My White Castle Romance

I wrote an essay about my "White Castle Valentine" and read some of it for my appearance at Gelf Magazine's Non-Motivational Speaker series. Here is that excerpt ...

It started very innocently. I read a post about a White Castle Valentine’s Day promotion on Gawker, a NYC media and gossip blog I was contributing to, and left a comment indicating how the news caused me to experience a small orgasm in my mouth. I subsequently blogged about it on my own site and figured that would be the end of it. But not long after posting I got an email saying, "If you have a contest to win a White Castle date with T.A.N., I’m so there.”

Hmmm. My mind raced with possibilities, but I knew I’d need reinforcements. So I passed the email on to one of the Gawker editors and told them if they were interested, I was game. They jumped on it; and next thing I knew a couple photos, setup posts and days later I was choosing the “Win A Date with TAN” contest winner. Her name was Rachel: white, graphic designer, and according to her, in possession of a booty that made guys stop on the basketball court. And yes, she had me at "booty that makes guys stop on the basketball court."

Now who knew you’d be able to use the words “media buzz” about an ironic White Castle Valentine, but over the next couple days the promotion and contest were mentioned in the NY Times amongst other papers and websites. On Valentine’s Day I was getting text messages and phone calls from people I hadn’t heard from in years, all wishing me good luck with the “White Castle chick.” It was surreal.

But at that point in my online life, Surreal and I were good friends. We met in the fall of 2005, soon after I started blogging, and quickly became close. Fact was my whole dating life had transformed into some type of new media reality show — one with no producers, cameras, or television slot mind you — but all based on the premise of me exclusively dating people I met through my blog for about a year and a half. I imagine Mark Burnett would call it “Beauty and The Blogger,” or “Romancing The Blog,” or “For Negro or Love.” Some such thing.

Now this wasn’t a conscious decision mind you, I never solicited for dates, or posted about my personal romantic life. I was coming out of a long-term live-in relationship and had zero experience with online dating. So who knows how it began; maybe it was my oft-mentioned prep school pedigree; or the avid peppering of prose with parenthetical “hollas”; maybe it was because I showed more than a little love for alliteration; or maybe this was just status quo for a new blogger on the scene. Whatever the reason, somehow or another, my site had become a chick-magnet. An incredibly weak chick-magnet, that barely stays on the refrigerator without help from other magnets, but a magnet nonetheless.

My series premiere was a rousing success. A couple months after starting TAN I was invited to the 30th birthday party for a local sex columnist, and at the bar I could hardly mask my snickering as I got my first taste of people complimenting “The Assimilated Negro.” “Haha!” I thought. “They just used the word ‘negro’ with a straight face. Victory is mine!”

A few hours later, episode one would close with me making out on the street with the girl who invited me. The critics — who also freelanced as my friends — raved. The season looked promising.

But the bloom fell off the rose in the next episode when an otherwise average evening on the town would devolve into an unexpected one-night stand with a psycho-blogger. During a display of coital schizophrenia that would make Norman Bates grab his meds, and other guys grab a meat cleaver, she manic-depressively pulled me in and placed my hands on her body, before turning her head and telling me to “please, go away.”

When I then backed off she’d plead, “No, wait! Come back. I want you.” I almost wished I had viewers to text message in and tell me to “Go for it!” or “Get the hell out of there!” I didn’t know what I was doing.

But only a couple weeks after checking out of the Psycho-Chick motel, I found myself downtown in a writer’s apartment discreetly fingering the fishnet stockings of the femme-blogger sitting next to me. We had just met in person for the first time earlier that evening, but our numerous prior IM flirt sessions provided a more-than-adequate comfort level. There we were sitting on the floor in a circle of six people — four girls, two guys — when my hand decided to go confidently in the direction of its dreams. And I can only imagine her shock when five minutes later, I was lying down on the kitchen floor with two other girls on top of me; one kissing me, the other doing something that would probably be pulled down from youtube.

Now there had been some drunken talk about orgies earlier, and I distinctly remember using the word “girth” in an inappropriate way (is there any other?). But I thought those were jokes. And I thought these were all-talk-no-action bloggers. Who knew they were so ready to make it happen in the real world? Where was this going to lead? I remember the image of me waking up in a ditch somewhere with my laptop and the word “Fidelio” spray-painted all over it briefly flashing across my mind.

But for better or worse, the orgy never actually came to pass; the mood shattered when Fishnet-Girl would announce she was leaving. As everyone sobered up and sheepishly acknowledged they didn’t really want to participate in an orgy with relative strangers, Fishnet-Girl pulled me aside and asked, “what are you doing?” The question felt so familiar.

"What are we doing?

Rachel was asking me what we were going to do after White Castle.

The dinner had gone about as well as $10 Valentine dinners for two go, and Rachel was as advertised. Face: cute and smiley; Personality: charming and bubbly; Dress: short and clingy. My kind of girl. But I couldn’t quite tell if we were really connecting, or just getting along out of obligation.

After getting random emails and text messages throughout the day, it felt like me, Rachel and everyone we know were rooting for this zany rom-com sequel to Harold and Kumar go to White Castle. We couldn’t disappoint and do something like not like each other. Every laugh we shared premised a question: Were we just acting for our invisible audience? Was this a one-off publicity stunt, or did this Blind Date 2.0 have legs?

Well when in doubt, I always consult my own personal Oracle: alcohol!

“I thought we’d go to this wine bar I know a little further downtown.”

I lived nearby in East Harlem (or SpaHa, as I like to say the kids like to say), so further downtown meant the Upper East Side, where ambience and atmosphere go to die. A little risky, but I knew I’d receive points for knowing the one oasis of downtown style yet to be smothered by the stench of generic beer and interminable “Now That’s What I Call Music!” soundtracks.

Sure enough as Rachel and I loosened up over a bottle of Pinot, the specter of the contest began to loosen its grip on us. During a typical work day you take in a healthy dose of cynical “Valentine’s-Day-is-for-suckers” talk; but that chilly night we basked amongst couples who were as earnest as sunshine in july. And as our glasses filled with red, our hearts filled with romance; and slowly but surely Rachel and I transformed from "The White Castle Couple," to just another boy and girl looking for a connection— with sliders on our breath.

And our connection, like the tension, was building by the glass. When we stepped outside in the freezing cold to share a bummed cigarette (neither of us "smoked"), we had that wonderful moment when bodies hover over each other, still respecting that last vestige of personal space, yet bracing like a sea captain for the imminent breach. Kisses never lie. And ours was the kind that booked a second date without saying a word.

But before the second date, came the Inferno….. and The Inferno was the challenge that lurked in every episode when weird internet life and dating life intermingle....

(to be continued ...)