Finding a first-date spot is tricky. You want the place to feel fun but not forced, with reasonable price points lodged between “penny pincher” and “moneybags.” The Gallows is always a perfect match. The reliably buzzy South End gastropub has a liveliness that lubricates conversation (creative cocktails help too), and shareable plates like loaded poutine and pork belly pinchos suggest a noncloying sense of humor—just like a good date does.
1395 Washington St., Boston • (617) 425-0200
2016 Winner: Wink & Nod
This sexy, animal print-accented subterranean speakeasy is lit low enough to encourage smoldering stares over the rim of a stiff Scotch cocktail...
- 3 Appleton St., Boston
- (617) 482-0117
2018 Winner: Lion's Tail
- 354 Harrison Ave., Boston
- (857) 239-9276