Everyone always asks me why I’m so pessimistic. To the casual outside observer, I’ve got no reason to pervasively expect the worst in all situations. But if you spent a day or two trudging around in my Christian Louboutin hidden platform pumps, you might understand why my glass (even when it contains a Wine Spectator-lauded 2003 Brunello di Montalcino) is perpetually half empty.
In case you haven’t already guessed, I went on my first date with my co-worker Carson. And it couldn’t have gone better. In fact, it went so well that we even went on a second date—on New Year’s Day, no less.
On both dates, my hair cooperated (it is a rare occurrence when I’m able to keep my hair down for an entire evening, and the likelihood of being able to keep it down for the duration of TWO consecutive dates occurs with the same frequency as a galactic equinox), I didn’t feel fat, and I was able to pick out absolutely perfect outfits. You know, the kind where I was somehow able to appear effortlessly, casually sexy with just the right mix of trendy and elegant. But not at all high-maintenance.
Even better, the chances of anyone at the firm getting suspicious is at an all-time low. I have the non-equity litigation partner whose wife kicked him out of the house on Christmas Eve after discovering evidence of an extramarital affair with his young associate protégée to thank for that. His secretary, who made him a reservation at a local hotel and who has been fielding phone interrogations from the jilted wife since the Monday after Christmas, has promised that the saga will be long and dirty—and she will be reporting all of the morbid details directly from within the trenches. Carson and I could easily fly under the radar for the entirety of 2010.
Put simply, Carson is hilarious, smart, kind, and thoughtful. In fact, by the end of the first date, we were already having conversations about Things That Matter. In other words, I was paying attention and interested in the things that were coming out of his mouth. When I got home that night—after he insisted on the cab dropping me off first, even though it was out of his way—I called my mom in the middle of the night to tell her that I’d found the guy I was going to marry.
Our second date was equally flawless. We had our first real kiss, which was absolute perfection. Then we slept at his place and fooled around enough to keep it interesting but not so much as to destroy the sanctity of the obviously progressing Relationship.
I awoke the following morning in his Percale sheeting to the smell of brewing Dunkin Donuts coffee. (I swear to you—and my condolences to the residents of California—best coffee on the freaking planet.) He had apparently purchased some especially for me after listening to me rave about it on Date #1. When I wandered into the kitchen, I found the table set for breakfast.
At this point, it’s more than fair to stop me and scream, “What could you POSSIBLY have to complain about?!” But please be patient. I’m about to explain why my white porcelain Apilco coffee mug was only half full.
Over my first breakfast of 2010 (not to mention my first breakfast with a guy in two years), Carson cleared his throat, stammered a bit, and revealed to me that he is DIVORCED. And has a CHILD.
Well, it at least explained the photos of an adorable dark-haired girl that I briefly caught sight of when being whisked through his place in a semi-drunken frenzy the night before. He apologized for not bringing it up during our first date, or before or during the second date. He explained that he feels awkward and ashamed about it—not to mention, it’s hard to work a sob story about a failed post-college shotgun marriage that unraveled during law school into otherwise upbeat conversation.
Personally, I thought he was playing dirty and trying to get me hooked before throwing out the ultimate red flag/deal-breaker combo. Which is precisely what happened, because if he had dropped this particular bomb sometime prior to me falling prematurely (but conclusively) in love with him, I would have cut and run immediately. But at this point, I’m thoroughly intoxicated by the otherwise sublimity of what’s been unfolding ever since our fateful chance meeting at the Bengals bar.
It also occurred to me that the fact that he’s a relatively recent lateral who practices in a totally different group separated from me by three whole floors (a fact I had initially celebrated because it would insulate us from the nasty side of intra-firm romance scrutiny) was precisely to blame for my ignorance on his previously married-with-child status.
Which brings me back to my TOTALLY JUSTIFIED pessimism, thank you very much. I have absolutely no idea what to do. I’m also AWFUL at making good decisions when my emotions and fantasies are pulling me in an opposite direction from my logic. I was the sort of kid who always peeked at the alternate endings in my Choose Your Own Adventure books before making a choice. Also significant: The choice I was usually leaning towards had the worst ending. So there’s that.
What was I supposed to do? My first promising dating situation in forever, rising like a Phoenix from the ashes of countless rejections and failed attempts…and he’s DIVORCED?!?
Of course, my biggest questions (Did you cheat on her? Did she cheat on you? In 2,000 words or more, please explain in detail exactly why you married her in the first place, and what went wrong. Who filed for divorce, and on what grounds, and is she insane, and do you expect that your child will be well adjusted notwithstanding the broken home? Do you want to have more children? Has co-parenting been going well thus far? What are your thoughts on the appropriate size and scope of a second wedding?) were a little too, um, penetrating for right that minute. Instead, I listened, held back my burning questions, and ate my blueberry buckwheat pancakes with pure maple syrup.
Our conversation eventually eased back into much less problematic terrain, and we even had a few laughs before I gathered up my stuff and headed back to my place. He brought up a great new high-end sports bar in River North and suggested going for a late dinner and drinks on Thursday. I tentatively agreed. A little voice in my head was screaming, “No! No! No!” But it was far less persuasive than the butterflies and visions of cushion-cut diamonds in micro-pave settings that appeared when he kissed me goodbye and walked me out.
As the cab made it’s way down Lake Shore Drive, I stared at the frozen lake and recalled the simpler days of two weeks ago, when my biggest fears about Carson had to do with the pratfalls of dating a fellow attorney from my firm. A few moments later, I got out my BlackBerry and added “watch nat’l championship game with Carson” to my Thursday schedule.