Change up

THE NIGHTLIFE rut: it’s a common affliction. Your summer spent traipsing all over Nantucket, Kennebunkport, and the Cape — plus Tuscany, if you’re one of the lucky ones — makes your usual haunts in Boston pale in comparison. Instead of giving in and heading to your usual bar stool for the fourth night this week, let us help: we have the tips you need to make over your nightlife in just 30 evenings out.

MP3: Heather Bouzan talks to WFNX about spending 30 nights out in Boston (right-click, save-as)

Night 1: Explore a new neighborhood. So much of your scene is determined by where you live, and it’s easy to forgo traveling in favor of a familiar local spot. But tonight, get out of your comfort zone. If you generally never set foot outside of Cambridge, experience the Southie scene: sip a cocktail at the Playwright (658 East Broadway, South Boston, 617.269.2537), then test your tolerance against the locals at the Boston Beer Garden (732 East Broadway, South Boston, 617.269.0990). Never thought you’d leave Brookline? Explore what the South End has to offer: try the Franklin Café (278 Shawmut Avenue, Boston, 617.350.0010), the Beehive (541 Tremont Street, Boston, 617.423.0069), and, if you can stumble over in time for last call, Clerys (113 Dartmouth Street, Boston, 617.262.9874). If you’ve never hung around for a post-cannoli cocktail in the North End, hop from the Waterfront (450 Commercial Street, Boston, 617.523.0613) to the Sail Loft (80 Atlantic Avenue, Boston, 617.227.7280) to the Living Room (101 Atlantic Avenue, Boston, 617.723.5101).

Night 2: Dance — no matter how many drinks it takes you. (Our magic number? Somewhere in the vicinity of six.) Have as much liquid courage as you need, then get out there and shake it. Trust us: you’ll have a good time. Some of our favorite spots to showcase our moves include The Estate (1 Boylston Place, Boston, 617.351.7000), Avalon (15 Lansdowne Street, Boston, 617.262.2424), and Rumor (100 Warrenton Street, Boston, 617.482.6958).

Night 3: Splurge for VIP status. It may not be how you roll on a regular basis, but mingling with the pretty people behind the velvet ropes is an experience you should have at least once. The specifics vary by club and by night, but there’ll usually be a table charge, a minimum order, or some sort of mandatory bottle service that’ll get you in. If you can’t swing it on your own, gather a few friends together and split the fee — just think of it as an advance on all the free drinks you’ll score later from the moneyed VIP regulars. For the hook-up, touch base with some of Boston’s nightlife legends: 6one7 Productions (www.6one7productions.com), East Coast Clubs (www.eastcoastclubs.com), or Two35 Entertainment (www.235ent
.com).

Night 4: Host a rager. If your nightlife’s in a rut, might as well take things into your own hands, right? Get a keg of cheap beer, some bottom-of-the-line vodka, and a refrigerator’s worth of boxed wine, and host an authentic college-style soirée complete with flip-cup, beer pong, and plastic cups. Then E-vite your entire address book and prepare to party until the cops come. And this time, you’re old enough to hire a cleaning service to take care of the morning-after mess. (Dealing with the guy you wake up next to is still your problem.)

Night 5: Relive the ’80s. Even (and especially) if you weren’t old enough to party during the day-glo decade, make like it’s 1985 and spend your evening whooping it up to the sounds of Madonna, Michael Jackson, and Bon Jovi. A good number of bars and clubs host ’80s nights, but we’re loving local ’80s cover band Fast Times. They often play at the Grand Canal (57 Canal Street, Boston, 617.523.1112), Hennessy’s (25 Union Street, Boston, 617.742.2121), and Paddy O’s (33 Union Street, Boston, 617.263.7771); visit www.fasttimes.biz for a list of the band’s upcoming gigs. Bonus points if you wear something stonewashed.

Night 6: Discover your signature cocktail. It’s like your order at Starbucks — nonfat, no-foam, mocha-frappa-latte, anyone? — only much more fun. Everyone should have a signature cocktail: a drink that you order, exactly to your liking, every time you’re out. It should fit your personality and be equal parts obscure and hip. On a low-key night out, sit down with a bartender you trust, ask him or her for suggestions, and experiment. Soon enough, no one will recognize you without an [insert cocktail here] in hand.

