They'll get over it quickly though, because The Liberty Hotel is impressive at minimum. Inside are two bars and a restaurant: The Clink (or the general hotel interior bar), Alibi (the lounge bar), and Scampo, respectively. A great night at the Liberty Hotel moves through all three in that order, from taking in the architecture with drinks in the cavernous lobby, settling down with another round and appetizers in the more comfortable Alibi, and finally a spectacular dinner at Scampo. Cheap? Nah. Special? Yah.
*Or the RIGHT idea, eh? Ehhhhhhh? I kill me.
You can go to Bastille Kitchen for a very good, traditional French dinner. Or you can go to Bastille Kitchen's bar for an even better nightcap. It may be difficult to find a seat on the weekend, but for sheer ambiance and quality of drinks, the bar at Bastille is easily one of the best cozy spots in the city.
There, now you have a dozen places to dump your Tinder mistak- I mean, date. Got anything better? Let me know below.
Don't say Bijou.