Canary Square
The industrial-chic dining room is a cross-section of young families, couples, and groups of friends, all of whom come for the fun fare and serious craft beers. What to Order: The grilled hanger steak; pulled-pork tacos. 435 S. Huntington Ave., Jamaica Plain, MA canarysquare.com.
Square Cafe
What may be the South Shore's most fetching dining room (white tablecloths, cherry hardwood floors, plaid banquettes, soothing antique prints) now sports an equally alluring menu. Chef Andrea Schnell, an alumna of Duxbury's Windsor House, whips up newfangled, delectable New England favorites. The sweet, juicy tuna with chile vinaigrette alone is worth a visit. All's not perfect: The service here still needs work, and on some busy nights delivery can be slow. But between the convivial atmosphere and the pretty room, there's no better place to kill those extra minutes. 150 North St., Hingham, MA thesquarecafe.com.
Siam Square
The atmosphere isn't much, but the food is. Ask for the brown menu—reserved for Thai diners—and order the Steamed Mussels, the Tod Mun fish pancakes and the Green Papaya Salad with Sticky Rice (roll the rice into a little ball with your fingers and then dip into the papaya). 86 Harrison Ave., Boston, MA .
Gargoyles on the Square
Neither plain nor pretentious, this enchanting and candlelit treasure is a lesson in presenting good food with muted sophistication. Dishes including grilled salmon with tomato-tarragon butter or black-pepper pappardelle with chicken confit, fennel, and spinach, are as warm and agreeable as the earth-tone décor, while the bar menu shines with reasonably priced treats like frog legs with baby broccoli and oyster poboys. The room is cozy enough that finding a table on weekends can be competitive, but locals know the strawberry rhubarb croustada is worth lingering over. Besides, with such a lively bar, the wait is half the fun. 219 Elm St., Somerville, MA .
Gargoyles on the Square
Visiting Gargoyles only on date night (yes, the lighting flatters; true, the velvet cascades) is like eating oysters only to boost your mojo. Both should be enjoyed, and often, on their own merits—nooky prospects be damned. Wash away the workday with a silky but strong cocktail (we love the summer-in-a-glass Backyard), and refuel for tomorrow with chef Jason Santos's seasonally inspired fare. And, if you must, flirt at the dish sitting at the next table. Somerville, MA 2144,
Gargoyles on the Square
Despite the name, hardly any Goth influence exists at this intimate Davis Square hangout. In fact, the bar and adjacent dining room are welcoming digs with floor-to-ceiling café windows and walls painted in earthy browns and reds, more sophisticated and friendly than dark and scowling. The menu is equally approachable, with such thoughtful combinations as chile and honey-grilled salmon, braised short ribs, and Cervena venison with aged Vermont cheddar, celery root, and apples. It's no wonder this spot is always humming with denizens, dressed in black or not, of its diverse surrounding neighborhood. 219 Elm St., Somerville, MA .
Square Café
Suburban restaurants often thrive precisely because they're away from the city: A captive audience takes what it can get. Square Café by contrast, could compete fiercely in any Boston neighborhood. This New American eatery radiates a laid-back confidence born of a masterful affinity for different cuisines. Another compliment, and one that may come out wrong: Menu descriptions that sound like overwrought disasters ('stuffed pork chop with spinach, prosciutto, cheddar and cornbread stuffing, sweet potato-vidalia gratin, and golden raisin demiglace') turn out to be carefully calibrated balancing acts of texture and flavor. 150 North St., Hingham, MA 2043, .
Upstairs on the Square
Amid pastel-colored walls (so charming!), fireplaces (so cozy!), and food like Wellfleet oysters on the half shell with yuzu ice (so flirtatious!), what makes this the Hub's most romantic option is the space. Specifically, that there's lots of it. Amorous ambiance is so often ruined by patrons who are positioned a little too close and talking a little too loudly. At UpStairs on the Square, it's private enough to murmur juicy tidbits and sweet nothings with abandon. 91 Winthrop St., Cambridge, MA 2138, upstairsonthesquare.com.
Harvard Book Store
Just can't find that book you want? They'll almost certainly have it here. One of the last of Harvard Square's great independent bookstores, the Harvard Book Store is still run by the son of the man who founded it in 1932. It's stacked to the ceiling with texts, including an expanded selection of popular fiction and nonfiction, but also highbrow and specialty works you'll never find in the megachains at the mall. The knowledgeable staff will help you find the one you're looking for, climb one of the rickety wooden ladders to retrieve it for you, and more than likely offer a review. Downstairs is one of the best remainders departments in the country, along with well-preserved used books. The New York Times and in-store bestsellers are 20 percent off, as are 50 titles each month recommended by the store's buyers and booksellers; remainders are from 50 to 80 percent off the original price. 1256 Massachusetts Ave., Cambridge, MA harvard.com.
Milky Way Lounge & Lanes
Dyke Night impresario Kristen Porter comes up a winner either way, as the only worthy contenders here are Second Saturdays (at bouncin' Fenway nightclub Machine) and Menage à Trois, a.k.a. Fourth Fridays (at J.P.'s Milky Way), both dance events that she masterminded and that feature her stellar roster of female DJs. Though Machine's got by far the bigger crowd and the pole dancing (oh, the hotness), the indie-cool Milky Way's got our heart. Maybe it's the lounge's factory-chic new digs at the Brewery Complex. Or that the small space makes things more friendly and intimate. Or maybe it's just the irony of having all this gynomite going off next to a towering defunct smokestack. 284 Amory St., Jamaica Plain, MA 2130, milkywayjp.com.
The Book Case
A musty remnant of our literary tradition, a haven for mourners of an earlier age when books were read. And most of these were read. 42 Church St., Cambridge, MA .
Commonwealth Books
How lucky are we to have two legit contenders for this category, in the Brattle Book Shop and Commonwealth? Both boast thousands of titles and terrific prices. Yet Commonwealth wins for being a bit easier for casual collectors to navigate. (Connoisseurs, though, should make it their mission to frequent both of these worthy independents.) 526 Commonwealth Ave., Boston, MA 2215, commonwealthbooks.com.
Davis Square Plaza
There’s no better place to hang out when the sun’s out, so grab a cone at J.P. Licks, find a comfy bench, and enjoy some of the best people-watching and outdoor performances on this side of the Red Line.
Kendall Square Cinema
Enjoying the artistry of independent cinema doesn't have to mean enduring drafty old theaters. The Kendall Square is as state-of-the-art as any megaplex, but with niche amenities like baked goodies from Dancing Deer Baking Company and green tea. Sure, the tickets and concessions are a little pricey, but inside the nine intimate Dolby Digital Surround EX theaters, the seats are comfy and come equipped with cup holders. Cheap parking and a convenient shuttle from the MIT-Kendall Square T stop make getting there a cinch. One Kendall Square, Cambridge, MA landmarktheatres.com/market/boston/kendallsquarecinema.htm.