A Little Harbor Island right in the FiDi
Because nothing impresses hotel guests like alluring tales of dead pirates hanging from the gallows, the folks behind the Sea Dog Brew Pub opened Nix's Mate, a lounge/ eatery slinging cocktails and New England farm/ ocean table fare in the FiDi Hilton's former Caliterra. The new name comes from the infamous wee Boston Harbor Island where pirate chief William Fly's body was gibbeted to serve as a warning to pirates, and to make others look up the word "gibbeted".
So as to not get gibbeted yourself, memorize:
The Vibe: Like the way you were described in Outward Bound peer reviews, the expansive, high ceiling'd space is bright & woodsy, and boasts enough reclaimed maple & dark walnut (some from the Boston Pier) to outfit a, um, hotel lounge/ eatery, as well as Mason jar light fixtures, a 22-seat stacked-quartz bar, and a private dining room adorned with the legend of Nix's Mate scripted Declaration of Independence-style across the back wall.
The Drink: As approaching lonely hotel guests is done best with booze, partake of 25 or so beers (eight draughts) like Geary's Porter, Nix's Mate Light, and Shipyard Export Ale, or kickstart the evening with a cocktail, including the "head spinning" rum & apricot brandy Hangman, or a bourbon & muddled mint number dubbed the Deliverance, presumably because it'll make you squeal like a... person who just had a pretty good cocktail.
The Food: Because friends don't let friends stay skinny, fill your belly with everything from grilled beef sirloin w/ blue cheese mashed potatoes and balsamic beet brown butter, to a ham hock flatbread w/ spinach and Provolone, to spicy mustard-topped roasted veal that's just perfect for one person, in case your date ends up leaving you hanging.