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Tuesday, September 2, 2014 |  Madison, WI: 61.0° F  Fair
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Five first dates: If you seek love, there's more to Madison than meeting over drinks
For more photos, click gallery, above.
Credit:Sharon Vanorny

I am something of a first-date connoisseur. My last relationship ended in December of 2009, and I spent the next year alternating between "depressive hermit" and "online dating savant." In 2010, I went on 20 first dates, nine second dates, and five thirds. I don't particularly like dating, and I wouldn't say I'm good at it, but I certainly have experience.

The worst part about going on 30-plus dates in a year, aside from the crushing existential malaise, is the repetition. Coffee, a drink, coffee, a drink - after awhile, every date feels like déjà vu.

This city has so much to offer in the way of evening entertainment options - is another Brandy Old Fashioned really the best we can do? I set off to find out.

When the doorbell rang, I was bleeding. I'd cut my thumb on a bread knife and bled through half a box of comfort-flex Band-Aids.

"Hi," I said, opening the door to meet my first blind date, Sean, a bespectacled podcaster and homebrew aficionado. "Pardon the blood."

Sean was taking me to roller derby. Mad Rollin' Dolls bouts are a relatively cheap date at $10 per ticket ($12 at the door), though a beer will set you back another $5 or $6. Bouts are monthly through May and mostly take place at the Alliant Energy Center's Coliseum, 1919 Alliant Energy Center Way. (Some bouts are in Alliant's Exhibition Hall.) There are after parties, too, at various nightspots.

"Do all your first dates have to sign media waivers?" I joked as I signed paperwork at the front desk and grabbed a press pass.

"No," Sean admitted. "But I do try to have my attorney present."

We were early enough to grab seats on the floor, a row of folding chairs close enough to see the players' sweat. The crowd was thin when we arrived, but quickly reached a fever pitch of children, grannies and a man with a mohawk that required an advanced degree in structural engineering. Many fans came in costume, which made for great people watching.

By the time it was over, we'd amassed a group of eight and had long stopped following the score.

Later, Sean and I stood at my door, lit from above by the yellowish glow of my flickering porch light. "This was really fun," I said. We hesitated, smiling. Mere feet away, his friends watched from the backseat of the car. We decided to just shake hands.

My second date fell on the coldest night of the year. The flattering cut of my little black dress was wasted under layers of wool and flannel. I was meeting Matt, a quilt designer and linguistics nerd, at the Madison Museum of Contemporary Art (227 State St.) for its MMoCA Nights program, a glammed-up art opening with a DJ, drinks and a lecture. Admission is free for members and $5 for everyone else.

The exhibit, featuring work by contemporary artist Shinique Smith, was visceral and evocative. "Visceral" and "evocative" feel like naked-emperor words, the kind used by people who want to sound like they mean something without actually having to mean it, but in this case the words meant something to me.

In one piece, bits of found fabric were bundled together and hung from the ceiling, resembling not so much a hot air balloon as a child's drawing of one. Another sculpture appeared at a glance like a sad stuffed tiger, abandoned on a lonely tree stump. A third, a bundle of clothes like a runaway knapsack, was tied with a clothesline to a single high-heeled shoe, reminding me of runaway children, runaway brides and getting the hell out of Dodge.

There was a lot to talk about in the gallery itself, but when it came time for the lecture, we silenced our cell phones and our conversation, too. I'd loved the pieces in the exhibit and looked forward to the talk, but once there, I felt out of place. I grew up in a working-class family, and I'm surprised by the anti-intellectualism that stirs within me when I hear contemporary artists discuss their work. I examined my own feelings of distrust and alienation, pondering their roots. I turned to Matt to see what he thought of the lecture. He'd fallen asleep.

"Contra dance!" a friend exclaimed when I told her about my next date. "That sounds fun!" She paused. "What's contra dance?"

Contra dance is a partnered style of folk dance similar to square dancing. Madison Contra Dance Co-op meets Tuesdays at 7:30 p.m. at the Gates of Heaven Synagogue (302 E. Gorham St.). Five dollars will get you in the door.

My date for the evening was Andy, a quality assurance analyst for a local software company. We met for tacos before the dance - perhaps too heavy a meal before so much spinning. From the Square, we trudged through the snow to the dance hall.

