Dining, Dating, and Dashing

As a first-year I was elected into the leadership of the Student Investment Committee. As a sophomore I ran a handsome campaign for SGA President, and escaped the burden of winning by losing handily. As a junior I met the Dalai Lama and won the TEDx spot to talk about traveling. As a senior I’ve published a centerfold piece with the Middlebury Magazine and installed an art exhibit at the Burlington Airport.

I’ve been to 47 states and will finish all 50 by graduation. Ron Liebowitz helped me secure a summer internship. I ride horses; I ride a black bicycle; I’m pretty good at spelling. I’m a dynamo. Yeah, some people might even call me ‘kickass.’

But none of this really matters because, romantically, I’m a total washout. I’m blessed with great friends, talented and praiseworthy each in their own right, but I’ve been single since 14. And even my last relationship was just a teenage “romance” with a middle school girlfriend I managed to fall irreparably in love with, despite never having even held her hand.

After that preposterous heartbreak, I was indifferent to any romance less than true love. “Once you’ve had steak, it’s hard to go back to McDonald’s,” I reasoned to my friends. Boarding school gradually eroded this absurd idealism. Drunk first-year nights in social house basements also played their part.

I modified my romantic philosophy: “Enjoy steak when you’ve got it, but eat McDonald’s while you wait.” I’ll admit I’ve had my share of both clowns and golden arches — and maybe the occasional Big Mac.  My feelings toward the matter might be described as a mild regret.

But a 5’6” Asian boy who wears earplugs to parties (because he has tinnitus, a legacy of the middle school rock band) has a little more hill to climb with the girls at an Atwater madhouse than do the shapely, athletic white men. I do fine when I can converse in a lit room with shoulder space. The reality is that being short and looking foreign doesn’t cut too fine a suit at a campus dance party.

More than that, meaningless hook ups are almost as dissatisfying as holding out for Sleeping Beauty. But there’s a middle ground: casual dating. I’ve slowly become a believer in this nebulous territory. As a single man, there’s too much to gain to not take little risks.

So, I ask girls on dates … and make tons of mistakes. I’ve tried leaping out of the friend zone a couple times: goodbye, friendships. After one date, a girl invited me to a party where she made out with someone else when I stepped away to the punch bowl. Another girl was alarmingly sick, oddly refused to let me buy her coffee, then waited until I followed up a few days later to tell me she was already seeing someone.  I’ve had some terrific dates too. I went to a museum in Manhattan on one; after we split, I headed to Brooklyn and got my first tattoo — totally unrelated though memorable nonetheless.

This biweekly column is a solution to three of my goals: dating, eating free food and writing publicly.  Every two weeks, I’m going to take a different date to a different restaurant downtown that I’ll persuade, in advance, to give us a free meal. I get a date, the girl gets a story, we both get fed, the restaurant gets publicity and hopefully we all get a good laugh.

This all just might work out, and I hope by now you’re rooting for me. Encourage all your female friends to say yes if I come a-askin’.  After all, it’s just a date! And who knows, maybe my first date will be smashing and I’ll have to abruptly end this column for true romance.