Feel chic but never awkward at posh Union Bar and Grille. This South End eatery never fails in offering you not only a gorgeous meal (albeit sometimes $), but a chance to get some good people watching in as well. The sleek and modern surroundings are the perfect backdrop to the creative menu and festive drink list. Go ahead, lose yourself in a fruity martini. Don't miss their inexpensive brunch on Saturdays and Sundays. Be part of the chic and overtired crowd that comes pouring in late morning in dire need of a cup of coffee, or better yet, a strong bloody mary. October Special: 5 year Anniversary Celebration all month Join the bartenders at Union Bar and Grille all through the month of October for specialty cocktails for $5 and complimentary nibbles between 5:30-7pm

Hidden away on an unassuming street in the South End, this trendy but friendly after-work dinner-and-drinks spot is clearly the place to be for locals in the know. Franklin Cafe only has 9 tables, so be prepared to wait 45min. to 1 hour to be seated—the fully stocked bar is a good distraction, and you can eat there if you're in a hurry. The wait, however, is worth it. Wonderful warm bread with a delicious hummus spread will start you off, best followed by one of their light salads or somewhat larger appetizers ($5-9). Entrees ($14-19) consist of straightforward meats, poultry, and fish, grilled and basted with imaginative sauces; try the steak with chive mashed potatoes and a mountain of fried red onions ($18). Although the menu, which changes seasonally, features only 1 vegetarian entree, the waitstaff will happily make substitutions or alter the daily special. The only drawback is that the kitchen is too small to produce desserts, which, after the great dinner, often leaves you craving something sweet. If you're really in a jam, settle for a sweet martini ($7)—there's a reason a martini glass is on the sign. This section contains information from Harvard Student Agencies' Unofficial Guide to Life at Harvard.

Another trendy and cutting edge restaurant to add to the hot, hot, hot South End dining scene. Along with sophisticated designer lofts and apartments, Banq is opening in the beautifully renovated Penny Saving Bank. Decor is made up of undulating layers of sand colored wood that flow across the ceiling like a soft wave. The restaurant is like the inside of a prehistoric whales body, as depicted by a minimalist Japanese architect. Very chic, spacious, loud and almost anonymous; it could be a spot in midtown Manhattan. You're likely to spend probably 10 minutes staring around at how interesting the space is. Little plants at the tables are a nice added touch that don't get in the way of your food. Which, by the way, is impressive in an Iron Chef sort of way. If you have friends visiting from NYC or London or Tokyo, bring them to Banq to show them that 'lil ole Boston IS a cutting edge Metropolitan city.

Hidden away in an innocuous-looking building in the South End, this theater-restaurant offers up a truly original dining experience. A troupe of second-rate actors, musicians and comedians dressed in ridiculous Middle-Age costumes perform a series of raunchy skits and songs. During the performance, the actors somehow find time to serve up a not-quite-authentic medieval meal including vegetarian “dragon” soup, spiced shrimp, strips of beef, and roasted herbed chicken, all of which is eaten without knife, fork, or spoon. You may also enjoy complimentary beer or wine with some ticket purchases, and you'll need plenty of it to really get the most out of the show. If you go with a large group, you just might have a great time. 21+, so make sure you bring your ID or a parent. Admission (which includes the meal but not the tip) ranges from $25-45, with the higher prices on weekends. Reservations are required. Private parties of up to 90 are available. This section contains information from Harvard Student Agencies' Unofficial Guide to Life at Harvard.

Sage Restaurant is a cozy and intimate setting in one of Boston's oldest neighborhoods. The restaurant rivals the uptown establishments by delivering American and European style cuisine that is both modern and classic.