Published in ReMarriage magazine in 2008

The Match Game

I was jumping back in the dating pool. So why did I feel like I was drowning?

By Timothy C. Greenleaf

Wrapped up in a combination of nervousness, anxiety, and excitement, I stood at the top of the Metro escalator and scanned the face of each woman as she stepped onto the pavement. My first date in seventeen years was due to arrive at any moment. At times, my interest was acknowledged with a friendly smile or a nervous glance away. After a few minutes, and too many women walking blithely by, I started to feel like a lost four-year-old in a grocery store.

"Are you my date?"

As the minutes unfolded, tension mounted and the wait transformed into an emotional rollercoaster ride. "Ooh! Ooh! She smiled at me! You're my date!" "Ugh... I hope you're not my date." When a vaguely familiar blonde finally appeared, we exchanged nervous glances—it was clear she was looking for someone, too.

"Andrea?"

My heart raced, but I wasn't about to reveal that I hadn't been on a date since high school.

I'd been with my college sweetheart since the second day of our freshman year in college. Though we'd grown up together throughout our twenties, we'd grown apart in our early thirties. I had thought my trajectory of life was clear. When we finally faced the situation, and decided to split, it was a seismic moment for just about everyone who knew us.

"But you got along so great!"

"It's always been Tim AND Shelly, not just Tim or Shelly."

Only one friend got it right: "It didn't seem like there was that much passion in your relationship. You never fought!"

In hindsight, that was exactly it. I don't remember the moment I realized it, but clearly my life needed adjustments. When I looked closely, I related just a bit too much to the suburban angst of American Beauty.

But now that I had turned that life inside out, and chosen to divorce, I had no idea where the "coping" path would take me. Rather than wallow in self-pity, I seized the opportunity to find what I used to dream about. I was ready to find my real soul mate.

My newfound singleness became an office project. Since I earn my living and spend much of my free time on the Internet, it seemed natural to go that route. Everyone wanted to help me write my online profile, especially after seeing my pathetic, painfully earnest first attempt. Though I tried to represent myself accurately, I found after a number of eye-popping dating experiences that truth in advertising often doesn't apply.

At first, my worst fear was that there was no one my age left. (Luckily, that clearly wasn't an issue.) But the game for me soon became figuring out why the woman who showed up was still single. What were the tragic personality flaws they couldn't overcome? Usually the lack of chemistry was immediately obvious, but on several occasions it took two or three dates to reveal the fatal fault.

But what surprised me most is that with each new date, I saw bits of myself reflected back across the dinner table. By the end of an evening, I actually started learning more about myself: what I liked, disliked, and how to be honest about what I needed to find in a potential mate.

For several months, I was dating several times a week, making absolutely no "love connections." My friends never lost enthusiasm for me, but, still, it felt like some cosmic joke where, with the TV game show music rolling in the background, I could hear Chuck Woolery cackling hysterically as each date night unfolded. Which of the 32 kazillion dimensions of eHarmony's compatibility was I ignoring? Was I trying too hard?

Fate has a way of aligning the planets and stars in ways you'll never predict. In my case, it was one five-minute window of time that changed two lives forever.

Leaving late one evening, I encountered a bewildered redhead next to the FedEx box outside my office.

"I'm Katie," she said, smiling, eyes beaming, and bobbing her head slightly. Chemistry was overwhelming and immediate. Where was that feeling in the carefully programmed, likes-and-dislikes, philosophically aligned online matchmaking? Where were these sparks with my artfully chosen, picture-driven choices?

I was late to join my friends to see Borat, but tonight that didn't matter. The several minutes we talked seemed like an hour, and we exchanged just enough information so that I could track her down later that week.

One year later, I asked her to marry me.

The joke, it turns out, is that I found what I was looking for, exactly when I wasn't looking. FedEx, in our case, delivered in ways not even we could have imagined.

Tim Greenleaf, a web producer for National Geographic, is now up to his ears in planning wedding number two. He thinks it's much more fun than finding the bride.

(Author's note: Katie and I were married on September 13, 2008.)

SIDEBAR: Top Tips for Playing the Dating Game:

1) Where is that tragic personality flaw? Does she have any friends? What happened to her last boyfriend? Any case of unsolved murder and/or restraining orders should ring alarm bells. That electronic ankle bracelet might indicate something beyond an interest in clunky plastic trinkets.

2) Is there any resemblance between her profile photo and how she looks in person? If it appears it's, say, from 10 years or 50 pounds ago (or it looks eerily like the line-up in the Post Office), you have to wonder about esteem—or other—issues, even if you like what you see.

3) Not to be vain, but does her personal appearance jive with your likes? Are you dying to ask if she just got out of bed? Are you willing to peel away the layers, as you ask yourself, "Is there actually a person behind all that makeup?" And, if she's known to her friends as "the-Hutt" in any shape or form, run away.

4) "Likes animals" on her profile might be a good thing. If that translates into owning twenty cats, and you're a dog person, you've gotta think twice. Express admiration if she mothers eight dogs, an iguana, and a menagerie of unspecified rodent-like mammals of all shapes and sizes. Don't worry: You'll find space for them in your 600-square-foot apartment.

5) Does your date seem vaguely interested in current events and/or politics? Political differences don't always doom a relationship—Mary Matalin and James Carville taught us that—but still, it's best to press buttons now rather than later. Identify her political leanings and take the opposite side: Bait her with McCain's "100 years in Iraq" comment, and she how she reacts, or dis Hillary [or Obama]'s weak war judgment, and watch how she comes to her[his] defense. Assess your blood pressure after.

6) Provoke an "anger management" reading; ask if she usually reacts this way to other guys. Make a note to have the doctor check your eardrums for damage.

7) Drooling always signifies other issues. Stay away.

8) If the raspy voice, yellow teeth, and stained fingers are sexy to you, then the smell of smoke won't bother you, either. Make sure your insurance is paid up.

9) When the check comes, be sure to ask if she can feel the chemistry between you.