As luck would have it, I bagged myself a girlfriend who lives not in a lesser borough, above 14th Street or even anywhere in the vicinity of the tri-state area. Nope. I'm the champ who scored that special someone who lives 1,000 miles away, in Chicago, Ill., a place best known for wind, Barack Obama and pizza riddled with too much cheese.

After spending a week together in the depths of rural Michigan for the hugely gay Michigan Womyn’s Music Festival, we drove to her hometown. The festival was fun and all, but it felt good to be back in a city. Still reeling in the after-effects of convos about Artemis, Reiki and chakras, daily viewings of The Vagina Monologues and the gruesome repercussions of a low-sodium vegan diet (i.e. being hungry for a week), the grimy smells and clanktastic sounds of a major city were as refreshing as the feather-floaty vocals on that Seals and Croft track, “Summer Breeze.”

A die-hard cynic I’m not, but if I don’t hear at least one bitter rant or skull-piercing siren a day, I feel empty inside. The intangibly seductive air that raw-dog cityscape provides and the glass-is-half-empty outlook that my family and friends embrace was such an integral part of my upbringing that anything outside of city life gets old and uncomfortable for me, fast. So when her car pulled into the city from the crunchy festival, I sighed a sigh of gargantuan proportions. Ah. Life as it was meant to be lived, I thought, taking in the millions of blinding tangerine lights on the city’s skyline, Chi-town's inhabitants congregating in sweaty clusters on gum- and cigarette-strewn streetcorners and stoops.

"Let’s go out tonight,” my girl suggested after parking her car in one of Chicago's famous back alleys near a large toilet-paper sculpture of a pumpkin head propped up against a dumpster.

“Oh my God, yes,” I replied, envisioning the line-up of dirty Martinis I’d surely pound and the cacophony of jaded folk in whose company I’d surely pound them. So she put a call into a friend, who got us on the list of some fancy club where Samantha Ronson was spinning. I weaseled myself into a tiny dress, she put on a dress shirt, we met up with some of her friends and moseyed on into the spot. We were the only dykes there. The place was crawling with tan, blazer-clad, middle-aged men jonesing for the eldest Lohan sister. Underage models the width of corn-silk strands hobbling around in heels gawked at Lindsay and the sallow lesbo in headphones standing before her, the curious creature who turned the former Disney queen into a blithering gayass. I watched as a wide variety of straight white people attempting to appear uninhibited ordered Red Bull vodkas while dancing frantically against each other’s behinds, eyes on the paparazzi fodder "canoodling" in the DJ booth all the while.

Here's a way to feel poor and fat: plant your ass just inches away from the wormiest, wealthiest and perhaps most ubiquitous lesbian couple in media history. They may be the spitting image of Ursula's creepy eel gimps Flotsam and Jetsum in The Little Mermaid, and they may collectively have been a part of zero noteworthy professional endeavors (Mean Girls, of course, notwithstanding.), but they sure are thin. And rich. And in a drunken stupor, with my dress hiked up over my ass (It was too tight.), weave scraggled into an accidental beehive while sloshing vodka all over my tits, I may have tried to convince Lindsay's bodyguard to step aside so that I could teach her a thing or two about the joys of femme pride. (Lindsay was trying to rock some weird headband, Hairspray heroine Tracy Turnblad-style; like "fetch," it just wasn't happening. S-Ro wore a knee-length white hoodie, looking like a scrawny kid in a Halloween ghost costume. Also, a futchy Klansman.) The bodyguard said Lohan was "shy," so I should beat it. I stood there wondering if I could afford another drink. At places like that, the answer more often than not is no.

The night ended with me swimming in a family-sized platter of wings just minutes before dedicating Keith Sweat's "Twisted" to my girlfriend at a low-end karaoke bar downtown. I was terrible. "You were great," she said.

Funny how the best nights always start out strange. In the car ride back to her place, Kanye's chart-topping ode to the city came on the radio. "Reach for the stars so if you fall you land on a cloud. Jump in the crowd, spark your lighters, wave 'em around. And if you don't know by now, I'm talking about Chi-town."

I looked at my love and held her free hand as she drove. Feeling inspired, invigorated and at peace, thinking about how good it feels to care, I realized that the side of her face against the night looked like home.