Today I’m rounding out our “best of” series (you can check out DC here and Philly here). To recap, we’re providing some of our favorite first date spots in our lovely cities. Up today is the best city of all, Boston. The Charles River is swimmable again, the Big Dig is over, our former mayor is affectionately known as Mumbles Menino, the ducklings get dressed up for every occasion, Boston is one of the best walking cities there is, etc. etc. The only thing keeping Boston from perfection is the baseball team that plays here (but not the ballpark, I love Fenway). Anway, let’s get to it.

D’s TOP THREE BOSTON DATE SPOTS

1) Granary Tavern (170 Milk Street, Boston, MA 02109 – Financial District)

Obviously, a good bar is a standard go-to for a first date. It’s a public place, it doesn’t have a time commitment, alcohol helps with nerves, etc. If it’s going well you might end up a little drunk and almost miss the last train home because you’ve totally lost track of time (this happened to me a few weeks back, on what quickly became my best first date ever). If the date is a dud, you’re out as quickly as you can down your drink.

Source: Huffington Post

This kid is going to be a CHAMP when he gets to college. Anywho, Boston is certainly not lacking in bar options, with a pretty even spread of shitty, mediocre, and great. I actually LOVE dive bars, but since my favorite one closed years ago (RIP Our House West), and people tend to have strong opinions about dive bars, I avoid them on the first date. Like S, I like a casual place that’s not too loud, and has a decent menu if the date is going well. I also like a bar that isn’t full of 22 year old assholes, a population that Boston has in spades. We are a young city full of colleges. Which was GREAT when I was going to college here (Go BU!), but now that I’m less than a month from 30, I’m over those shenanigans. So, that eliminates every single bar in Faneuil Hall, and virtually all of Allston/Brighton.

But we’re not talking about the worst of here today, we’re talking about the best. So I present to you: Granary Tavern. It’s in the financial district, so it’s easily accessible by T. But it’s also on the fringe of the Financial District, right on the Rose Kennedy Greenway, so there’s lots of other stuff around in the evening. It’s got a good selection of beer on tap, as well as wine and other cocktails. They’ve got a good menu, including a late night menu. And they’ve got a decent amount of space. Also, they have outdoor seating in good weather, that faces out to the greenway. 

Who wouldn’t want to sit out there with a cold drink and a cute guy? I love dining and imbibing al fresco. 

I also love Eastern Standard in Kenmore Square. They have insanely delicious cocktails. But it’s much trendier and gets really crowded, eliminating it from contention as my favorite. But it’s a decent back up on the right night/with the right date.

2) Sacco’s Bowl Haven (45 Day Street, Somerville, MA 02144 – Davis Square)

I also love a good activity date. Sitting across from a stranger drinking a beer can be super awkward. It’s nice to have a distraction, something that engages you both. And for that, I love me some bowling. Perhaps it’s the fact that I grew up in a town where bowling and woods parties were basically all we had to entertain ourselves. Perhaps it’s my intensely competitive attitude (my desire to win, at everything, while likely a character flaw, is also such a huge part of my personality that it’s one of the few parts of my crazy that I put on full display from the beginning to weed out the people who don’t find it charming). Almost definitely, a part of it is that my butt looks slammin’ in jeans, and bowling provides a lot of opportunity to put that on display. Besides, New England has the ever-charming and quirky candlepin bowling.

It seems like it might be easier, but it’s not. Here’s a delightfully 80’s tutorial that I came across recently while trying to brush up on my skills before a bowling date, as I had talked a LOT of trash leading up to the date (despite the fact that I’m a mediocre bowler, at best). 

There are a couple of places to bowl in Boston, but my favorite by far is Sacco’s Bowl Haven in my old ‘hood of Davis Square in Somerville. Right on the red line, Sacco’s is also easily accessible by T. They only have candlepin, so if you’re not a New England bowling purist, you’re better off going to Jillian’s or Boston Bowl. In addition to candlepin, Sacco’s has alcohol and delicious flatbread pizza. I dare you to find something wrong with the combination of beer, pizza, bowling, and healthy competition. Although they keep a certain number of lanes open for walk-ins, Sacco’s gets crowded fast, so midweek is best for this. Sacco’s will take your number and call you when a lane opens up, so if there is a wait and the bar is crowded, head over to Red Bones (or any one of the numerous other places in Davis) for a beer and/or food. 

3) Castle Island (at the end of William J. Day Blvd. in South Boston)

Since it’s summer, and summer in Boston is lovely (humid as fuck, a specialty of the eastern seaboard, but all the colleges are out and there’s an abundance of parks and waterfront to explore), I’m rounding out my fave first date spots with an outdoor activity. A little vitamin D, a little physical activity, and endless options for ways to continue the date if things are going well. I’m partial to Castle Island for this.  

It’s not actually an island, so if the date is a dud you’re not actually marooned with the fool. It’s got great views of Boston Harbor and the harbor islands, as well as the city skyline (especially if you walk out on the causeway in Pleasure Bay (I hate that name, so much, but I digress)). They open up Fort Independence in the summer, and who doesn’t love exploring a good fort? A nice sea breeze is always refreshing. If the guy is in fact a dud, you can call it a day after one lap around the fort, and at least you got some exercise! If it’s going well and you get hungry, Sullivan’s is right there with seafood, burgers, and ice cream (in case you weren’t sure you were in South Boston, that name should give it away). There’s no bar at Sullivan’s, but a quick walk into South Boston will give you plenty of options if you want to cancel out all that strenuous walking with a cold one.

So there you have it – LSD’s Best Date Spots in our respective cities. Thanks for tuning in while we share our recs! Next week we’ll be back to our regularly scheduled programming of dishing about boys, insane messages, and memorable dates (both good and bad), because those things just keep on coming.

P.S. Boston peeps, did I miss any gems you want to share? I’m all ears in the comment section!