Night 7: Participate in some bar athletics. It could be nothing more than a few raucous rounds of Photo Hunt, but you’ll be surprised what a few “drinking games” can add to your standard night out. If you’re in need of inspiration, try retro-bowling at the Milky Way (403–405 Centre Street, Jamaica Plain, 617.524.3740), hitting the pool tables at Jillian’s (145 Ipswich Street, Boston, 617.437.0300), or mounting the mechanical bull at Liquor Store (25 Boylston Place, Boston, 617.357.6800). Burning calories while you booze — what could be better?

Night 8: Participate in a wine tasting. Instead of just guzzling down glass after glass, learn a little something about what you’re drinking. Sommeliers all over the city are just waiting to enlighten you on the ins and outs of a good wine. Wine Mondays begin at 7 p.m. weekly at L’Espalier (30 Gloucester Street, Boston, 617.262.3023), while the Ashmont Grill (555 Talbot Avenue, Dorchester, 617.825.4300) hosts its Monday Night Wine Club in a more casual setting. It’s also worth checking out class schedules at the Boston Wine School (1354 Comm Ave, Boston, 617.784.7150), Gordon’s Fine Wine and Culinary Center (894 Main Street, Waltham, 781.893.1900), and Barbara Lynch’s new demonstration kitchen, Stir (102 Waltham Street, Boston, 617.423.STIR). Another option: host your own wine tasting. Ask guests to bring bottles they love, and sip away.

Night 9: Can you say karaoke? So what if it’s possibly the most cliché drinking activity out there? Nothing says “drunken good time” like belting out “Piano Man” onstage in front of a crowd of strangers. There are plenty of weekly karaoke nights; we like a venue dedicated solely to karaoke: Limelight Stage & Studios (204 Tremont Street, Boston, 617.423.0785).

Night 10: Make out in a bar bathroom. Need we say more?

Night 11: Hit a bar alone. It’s one of those things everyone should try — like solo dining, going to the movies alone, and traveling stag. Settle in with a book or magazine; grab a snack if you need something to do with your hands. Most important, be open to chatting with fellow barflies. After all, you never know who might be lingering on a neighboring stool. A few bars where we wouldn’t mind hanging out sans companions include Bricco (241 Hanover Street, Boston, 617.248.6800), No. 9 Park (9 Park Street, Boston, 617.742.9991), and the Washington Square Tavern (714 Washington Street, Brookline, 617.232.8989).

Night 12: Shots! Forgo the standard salt-tequila-lime combo in favor of more interesting concoctions. The Banderita ($7) at Masa (439 Tremont Street, Boston, 617.338.8884) is taken as a trio: a shot of tequila, a swing of lime juice, and a swallow of tomato-based sangrita. Or peruse the drink list at Eastern Standard (528 Comm Ave, Boston, 617.532.9100), where the selection of nine shots includes the Stardust and the Green Monster ($6 each).

Night 13: Pull an all-nighter. We know Boston is seriously lacking when it comes to options past 2 a.m., but do what it takes to party — literally — until the sun comes up. Once the clubs close, everybody who’s in the know heads over to Rise (306 Stuart Street, Boston, 617.423.7473) for late-night, Red Bull–fueled festivities. It’s members-only, so you’ll need to score an invite, but that shouldn’t be too difficult for a socialite like you. If you’re looking for some sustenance to get you through till morning, we recommend the South Street Diner (178 Kneeland Street, Boston, 617.350.0028) for breakfast fare, and Bova’s Bakery (134 Salem Street, Boston, 617.523.5601) for the sweeter stuff.

Night 14: Slum it. Even the prissiest of partiers has to love a dive bar every once in a while. Feel free to head out in jeans and a T-shirt, and don’t you dare order anything but beer. Our favorite holes-in-the-wall include Bukowski Tavern (50 Dalton Street, Boston, 617.267.5028), the Cantab Lounge (738 Mass Ave, Cambridge, 617.354.2685), and the Other Side Café (407 Newbury Street, Boston, 617.536.8437).

