by Katy Rosenberg

photos by Katy Rosenberg

If I were to put an ad in the Chicago Reader, this is what it would say:
Me: 21-year-old, single, coquettish, fearless female, straight with no potential to swing, seeks late night bar-hopping companion for friendship and shared evenings of going out without even so much as a chance of a sexual rendezvous.
You: Single, 20-30-years-old, exceptionally attractive, closeted or openly gay male to share evenings of dancing, drinking, and good times in Boys Town. I’ll be your beard if you’ll be my cover. If you’re looking for a hassle-free, non-committed, non-romantic friendship connection, and you really like boys, then I’m your girl.

Yes, a night of good music, good friends, and good fun is possible without all the usual annoyances: without that leering guy in the corner sending you drinks in hopes of taking you home; without cheesy pickup lines and pleas for digits; without inappropriate groping, rubbing, and close-talking … if, you know the right places to go. It’s all your night-out dreams come true! It surely is, ladies, a beautiful day in the gayborhood.

Dressed in a short, tan suede skirt, stilettos and a sexy, black gauzy shirt, I set out for Harry’s Velvet Room to celebrate a friend’s birthday. A dim, urban, romantic locale in the Near North neighborhood, this lounge is one of those places to see and be seen from the seated comfort of a plush booth amongst friends. We were an attractive crowd, and it was certain to be a night of expensive drinks, scintillating conversation, and urban excess. I was by no means on the prowl, nor was I hoping to be approached; I simply wanted to go out and enjoy the company of friends at a swanky club as a single, independent woman.

An hour later the birthday girl succumbed to her seventh birthday martini and the party dissipated. My best friend and I were out the $15 cover and suffering from a severe lack of fun and meaningful engagement. I downed the drink that had been sent my way by a smooth-talking charmer earlier in the night, and given the fact that we were simply too dressed up to go home, we decided to seek out new bars downtown. My semi-closeted friend decided tonight was the night to explore the Gay-Chicago scene for the first time. Arm in arm, this ambiguously straight couple set out for Boys Town.

Technically called Lakeview, Boys Town refers to the area surrounding North Halsted Street, contained by Belmont to the south and Irving Park to the north. It extends peripherally east to Broadway Street and west to Clark Street, with a few choice bars scattered a bit further. If you’ve ever taken the Red Line to Belmont, you’ve been to Boys Town without even knowing it.

Entering from the southern end, you’ll find the dance club Spin at the corner of Belmont and Halsted. Moving north on Halsted you’ll hit Gentry, Felt, Sidetrack, Roscoe’s Tavern, Cocktail, Buck’s, Voltaire’s, and the ever popular, aptly named Manhole. In a short six-block radius you have access to taverns, sports bars, dance clubs, lounges … really any kind of bar you could imagine. And there’s rarely a cover.

On this first adventure into Gay-Chicago my friend and I headed straight to Roscoe’s Tavern, one of the most well-known gay bars in Chicago, replete with pool table, dance floor, and six functional bars. As we entered the bar, my friend clung tightly to me – he was nervous and excited, and not necessarily comfortable with the level of openness Roscoe’s required of him. It was a costume night and the bouncer jokingly asked if we were dressed as a straight couple. My friend smiled, held me tighter, and replied, “It’s no costume.”

One beer later, however, he was off perusing the bar and I found myself boyfriend-less, dressed to the nines, and alone in a bar. I spent three and a half hours sitting on a bar stool while my friend made his rounds. And I don’t think I spent more than a five-minute interval by myself. Over the course of the night I met three types of guys: the Lonely Guy, the Bored Guy, and the Intrigued Guy.

Lonely Guys:

Honestly, there were more disregarded men in this bar than I had ever seen out before. They had come alone – a more common practice in Boys Town than in most parts of the city – or had unfortunately found themselves alone. Their most common opening line: “What’s a pretty girl like you doing sitting alone at the bar? Do you mind if I join you?” Wow. At separate times both Chad and Bob, two of the lonely guys, offered to buy me a drink. I always accepted, knowing that there was no ulterior motive. When was the last time you had a sincere, ten-minute conversation with a guy who bought you a drink?

