Drinking, Driving, and Dexter

Tuesday night I have plans to get drinks with Dexter, a hipster/musician I dated in high school who has since become a pretentious vegetarian investment banker, drives a Saab around Manhattan and regularly brags about how his stocks are on the rise. Such is the life of a young New York banker - he has to work till 9 pm, so my roommate, Alexandra, goes with me to a bar in Chelsea to have a few drinks while I wait for Dex.

Over a shared order of chicken fingers and drinks - cranberry vodka for me and Amstel Light for her - we discuss the pros and cons of potentially dating Dexter.

"He's slightly a douchebag, but maybe he could drive us in his Saab to Chili's in New Jersey," Alex says. One of the only things we dislike about New York City is the nonexistence of the restaurants we frequented in college: Chili's and Chick Fil A.

"Dexter can be a hard dog to keep on the porch," I respond. "He's kind of a pain in the ass, so might not be worth dating him solely for a ride to Jersey."

I am basically over the date with Dex before he even arrives, but when he texts "in a cab," it's too late to cancel.

He arrives wearing a light blue tie; his dark hair is slicked back like an extra on the set of Wall Street. I can't really tell if I find him attractive. He's definitely cuter than he was in high school when he spiked his hair and wore band t-shirts to class, and he's nearly 6-foot-3, which never hurts.

He and Alex exchange hellos and how are you doings, and just like that she is released and out the door.

"Have you eaten?" he asks. I say yes and tell him the chicken fingers aren't very good. He flags down a waitress and orders a chicken sandwich and fries. Further confirmation that he's a know-it-all and doesn't care that I just said the chicken here doesn't rival the aforementioned Chick Fila A.

"I thought you were a vegetarian?" I ask.

"I stopped that two years ago because when CEOs ask me to dinner, we usually eat steaks. I can't very well order tofu salad at a dinner meeting with a CEO."

Of course he'd say that. Pretentious, like I said.

"I'm a simple meat-and-potatoes kind of guy anyway, so might as well," he adds. I tell him I beg to differ, since the last time I saw him he was in fact a skinny vegetarian sporting a new Rolex. Simple those attributes do not make.

We make some small talk about work, order a few more drinks, then he flashes and hands over his gold AmEx to the waitress before the bill even arrives. Showy move, I think, picking up the check before even looking at it.

Somewhere between our barstools and the front door, I talk him into taking a cab to where his Saab is parked so we can take it for a spin. It's so New York that we take a cab to his car, but it's always fun to ride around Manhattan without the ticking of a cab meter.

"So, how's law school going for your brother?" He asks me once inside the car.

Did I tell him my brother was in law school? Surely not, but in a city where most investment bankers date hotty totty girls who come from an East Coast blue blood family and summer in The Hamptons, I am surely not going to deny this. Besides, my brother does happen to be studying to take the LSAT. For the third time. But who's counting? At least he doesn't know my brother is still living with our parents.

"Oh, he's starting in January."

Lie number one.

"Cool," Dex says. "Is he living at home now?"

Shit.

"He's living in uptown Dallas, I think."

Lie number two.

Little does Dexter know right now my brother is probably eating over-cooked lasagna with my parents and bitching about not wanting to do the dishes after. I can just hear him now, "I already set the table tonight, what more do you want from me, WOMAN!?!"

Somewhere between the Upper East Side and the Upper West Side, Dexter's hand is on my leg as he maneuvers his sportscar through uptown traffic. My five or so drinks are starting to kick in, and he's looking slightly more attractive than when he first arrived at the bar. Soon we are pulled over on Madison Avenue, full-fledged making out. I've kissed him before, I dated him in high school for crying out loud, so I figure it's ok to make out in his flashy convertible in front of the Coach flagship store.

At one point my shoe makes a fart noise on the slippery leather seat. Or was it really a fart? I am too tipsy to know the difference, but I wouldn't put it past me. It wouldn't be the first time I have farted on a date, and it sure as hell won't be the last. My friend Kathleen likes to say I poop every time I pee. That's hardly true, but I do think my 95-pound frame stays thin thanks to the fact that if I eat a Big Mac and a McFlurry, I'll crap it out within an hour. I may not have affluent blue blood in my veins, but at least my genes include a good metabolism...

"Want to come back to my place?" Dex mutters, interrupting my thoughts about bowels and genetic codes. I kind of wish I was home watching Dateline with Alex on the couch in our underwear. We don't have central air, so that explains the underwear. We also don't have cable, which explains why we'd be watching Dateline.

"Can't, I have some work to do at like 7 am."

Lie number three.

"Stop being boring," he protests.

"I'm not boring, it's 1 am and I have to be up at the crack of dawn."

Lie number four.

He begs and pleads and generally acts annoying, so I pretend I am getting sick from my drinks, and that does the trick. Moments later we are in front of my apartment. Leaning back in the car after I get out, I thank him for the drinks and the drive. The car door knocks me on the back of the head, and then I stumble into the lobby of my building. On the elevator, I think maybe I should have stayed home and watched Dateline on the couch in my underwear.

Before I enter my front door, Dexter texts, "I wish you were going home with me."

Get a clue, Dex.