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It was like an exotic Barbie carpool.

I was hanging out with my hairstylist, Eve, for the first time and as we drove from condo to condo to pick up her friends before heading into nearby Chicago, I was struck by the fact that each of these multicultural women was more beautiful than the one before. As I was introduced to each, I began to understand part of their secret. One was a hair colorist, another a makeup artist, and another a hairstylist. We were like a day spa on wheels.

As my stylist told me about all the procedures they swap with one another—hair cuts, highlights, waxing, massages, manicures—I began to feel like the greying, unwaxed stepsister of this little Friday night outing.

I'd been delighted when Eve, a fellow believer singleton, had invited me to join her and her friends for a special event at Chicago's Museum of Contemporary Art. She thought it sounded like a "classier" option for trying to meet eligible men. Wanting to connect with Eve and to try a new adventure, I said yes.

So here we were, art- and people-watching at the MCA. Since the admission fee included access to the whole museum, we started out by meandering the halls of funky artwork. The large number of black-clad city-folk in the small space made it warm, but my coat was the funkiest part of my outfit, so I kept it on. I was hot but hip.

Eve and company and I stared in confusion at mobiles, sculptures, paintings, and collages, occasionally sharing giggles at the absurdity of a piece. I was most entertained by the captions accompanying each one—explaining the significance of the use of red or the statement the artist was making by including the doll's head. Mmmm, sure. It all seemed to me like a great high school English assignment. "OK class, here's a piece of art. In 250 words I want you to concoct its meaning."

I was all a-smirk until I got to an odd orange piece that looked like a modern confessional. Or an empty storefront. Or something. But when I read the caption, something rang a bell. "Hey, I think this was done by that couple who did The Gates in Central Park last year," I said to Haircolorist Barbie. Blank stare. "You know, that funky eastern European couple who put those big orange gates all over Central Park after years of trying to get permission," I continued, hoping to ring a bell with one of our crew. "And I think they also covered a whole island in fabric somewhere. And all the sidewalks in this one section of Kansas City with pink material." Now they all stared at me like I had five heads. What was I blathering on about? And, more importantly, why did I care?

Eh, I finally figured, they have their thing—looking fabulous—and I have mine. Sure, theirs turns heads and get them dates and mine simply makes me a half-decent Trivial Pursuit partner, but I guess we all have to excel at something.

A few rooms later I stood in front of a light-box looking structure and finally thought, I think I get this one. It was a picture of a poor man from a Third World country lit up electronically. His face appeared twice—up high on the wall and down low by the floor. The placard next to it mentioned something about the juxtaposition of the electricity and the person from the Third World, and the perspective of the viewer either looking up to or down on the face affecting our perception of the man. It was intriguing. I didn't want to hang it in my living room, but I liked it.

Once we'd seen all the artwork, we wended our way to the food and bar area. The people watching was excellent. There were a few mysteriously tan men (obviously not brought on by the January sun in Chicago) and a few men who looked like extras from Beauty and the Geek. One kept wandering about with two glasses of wine held aloft obviously looking for someone to give one to, and I kept trying to avoid his gaze a) because I didn't really feel like a drink and b) because I was afraid that Ashton Kutcher and a reality TV camera would suddenly appear from behind the tray of mini-eggrolls.