Bored Guys:

The bored guy, Jeffrey, was aloof and cool. Dressed in a polo shirt over a white t-shirt and jeans, he was cute in an Abercrombie and Fitch kind of way. He made his approach resignedly and asked to bum a smoke. He explained to me that there was no one worth talking to that night, and he just wanted to finish his beer and then leave. Then he looked me up and down and said, “You queens are better than you used to be. You look like a real girl.” Ummm, that’s because I AM a real girl! And thank you for noticing. We had a little laugh about that, and the lightened mood opened up a great conversation about sexuality and attraction. Half an hour passed before Jeffrey remembered he wanted to go home.

Intrigued Guys:

Unlike Jeffrey, Miguel and Peter found me to be the most intriguing person in the bar. They couldn’t figure out what I was doing there all alone, or how I got my hair so straight. And also, what brand of makeup was I wearing? Who did I think was the cutest boy in the bar? And did I want to do a shot? The answers: “MAC, still undecided, and hell yes.” And, after I dished out all my girly secrets, I explained that I wasn’t actually alone, pointing out my best friend across the bar. If I was an interesting specimen before, after seeing my friend, these boys were prepared to perch next to me all night. “He is soooooo cute!” I closed out my night with Miguel and Peter talking about school, traveling, love. We laughed until it hurt. Would we, I wonder, ever in a million years have met at a straight bar?

The rest of Roscoe’s that night seemed entirely disinterested in the girl at the bar. They were out with their friends, looking to meet a potential love-interest, getting too drunk to pay attention. Pretty much the same crowd as at any bar on any night in any city. The difference is that I didn’t feel like prey. Sitting alone was a socially acceptable, safe course of action and led me to some of the most interesting bar talk I’ve ever experienced.

Since that first fateful night, Boys Town has become one of my favorite late-night destinations. For those nights when you just want to have a few cocktails and dance, or meet interesting people without the unspoken contingency of “maybe I can take her home tonight,” the gayborhood is the place to be. We’ve done the circuit of bars up and down Halsted in the last few weeks. So here’s my own personal Zagats guide on how to do it up right in Boys Town:

Rosenberg’s Chicago: A Straight Girl’s Guide to Boys Town

Berlin (954 W. Belmont St.): According to most who know, “Berlin is where the freaks hang out.” This is where you’ll catch an eyeful of leather, queens, transvestites, and the like. Drag races and cage dancing make this an interesting place for some good old-fashioned “freak watching,” but it’s not, per se, the coolest place to chill. House, trance and general club music are often the tunes of choice, with little opportunity for idle chatting. Drinks are also overpriced and minimally alcoholic, but it is still a fun place to check out, especially because you know you’ll never feel like the Cousin Itt of the group. Straight Girl Rating:

Charlie’s (3726 N. Halsted St.): A country-western dance hall by day and gay dance club by night, Charlie’s is a great choice for after hours. Tire yourself out on the massive dance floor to mostly Top 40 and 80’s tunes. It’s open until 4 a.m. on Thursdays and 5 a.m. on Fridays and Saturdays. A relatively mixed crowd, average priced drinks and good dancing fun! Straight Girl Rating:

Cocktail (3359 N. Halsted St.): Men in G-strings and work boots dancing on stage, dollar bills floating through the air, screeching, hollering … we must have made a wrong turn into a strip club. But no, the drag-queen bouncer explains to me it’s just Cocktail on a Thursday night. Right. A bit on the skeezy side, this small mid-Halsted bar caters to an older, mostly male crowd with a few queens and a smattering of lesbians. While the strip show was a little on the intense side, it did make for great small-talk. Basically, Cocktail is kinda like the Cheers bar, only gayer. On a non-strip night it’s a nice place to meet some older folk. And, there’s never a cover. So if you take it off, so will Norm! Straight Girl Rating:

