Serendipity and the Single Girl

Law Firm 10 Columns, Law Firm 10, Lawyer

Christopher Columbus was searching for a new route to India and instead happened upon the Americas. This past weekend, I was angling for a posh, Ivy League alum and instead found myself waking up next to a snoring Hoosier. I hope the analogy proves accurate.

One of my law school girlfriends got married this past Saturday. Much of my selfish pre-wedding excitement resulted from the fact that she and her fiancé both went to Yale undergrad—ensuring a good crop of eligible bachelors. My recent Chicago Marathon training also solidified that I’d look good in my cocktail dress, and the roster included a JFK Jr. look-alike (who made a bundle at Goldman, cashed out, and settled into a carefree life in Aspen long before the economic volcano erupted) on whom I’ve nursed a crush for three years. Clever scheming led to my placement next to JFK Jr. on the reception seating chart.

Ah, the best laid plans.

In an act of total disregard for my obsessively controlling tendencies, the seating chart was ignored. JFK Jr. took a seat at the other end of the table next to his sister (WTF?). I ended up wedged between a married guy and a rather stocky friend of the bride’s from high school who everyone referred to exclusively by his one-syllable German surname.

Despite my huff, by my third forkful of salad, I discovered that “Schultz” was actually really easy to talk to. We were both Ohio expats living in Chicago, and I sensed he was impressed that I could hold my own discussing the potential of the Bengals’ recent acquisitions.

I tallied Schultz’s pre-requisites during the main course. He (i) has been employed by Toyota for the past eight years (and, thankfully, not at a dealership); (ii) is a homeowner; (iii) is currently single; and (iv) owns his own tuxedo and manual bow-tie. The conversation eased along seamlessly—helped out, no doubt, by steadily flowing Grey Goose & sodas—and I felt comfortable enough by the meal’s end to not only have my cake, but to eat his too.

My aforementioned training schedule forced me to run 10 miles that morning, and I hadn’t realized the TKO effect an open bar would have on me after such a dehydrating workout. Which is my ladylike way of explaining that I have no recollection of the remainder of the reception. Though I think at some point Schultz may have done the worm, it certainly doesn’t justify waking up Sunday morning from a nightmare featuring a ferociously growling lion and realizing that the sound was actually Schultz’s snoring.

I instinctively looked down—my dress was still on. Either he was a gentleman or drunker than I was.

I Google mapped myself on my Blackberry to discover I was in Irving Park—a little farther north than I would have expected from an auto exec with his own tux. The bedroom itself was too dark to analyze (though I discerned the form of some rather troubling Dry-fit polos and pleated pants piled on top of a hamper), so I decided to investigate while getting a desperately needed drink of water.

What I saw next kicked my hyper-analytical lawyerly pessimism intro overdrive. The living room walls were painted a garish shade of red—Hoosier red, apparently, given the abundance of Indiana University paraphernalia cluttering the walls and grimy shelves.  I noticed an aging foosball table near the entrance to the kitchen. I didn’t understand its significance (i.e. its presence had foreclosed the possibility of a dining table) until I saw the dirty snack tables placed strategically in front of the two full-size couches, littered with evidence of last night’s post-reception Five Faces drunken feeding frenzy.

The focal point of the living room was clearly the 60-inch TV proudly displayed on a dust-covered entertainment console from Ikea.  To its right was a dueling 50-inch TV atop an old bedside table—and a Wii and Guitar Hero instrument littered around indicated that the guys who gather in Schultz’s mancave to satisfy their primitive appetites simultaneously play NBA Live 09 while watching the NBA playoffs on the bigger TV.

Snoring from one of the other bedroom doors off of the living room indicated the presence of another man, possibly a roommate.  I tripped over a massive formation of poker chips and a giant piggy bank in the shape of a guitar adorned with a photo of fat Elvis on my way into the kitchen.

I opened one of the kitchen cabinets hoping to find a glass but instead saw a hammer, two screwdrivers, several different grilling spice rubs, four Toyota travel mugs and one of those animatronic singing Big Mouth Billy Bass toys that were popular in 2001. In the next cabinet, I carefully selected the cleanest-looking plastic cup from a collection of mementos from various 1999 frat parties. Despite the existence of a dishwasher, the sink was piled high with dirty dishes. And I aborted the water-drinking mission.

Lest I end up tricked like Goldie Hawn in Overboard into dusting poker chips and wading through mountains of crusty dishes from a tribe of primitives led by Schultz, I snuck into his bedroom, snatched up my Miu Miu heels and hightailed it.

Once back inside the safety of my high-rise apartment in River North, I settled into my Sunday routine—which means I spent the rest of the day fighting the rising tide of depression in anticipation of another week. The D.C. partner I work for on a local case treated me to an hour’s worth of cross-examination via email on the status of witness interview summaries and deposition outlines that I owed him. Totally deflated, I called three friends to re-cap the prior night but only got their voicemails.

Monday morning, I settled in bright and early to finish up D.C. partner’s summaries and outlines. In the throes of misery, my mind drifted back to Saturday night. Schultz exhibited a fair amount of potential (from what I could recall). Should I have tiptoed back into his den of apneatic slumber, changed into one of the XL-sized Bengals t-shirts strewn about the room, and climbed back into his headboard-less bed? Finding out if we get along over breakfast as well as we did at the reception under the influence of countless drinks would clearly have been a more enjoyable Sunday.

Suddenly I was overwhelmed with pangs of regret. The same obsessiveness that backfired and happily landed me next to Schultz instead of the sister-loving JFK Jr. was the same obsessiveness that forced me to flee the scene. In his bachelor pad devoid of feminine influence, I let judgment get the better of me and ran past the opportunity to connect with a potentially good, real, honest man in order to seek refuge in my safe, shabby chic loneliness that’s grown all too familiar. And there, at 10:30 on a Monday morning, I had a wake-up call.

So I did what I do best (i.e. abuse the privileges of Westlaw access) and located the public record that proved Schultz is, in fact, the owner of his pad and revealed his phone number. Although I had been given a fleeting chance to observe his unadulterated, natural habitat as well as preview what kind of project it would be to sand down his rough edges (not to mention improve the fair-market value of his condo), I actually got along with him.

Now I sit, billing wasted hours. Obsessing again. Waiting for a response to (hopefully) the wittiest voicemail message I have ever mustered. Except it’s on his home machine. And with my luck, the snoring lug from the other room will erase it before Schultz ever gets to hear my hopeful message to reconnect.

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