Night 15: Host a fancy cocktail party. We’re talking trays of signature martinis, passed appetizers (enlist your younger brother to play waiter), and mood music. Roof decks are ideal for these types of get-togethers, but any urban apartment will do — just dress it up with strategically placed pots of foliage and loads of candles or strings of tiny white lights. Be sure to wear something fabulous, and flit from group to group bearing conversation starters and air kisses. Pitchers of pre-mixed cocktails are key, too, along with a cabinet full of back-up booze.

Night 16: Watch the game in head-to-toe team regalia. It doesn’t matter if you’re an actual fan or just a fair-weather one; arrive in all of the Sox/Bruins/Celtics/Patriots attire you can scrounge up and be prepared to get into the game. We expect chugging every time somebody scores, not to mention obnoxious cheering and booing. After a few beers, you’ll forget that you never really understood the rules. You and your crowd will fit right in with the other die-hards at the Cask ’n Flagon (62 Brookline Avenue, Boston, 617.536.4840), Game On! (82 Lansdowne Street, Boston, 617.351.7001), the Sports Depot (353 Cambridge Street, Allston, 617.783.2300), and the Fours (166 Canal Street, Boston, 617.720.4455).

Night 17: Start drinking at brunch ...  and don’t stop until last call. We recently ran a story on great cocktail options at brunches around the city (7.31.07), so take advantage of the chance to start early. A few possibilities: the Living Room (101 Atlantic Avenue, Boston, 617.723.5101), Tremont 647 (647 Tremont Street, Boston, 617.266.4600), and East Coast Grill (1271 Cambridge Street, Cambridge, 617.491.6568). Make a smooth transition from brunch cocktails to alfresco afternoon drinks to a pre-dinner apéritif, and so on. We dare you to make it straight through to 2 a.m., no naps allowed.

Night 18: Flirt with a bartender. Why not? Worst-case scenario, you could end up with a free drink. Best case, maybe a quickie in the kitchen after-hours.

Night 19: Participate in a sing-along. Feel free to start your own on the walk back to your apartment — though your neighbors might not be impressed. Or, take part in the Friday-night piano sing-alongs — songbooks provided — that are hosted weekly at Jacob Wirth’s (31–37 Stuart Street, Boston, 617.338.8586). Also, stop in at the Black Rose (160 State Street, Boston, 617.742.2286) for nightly live Irish music that inevitably turns into a room-wide chorus.

Night 20: Fake a celebration. So what if it’s not your birthday/bachelorette party/graduation/last day of work? Pretend it is, and let everyone else in the bar join the festivities. (We have a friend who owns a fake — and massive — diamond ring for just that occasion.) Revel in the free drinks, high-fives, and congratulatory words, and let your understanding friends steal the spotlight next time. Just be sure to stick to your story: if you’re getting married tomorrow, don’t expect to “cheat” on the groom with the busboy, or the jig is up.

Night 21: Take advantage of extended salon hours. We wish we could go all Hollywood and employ a stylist to get us ready every night, but unfortunately, that’s just not possible. Many salons, however, extend their hours on certain nights to service clients with tight schedules. Arrive dressed and ready to go, then head to your nighttime destination straight from your stylist’s chair. I Soci (8 Newbury Street, Boston, 617.867.9484) is open until 8 p.m. on Wednesdays, Thursdays, and Fridays, while James Joseph Salon (30 Newbury Street, Boston, 617.266.7222) celebrates Late Night Thursdays until 9 p.m. The stylists at Shag (840 Summer Street, South Boston, 617.268.2500) can be convinced to hang around until 8 or 8:30 p.m. on Thursdays, and at Avanti (11 Newbury Street, Boston, 617.267.4027), drop by any Thursday for party music and sangria from 8 to 11 p.m.

Night 22: Do it on the roof. If you undertake this 30-day adventure before fall really sets in, you can take advantage of one of our favorite pastimes: rooftop drinking. If you lack roof access at home, we have a few suggestions: Ristorante Fiore (250 Hanover Street, Boston, 617.371.1176), the Black Rhino (21 Broad Street, Boston, 617.263.0101), the Rattlesnake (384 Boylston Street, Boston, 617.859.7772), and the Baseball Tavern (1270 Boylston Street, Boston, 617.867.6526). Too chilly? Search out the next best thing: heated patios.