Felt (3342 N. Halsted St.): Catering to a young, very attractive crowd, this small, trendy martini lounge is the most straight-friendly bar in Boys Town. Bartender Blair told me that the management is trying to “mix up the scene” by enticing more women to hang out at the orange, light-box bar. That means your first shot is always free. Throw in great promotions like the “very chill” San Francisco house-music Mondays (replete with candles, flowers and dim lighting), and you’re guaranteed a hip evening in chic company. Specialty martinis are the drink du jour. The key lime pie martini tastes like a little bit of heaven, or for you hardasses out there, the dirty martini with two olives is totally hot. Straight Girl Rating:

Gentry (3320 N. Halsted St.): Something of a Cabaret bar, Gentry features open mic night on Tuesday with a musical theater twist. If The Sound of Music is your bag, then this is your place (because you are obviously gay). You’ll be in friendly, approachable, cheery company and the music is one step above karaoke. Straight Girl Rating:

Manhole (3458 N. Halsted St.): This dark, cavernous watering hole with low ceilings left me feeling very dirty. And it wasn’t just the inescapable screening of hardcore gay porn in every corner of the bar (also totally hot). By 1:30 a.m., there were fewer than 10 people, all men, all sitting closely in pairs. The exclusively straight management knows their clientele and gives them “what they’re looking for.” The bartender regaled me with stories of bathroom orgies and swingers while my friend made some undesirable friends of his own. I don’t think Manhole has seen a woman who wasn’t part of a swinging couple on the hunt in years, thus making me feel quite out of place. This is the one bar I cannot in good faith recommend. If, however, you’re into watching hardcore ass sex on big screens, maybe your hole belongs there. Straight Girl Rating:

Roscoe’s Tavern (3356 N. Halsted St.): Roscoe’s is the “assorted flavor” Jelly Belly of Boys Town. You can find anything you’re looking for on any given night. You can try any one of their six bars on for size, plus a beer garden for Chicago’s two months of good weather (okay, three weeks, tops). For karaoke, Tuesday is your night. And on Fridays the dance floor hops until 3 a.m. (it’s 2 a.m. all other nights when the scene is a little more like the neighborhood bar/pool hall). The crowd is friendly, diverse and out for a good time. Last call does tend to be a little meat-markety, but the place has so much character, it’s worth enduring the five uncomfortable minutes of sitting alone while everyone else finds a bed buddy for the night. Straight Girl Rating:

Sidetrack (3349 N. Halsted St.): Sidetrack may just be the coolest theme bar in Chicago. A self-proclaimed video bar, this expansive, modern oasis shows movies in the front room on a big-screen TV, and in the back, small screens play SNL clips and Monty Python (sorry, no gay porn). South Beach it ain’t, but the specialty slushies (SoCo Hurricane, Midori Melonball, Ketel One Krush, Smirnoff Pink Lemonade…delicious!) and tropical theme help ease the winter blues. A sophisticated, interesting crowd of eye-candy made my visit more than pleasant, and the women’s bathroom is pristine! This is the perfect place to grab a Vita Pup and watch some tube (no, not lube). Straight Girl Rating:

Spin (800 W. Belmont St.): At the corner of Belmont and Halsted, Spin eases you gently into Boys Town. A low-key, unpretentious club, Spin always caters to the mixed crowd that calls this bar home. The front room provides the necessities—large square bar bordered by pool table. Just behind, you’ll find the dance room where DJ’s spin those funky club beats all weekend long. This locale is full more often than not, although people tend to come with friends and stick with friends. Not the place to meet new folks. Straight Girl Rating:

Katy Rosenberg is neither gay nor Jewish ... discuss amongst yourselves. Or discuss it with her, k-rosenberg2@northwestern.edu.

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