It was narrow and bright with high ceilings and a live band on the balcony above. The group was large and varied, and most people seemed to be regulars. We arrived early, and a gregarious gentleman, the caller for the night, endeavored to teach us to dance. The results of this lesson were less than impressive.

Since we were both new and clueless, Andy and I were not permitted to dance together, instead pairing with more experienced dancers in the group. The choreography changed every 10 minutes, so just as I'd start to find my way, we'd start over with something new.

Following doesn't suit me. I'm an assertive person by nature, and I resent being led by a man. It's one of the many reasons I'm single, I suspect. My partner changed every few steps, leaving me tossed like a rag doll from one strange man to the next, hands in my face, grabbing, pushing, pulling, spinning me around. By the third dance, I was dizzy and nearly in tears.

"I feel even worse for my date," I confessed to someone who seemed to know what he was doing. "Following is hard enough. When you don't know what you're doing, it must be even harder to lead."

"There is no lead," he explained, setting me straight. "That's what I like about contra dance. No one leads and no one follows. There's just always somewhere you're supposed to be."

I am not a fan of the great outdoors. Camping, hiking, swimming in polluted lakes - I've tried to learn to love these things, but I am who I am, and who I am is inside, preferably with central heating.

Given my proclivities, or lack thereof, the next date in my lineup was an odd choice. It was a nighttime hike at the UW Arboretum, a free, guided two-mile walk through woods and wetlands, all in the dark. The low was 3, and I'd misplaced my winter boots.

My date was Mo, an engineer-turned-musician who is writing a novel about the season he spent backpacking around the country. I was in a melancholy mood. Dating depresses me more often than not, inviting comparisons to my last great love, and inspiring the special brand of loneliness that comes from being with others but feeling alone. Mo was quiet and kind, but the space between us felt like miles.

There were about 12 people in our group, more than I'd expected. We left from the visitor center on Longenecker Drive. There were two guides on our hike - one led the line, the other brought up the rear. One of our guides began the walk with a poem by Wendell Berry. She read from a scrap of paper, a dim flashlight illuminating the page as we huddled in the dark, everything silent but the shifting of boots in the snow.

To go in the dark with a light is to know the light.
To know the dark, go dark. Go without sight,
and find that the dark, too, blooms and sings,
and is traveled by dark feet and dark wings.

The trail was buried deep beneath the snow, and my boots sank with every step. The trail narrowed as we made our way across the frozen prairie, listening for coyotes or wild turkeys sleeping in the trees. We saw tracks in the snow where deer had come to eat crabapples. The sky was black as tar and the stars above us glittered like glass on a city street. It was all more beautiful than I'd imagined it could be.

We stepped out on a wooden dock, listening for the call of a great horned owl in a pond where there once were frogs. As I looked out on this frozen expanse, summer seemed like a dream. We stood still as marble, holding our breath, listening. We heard only silence.

"Why do they call?" I asked. "Is it to find a mate?"

"Most of them will have paired by now," explained one of our guides, peering into the snowy trees. "But there are a few males left, still looking for a mate. Sometimes at night you can hear them."

I listened, and heard nothing.

By the time I reached my final date, I was ready for it all to be over. For future reference, five dates in two weeks is about four dates too many. I was exhausted, and my hopes for my last date were low. I knew nothing about him except his first name: Ian.

The Wisconsin Union Directorate Film Committee shows independent, foreign and other hard-to-find films several times a week at Memorial Union, 800 Langdon St. Dinner and a movie is hardly an original idea for a date, but WUD's screenings are free, and the offerings are unique.

We met at the Rathskeller for a pre-movie beer. I'd steeled myself for an hour of small talk, then the movie, then home to my bed where I could watch The Good Wife and eat mint chocolate chip straight from the carton. But to my surprise, the conversation flowed effortlessly. I found myself laughing, relaxing, being myself. I was actually having fun.

The movie we were seeing was Catfish, a festival darling of a documentary that made me laugh, made me cry, and in one scene, made me cover my eyes with a fear I haven't felt since The Blair Witch Project.

Later, in the car, we drove for a moment in silence.

"Soooo," I said, in exaggeratedly cheerful singsong. "How was your niiiight?"

He laughed. "Actually," he said. "I had a really great date tonight."

"Well, that's a coincidence," I said. "So did I."

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