[nightlife2008] 
131 DARTMOUTH ST., BACK BAY, BOSTON. 617.859.8886. DOUZOSUSHI.COM
I don't feel like a grown-up yet. Grown-ups go out downtown on purpose, drinking martinis, wearing long coats and talking about friends' impending homewreckages. So, for me, drinking at sleek, modern Back Bay sushi restaurant Douzo was like playing dress-up. Wasted.
[nightlife2008] 
1254 BOYLSTON ST., FENWAY, BOSTON. 617.536.1950. NIGHTCLUBMACHINE.COM
Citysearch cites Machine as "the Boston bar for gay men who want other options than just dancing and drinking," and, while I am neither gay nor a man, I too love options when it comes to a night out. Located on Boylston Street right by Fenway, Machine really does have it all: four bars, billiards, arcade games, dancing, a super friendly staff and an activity called "Feeding the Bears," which I am told involves hand-feeding a burly man who is locked in a cage.
[nightlife2008] 
58 JFK ST., HARVARD SQ., CAMBRIDGE. 617.864.9161
With its mix of the balding, the pierced and the confused ("So ... why can't I have a margarita?"), Shay's Pub and Wine Bar is so low-key that even the Harvard grad students blend in. A tiny and vaguely English walk-down on JFK Street., Shay's boasts a lovely outdoor patio, a prime people-watching spot in summertime and a base for smokers to huddle for warmth and secondhand in the winters.
[nightlife2008] 
525 TREMONT ST., SOUTH END, BOSTON. 617.338.5338. SIBLINGRIVALRYBOSTON.COM
I find Matthew Lishansky, director of operations at UpStairs on the Square, at the bar welcoming my rain-soaked ass with a hug and kiss. "I've never been here before, but my friend Jess used to be the pastry chef, and begged me to come," he says, dipping into a bowl of wasabi-coated peas.
[nightlife2008] 
250 HUNTINGTON AVE., BOSTON. 617.424.1950. BETTYSWOKANDNOODLE.COM
The discrete splashes of crimson on the menu, carpet and napkins (along with the indiscriminately infused '50s and Asian motifs) compose a posh ambiance that hints at a blow to the wallet. But since the Dig's buying, I plop down onto a mock-diner barstool and scan the drink list.
[nightlife2008] 
711 CENTRE ST., JAMAICA PLAIN. 617.522.9500. CAFEDBOSTON.COM
Despite living within a stone's throw of Café D for three years, I never made it in. The dark windows and thick front curtains hid whatever shenanigans took place inside. I never saw anyone go in or come out, and I assumed the place was a secret drinking society for the swanky-clothed, disposable income types.
[nightlife2008] 
280 GREEN ST., CENTRAL SQ., CAMBRIDGE. 617.876.1655. GREENSTREETGRILL.COM
I didn't know exactly why I was going to Green Street Grill, an establishment known for their extensive list of perfectly prepared cocktails, with Eastern Standard Kitchen's talented sommelier, Erin O'Shea. It was her choice—perhaps after studying, sipping and talking about wine all day she was looking to mix things up?
[nightlife2008] 
215 CHARLES ST., BEACON HILL, 617.224.4004. LIBERTYHOTEL.COM
I discover that Saturday night at the trendiest, velvet-roped spot in the city is a serious zoo. Thankfully, some media maneuvering allowed my crew to bypass the frustrated mob waiting in the painful, hair-gel-freezing cold.
[nightlife2008] 
840 DOT. AVE, DORCHESTER. 617.288.6288
A patron I'll christen The Historian tells me 650,000 people have written about the Dot, including Steven Spielberg. I am dubious. Alchemist Lounge bartender Carrie Hirshberg picked this place for her encore Five Drink cameo. [We visited the Alchemist last fall.—Ed.] The Dot's a humble, utilitarian joint she affectionately calls a dive.
