I have horrible luck with dates. The movies I suggest are straight-to-video dreck and the restaurants better suited serving their meals in doggy bags. But even when the uncontrollable variables are controlled, I still muck up the works. I’ll drink too many gin and tonics, recount the joke about the cripple drowning in the pool, or relate the afternoon I had my eyebrows waxed. Girls just don’t understand.

Consequently, I spend a good, oh, 95 percent of my time single. And since relocating to New York City several years ago, the percentage has steadily inched toward 100. In this metropolis you’re closer to pigeons than the average person. One-night stands? Please. I’m the son of a doctor of infectious diseases, petrified at the mention of STDs.

So I resorted to the unspeakable: the personals. When I envisioned the type of person utilizing personal ads, I saw a slack jawed, pockmarked mama’s boy that practiced taxidermy to unwind. Blatant exaggeration, yes, but such was my naiveté, only two years removed from college. There, it was harder to score a six-pack than a girl willing to contend with my neurotic bullshit. Woody Allen, if only the ladies found my Jewish neuroses as endearing as yours.

I voted against newspaper personals, opting for something a bit more 21^st century. Instead, I found a nice Internet dating site, centered in the aforementioned urban miasma, and whored myself. The questionnaire was basic, including about twenty questions. They ranged from my drinking preference to five items necessary for survival to favorite on-screen sex scene. I uploaded my info and waited for love to appear in my inbox.

A week after posting, a reply arrived. "Elizabeth" found my personal appealing, mostly because of my boast of "an impressive array of iron-on letters that I use to make t-shirts." I quickly replied, and a communiqué was initiated. We exchanged flirtatious e-mails for several weeks, fleshing out our faceless personalities with anecdotes and trivial facts.

Here are six things I learned about Elizabeth:

1. She was 21 years old.
2. She was from Olympia, Washington.
3. She liked horses. A lot.
4. She attended indie rock shows.
5. She embroidered sweatshirts by hand.
6. She was fixated on the South.

I, too, had visited the Northwest, enjoyed the occasional indie rock show, and wore sweatshirts. Since we were destined for each other, the next step was a face-to-face. I wrote and asked for her phone number. She gave it to me. I called.

"Hello, Elizabeth," I said like a stock car in fifth gear. "It’s Josh, the guy you’ve been e-mailing. How are you doing?"

"What? I can’t understand you," Elizabeth answered with West Coast inflection. "You sound like you’re talkin’ some sort of Puerto Rican English."

An unnecessary barb for someone enunciating like Jeff Spicoli, but I tempered my anger. I assured her I was not, and slowed my speech. We enjoyed a nice conversation, most of which centered on horses and the South. Stanley Kubrick’s The Killing had a profound impact on Elizabeth, as well as The Dukes of Hazzard. After about 45 minutes, I asked her if she wanted to do something.

She didn’t answer.

"With me," I hopefully clarified.

"Well, sure, but I don’t wanna go to another dive bar or something. Every guy I meet wants to go to a dive bar. We have to do something unique, something crazy. What do you have in mind?"

A dive bar. Cheap alcohol, lots of smoke, surly bartenders; what could be better? Pausing for a second, I recalled Elizabeth’s equine love. "You like horses, right?"

"Yes," Elizabeth said. "Why?"

"Well, how about we go to the racetrack next weekend and gamble away our rent? Maybe we’ll get lucky."

And that’s how Elizabeth and I found ourselves at the Aqueduct Racetrack. Upon meeting her, I was smitten. Standing 5’3" with short red hair and pale blue eyes and the cutest jean jacket this side of Levis, she was the prettiest person at the track. That was a compliment, though not a difficult one.

The Aqueduct was a mélange of the down ’n out, the hopeful, and the hopelessly hopeless. Mothers toting babies chain-smoked in nonsmoking areas. Grandpas watched races with fingers clutched equally around tickets and canes. Bedraggled men drank beer and rummaged through piles of discarded tickets, hoping for a winner. At least I wasn’t the only one.

The racetrack was a far remove from the metropolis, located near JFK airport. This was apropos, as the Aqueduct resembled a ’60s airport lounge for the destitute. The multi-tiered facility—painted heavily with pastels—was like an electronics store run amuck. Hundreds of banks of monitors flanked walls and hung from ceilings. They featured horse races and odds and odd bits of info. Like amoebas and their osmosis, the gamblers absorbed the flashing images.

Elizabeth grabbed my arm and pulled me close. "Dude, we are so not in Kansas anymore. Let’s bet."

I nodded slowly, duly noting the physical contact. Then I turned my attention to gambling.

The idea seemed simple enough: Step up to the barred windows, throw down a fiver, and say, "I’m betting the bank on number seven!" But betting was so, so complex. Placing and showing and tripling and exact; these terms made sense separate of the racetrack, but now I was clueless.

I scanned the board; eight nameless horses were listed, each with separate odds. Two-one, eight-five, five-three, four-two; what did they mean? I hadn’t taken math since my junior year of high school, and even then I’d needed to scrawl formulas on my hand to obtain a C in trigonometry.

"So who do you wanna bet on?" Elizabeth asked.

"Well, how about number seven?" I suggested. "Seven’s always been my lucky number."

"I like number four. And the odds are one-one," Elizabeth said. "Is that the best you can do?"

I pondered for a moment, scratching my chin and staring at the blinking and bleeping boards. Would she like me if my idea of math involved removing my shoes and socks?

"You know," I started, heading down the treacherous honesty route, "I have no idea."

"That’s all right, silly," Elizabeth giggled, tugging my jacket and squeezing my arm. "We’ll just bet a couple dollars. I just like the idea of winning."

And honesty wins again.

We stepped up to a barred bettor’s window. A white-haired granny, who looked like a Shar-Pei that had known better days, greeted us. She was wearing a turquoise Garfield sweatshirt. I’ve long felt that wearing sweatshirts in public once you’ve passed 35 is a sign that life has browbeaten you into submission. If you look like you’re ready to sweat to the oldies then, well, what do you care about?

"Whaddya two kids want?" the Garfield-lover barked in a voice thick with decades of cigarettes. My hypothesis was one step closer to theory.

"Uh, gimme two bucks on number seven," I answered. Elizabeth and I had agreed to bet on my number.

"Is that all, ya cheapskate? Don’t you wanna win big, son?"

"No thank you. That’s all for me." Son? Cheapskate? I only thought movie characters spoke like that.

"Suit yourself, ya cheapskate," the granny said. She threw my betting slip in front of me.

I squinted at the granny and snatched my slip. Rubbing the possibility between my fingertips, I shoved the paper into my pocket. Lucky number seven it was.

Elizabeth and I headed outside into the cool air and settled into plastic grandstand seats, about ten rows from the track. The grandstand was virtually vacant; most of the gamblers were inside, watching from the warmth. Joining us were a few kids chasing plentiful pigeons and a smattering of hardcore bettors. Were they hoping for a windfall or just not to fall any further?

Action soon flurried around us. John Deere tractors dragged the starting gate onto the track. Jockeys maneuvered horses into gates. Reins were grabbed tight. Horses whinnied and neighed and bucked. "Come on, number four! Johnny wants a white Christmas!" was shouted from the left. An elderly woman genuflected in front of me. Whose lucky day would this be?

I clutched my ticket and turned to Elizabeth.

She turned to me.

We smiled at each other.

And the horses took off with a shot.