Night 23: Party crash. Swathe yourself in something fabulous — there’s no way you’ll get kicked out if you’re the best-dressed person in the place — and schmooze your way in with a smile, a compliment, and, if necessary, a well-placed $20 bill. Whether it’s a corporate cocktail party or some VIP-only event, confidence is key. After all, if you can act like you belong, then you probably do. Stick to a simple story, and bow out with grace if you’re denied entrance. If you do make it inside, take full advantage of that open bar and the oh-so-inviting dance floor, and leave the crowd buzzing about the evening’s fabulous mystery guest.

Night 24: Indulge in some late-night fine-dining. Some people crave the grossest of junk foods when they’re afflicted with the drunk munchies, but we recommend taking it up a notch. A number of Boston’s most chic eateries offer late-night menus that rival anything available during the less-bleary hours. Sel de la Terre (255 State Street, Boston, 617.720.1300) serves a few choice dishes on Wednesday through Saturday evenings from 10 p.m. to 12:30 a.m. Upscale North End eatery Lucca (226 Hanover Street, Boston, 617.742.9200) offers a late-night menu until 12:30 a.m. And Miel, the “Brasserie Provençal” at the InterContinental Boston (510 Atlantic Avenue, Boston, 617.747.1000), is open for business 24 hours.

Night 25: Play designated driver (or just chaperone), and watch your friends get sloshed around you. Sounds boring, but if you plan for it, it can be as amusing as getting tipsy yourself. Just be sure to initiate a no-puking rule — and take full advantage of your hangover-free self tomorrow.

Night 26: Scorpion bowls! We don’t know what it is about a bowl full of shady alcohols and questionable juices shared (totally un-hygienically, we might add) among a group of friends, but a scorpion bowl always manages to perk up an otherwise drab night out with a little bit of kitsch. We go for the multi-strawed drinks served in fishbowls at the Landing (Long Wharf, Boston, 617.227.4321) — still open, weather-permitting — and the signature bowls from the deliciously gritty Hong Kong (65 Chatham Street, Boston, 617.227.2226; 1236 Mass Ave, Cambridge, 617.864.5311).

Night 27: Wear something out of character. Everyone has their nightlife “look,” whether it’s jeans and flats, simple black dresses, or flowy tops and heels. For one night only, change things up. Go indie-rock chick in skinny denim, or try something super-short or low-cut-down-to-there if you’re normally the conservative type. Purveyors of “disposable clothing” like H&M (100 Newbury Street, Boston, 617.859.3192), Forever 21 (South Shore Plaza, 250 Granite Street, Braintree, 781.843.2509), and, if you scour the clearance racks, Urban Outfitters (361 Newbury Street, Boston, 617.236.0088) make it easy — and affordable — to try something outside your comfort zone. You’ll feel like a new person, and who knows? Maybe it’ll become a permanent addition to your signature style.

Night 28: Become a groupie. Channel Kate Hudson and the Band-Aids in Almost Famous, then choose an up-and-coming local musician as the new object of your obsession. Arrive early to secure your front-row spot, and after the band’s set, flirt, schmooze, or buy your way backstage for a personal meet-and-greet with your new favorite. We suggest starting small at more intimate venues like the Paradise Lounge (969 Comm Ave, Boston, 617.562.8800), Johnny D’s (17 Holland Street, Somerville, 617.776.2004), or Club Passim (47 Palmer Street, Cambridge, 617.492.7679); you’ll probably have more luck, and lesser-known artists will be more appreciative of your affection.

Night 29: Buy someone (preferably attractive) a drink. It can’t hurt, right? Even if you’re attached, at least you’ll have a conversation partner for the time it takes for him or her to suck down that martini. And if you’re single? Well, the possibilities are endless. At the very least, you’ll make someone’s night.

Night 30: Start your own list of to-dos. Now that you’ve spent 29 nights trying new things, meeting new people, and visiting new places, you’ve surely amassed your own mental list of spots you’re dying to check out and events you simply must attend. Now, the next time your friends whine, “What are we doing tonight?”, you’ll have all the chic, fun answers. So what’s up for tonight? Sampling the beer menu at Deep Ellum (477 Cambridge Street, Allston, 617.787.BEER)? A pub crawl around Beacon Hill? Scamming your way past the line at Revolution Rock Bar (200 High Street, Boston, 617.261.4200)? Or all of the above, and then some ... @

[Illustration by C Smigliani]