[nightlife2008] 
234 BERKELEY ST., BOSTON. 617.266.4680. BOSTONPUBLICMEAT.COM
Since Boston Public is in the Louis Boston building, and all I know of the place is that it's ragingly expensive, I call to find out if there is a dress code—like, no sneakers or something. The guy on the other end of the phone says: "Just think like a celebrity." I tell him that I'm serious and want to know if I'll be turned away for one reason or another, and he reiterates verbatim, "Think like a celebrity and you'll be fine." Oh shit is what I'm thinking, but I head over in a tie anyhow.
[nightlife2008] 
40 EDWIN LAND BLVD., CAMBRIDGE. 617.497.4200. RESTAURANTDANTE.COM
Despite that Dante sits in the shadow of the CambridgeSide Galleria, it acts like—and could very well be—a Michelin star-ownin' hotspot. Chef Dante de Magistris and his staff mixologist, Stephen Shellenberger, have enough experimental chops to match their East Cambridge scientific brethren. This week, they tested out a few of their secret recipes on me and my stylish companion, Darryl Settles, a founding partner of The Beehive in the South End.
[nightlife2008] 
134 SMITH ST., MISSION HILL, BOSTON. 617.566.6651
Of all the things I thought I might encounter at the Squealing Pig, a Bostonian who's never heard of Whitey Bulger wasn't one of them. But I'm getting ahead of myself. Lolling in the mud pit of Mission Hill, the Pig is a cozy-yet-spacious refuge against the hellish March winds. A sprawling beer selection, rhapsodically good pub grub and down-to-earth clientele make this the perfect spot for a midweek sloshfest.
[nightlife2008] 
1 KENDALL SQ., CAMBRIDGE. 617.494.1994. CAMBREW.COM
I find that the best time of day to start imbibing is five minutes before noon. As that good angel on your left shoulder starts defending the decision, "Hey, it's technically lunchtime, it's cool to have a drink or two," the bad angel on the other quickly applauds the heretical move spouting, "Fuckin' A-right, man ... a morning beer!" With amazing food and a menu of diverse beer styles, the Cambridge Brewing Company is the place to enjoy a liquid-nooner with some friends—and in this case, the world-famous BeerAdvocate brothers, Jason and Todd Alström. Respect!
[nightlife2008] 
249 PEARL ST., SOMERVILLE. 617.628.6525
The Paddock is the epitome of a neighborhood restaurant, and its familial warmth resonates from its kitschy equine décor to bartender Tony's banter with the regulars. "What can I get for you kids?" is how he greets everyone from 60-year-old ladies to twentysomething couples. They've reopened under new management at the beginning of the year with the old chef, Michael, taking the helm as owner. Overall, it's a nice place for a low-key evening out or to watch a game with reliable locals.
[nightlife2008] 
92 HAMPSHIRE ST., CAMBRIDGE. 617.354.0766 BSIDELOUNGE.COM
To the drinking novice, the B-Side Lounge could be very intimidating: The permanent martini coolers dripping with condensation, the stacked drink menu listed in order of liquor type and the well-kept yet scruffy crowd. Thankfully, I am a drinking novice like the sky is a neon yellow-green. This was going to be fun. Bartender Dave, who some say is the greatest in town, welcomed me with his glowing smile and shirt sleeves rolled up to reveal tattooed arms. My friends had yet to arrive, so I took a seat at the back end of the bar and he handed me the drink menu as if it were Holy Bible—which, to him, it kinda is.
[nightlife2008] 
477 CAMBRIDGE ST., ALLSTON. 617.787.BEER. DEEPELLUM-BOSTON.COM
The prospect of drinking with Lauren Clark, booze journalist (check out drinkboston.com) and walking alcohol encyclopedia, is daunting. It feels like a blind date: meeting, drinking until things get pleasantly fuzzy and hoping to glean some of a stranger's philosophies. As I wait, the bartenders keep checking in with me. Later, Clark tells me that's one reason Deep Ellum is among her favorite bars: "The staff are laidback, but offer good service. And make good drinks. The owners, Max [Toste] and Aaron [Sanders], educate the staff. They want them to be very knowledgeable."
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