If at Birth You Don't Succeed (15 page)

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Baltimore, despite being called the “Charm City,” has the distinction of being Edgar Allan Poe's hometown, the setting of the HBO show
The Wire
, and home to a rat problem only surpassed by its heroin problem. When Betty rolled across the city limits that summer, we were greeted by a fanfare of police sirens. Our hotel in the center of town was conveniently located across from a condemned Burger King. We were too drained from our traffic-plagued drive to Maryland to even care that our rooms' ACs were on the fritz. Sweating and exhausted, we hit our pillows and promptly fell asleep, all of us grateful that tomorrow would be a day off.

The next morning, I was startled by a sound that is only alarming when you hear it through a bathroom door while sitting on the toilet. A young woman's voice drifted through the walls, and I listened to Josh laugh and converse in a voice pitched half an octave higher than his normal register. I didn't need to make out a single word to know that whoever he was talking to was as hot as a summer's day and as refreshing as a dish of sherbet. Josh's type was so specific that his flirt voice acted like sonar, so I knew the person on the other side of the door must have dark hair and very large breasts. When I emerged from my morning constitutional, I demanded to know who this mysterious beauty had been. It was the front-desk clerk who'd come to switch us into rooms that weren't a thousand degrees. All I knew of this woman was what I could gather through a closed door while pooping, but I was nevertheless enchanted and emphatically called dibs.

“Do you have a plan as to how you're gonna woo this girl?” Josh asked.

I had only thought it through as far as asking my friends to stop pursuing her so I wouldn't have any competition. Despite my good intentions, I had no idea how to transition from crushing on a girl to actually going on a date with her. Realizing I was entirely out of my depth, Josh spit-balled some ideas. “Why don't you set up a romantic dinner on the rooftop and Brad and Aaron and I could come out dressed as fancy waiters?” All ridiculous scenarios aside, I knew I'd never have the courage to ask this girl out for coffee, much less dinner. My best-case scenario, if I actually did work up the nerve, was to be let down easy. So I shifted my objective to something less ambitious: proposing marriage.

If my romantic gesture was so grand that it could be perceived as a joke, then being turned down would be a joke too. Her rejection wouldn't be that quiet “no” that tenses your chest and closes your throat. By choreographing a hyperbolized romantic stunt for the cameras, I could avoid admitting that I had no idea what I was doing with women and was too terrified to even attempt a first move. I was warming up for a “bit,” rather than dreading a cold shoulder. There were chains around my heart even thicker than the ones that kept the squatters out of the Burger King across the street.

It was on this day off, while weighing the comedic value of getting the front-desk lady flowers against the cost of a bouquet, that I got a call from a twenty-three-year-old reporter, who we'll just call Stephanie. She worked for a college paper I'd never seen or heard of, but to us, any press was good press.

I was used to doing these interviews by now. None of the questions ever surprised me, and they usually ranged from “What made you want to make a travel show with the Internet?” to “Whatever happened with that Oprah show?” Stephanie, however, did surprise me. When she called, she seemed giddy to talk to me and spoke with an excitement I thought was reserved for fans of much more attractive people. Five minutes into the interview, she asked, “What time would be good to do the interview?”

Confused, I said, “Well, I'm free all day…”

“Okay, great!” she said. “I'm in DC now, so if I take the train, I can be there a little after six. Would that work?”

“Sure,” I said, moderately bummed out that I'd have to put on pants that day. “But I don't want you to have to drive across the country!” I continued, because, with my complete lack of geographical knowledge, I had no idea that Baltimore and Washington, DC, were relatively close. “We could just do it by phone,” I offered.

“No, no, it's fine. It'll be a lot better for details anyway if we're in person,” she assured me. “I'll just hop on the train now,” and she hung up before I had a chance to explain that this would really disrupt the evening I'd already planned to watch
What About Bob
with Josh, Brad, and Aaron over Thai food.

What an inconvenience it is that a woman wants to talk to me!
I thought, which is a perspective that might explain my dearth of romantic encounters as much as anything else. It was my responsibility to pick the meeting place, but the only things we'd seen in Baltimore were the super touristy national aquarium area and The Block, which was home to both the Grace and Hope Mission and about a dozen strip clubs. Instead of splitting a footlong with Stephanie at the Subway next to the Hustler Club, I opted for the slightly classier Cheesecake Factory located next to the aquarium and the plastic dragon boat rental place.

I got there around seven o'clock and was greeted by a girl with long brown hair, slightly frizzed from the humidity, in a floaty tank top and white shorts. We got situated at a table outside and ordered dessert. I hadn't eaten dinner and was really hungry, but as a rule, I don't generally eat big meals when I'm out with people for the first time. There's no better way to play into a stereotype of helplessness than to have to ask someone, “Can you cut up this chicken?” immediately after introducing yourself. But Stephanie and I didn't have any of those awkward interactions and there was a certain ease of conversation that was almost completely foreign to me.

I didn't have to use any of the canned responses to standard interview questions that I'd perfected over the past two years of being in the spotlight. I thought I'd only be there for half an hour before I could hop back in bed and fall asleep to Bill Murray, my toes gently grazing Josh's leg hair. But before I knew it, the short interview had progressed into a three-hour-long stream of consciousness. I was asking as many questions as I was being asked. I learned that Stephanie was a nanny, that she was moving to Australia, and that she had been engaged but had recently broken off her engagement. Normally, the only information I got from reporters was formal, like, “Hi, I'm Dan from
Time
magazine. Let's get started,” or “My name is Natasha. I'm from a podcast called
Lick It, Bite It, or Both
. You've been nominated as someone we'd like to lick and bite. Would you be interested in being interviewed?”
1
But this was not that same staunchly professional dynamic I'd grown accustomed to.

Normally when you're doing press, there's some element of performance. But with Stephanie, I felt comfortable dropping all the formality because of something I'd later come to recognize as chemistry. But since I had limited exposure to girls enjoying my company, I was unable to imagine this evening progressing into anything beyond our pleasant conversation. Besides, I had other things on my mind—it was nearing ten o'clock and the
Riding Shotgun
crew had a very important morning ahead of them. We had to be up at seven to go to the Hidden Peak Cat Club “Strawberry Fields” Cat Show. I would not only have to interview very enthusiastic and serious cat owners in the morning, but also train cats to run through an obstacle course, if not run through one myself. I was first and foremost a host on a job. My mind hadn't been conditioned to think of the action I could be getting, and it hadn't occurred to me that there could be something more beneficial than eight hours of sleep. But Stephanie seemed to at least vaguely know of something that I might rather be doing.

“I just bought all this stuff for an eighties prom party I've got next week,” she said, pointing to a shopping bag. “What time is it?”

“Quarter to ten.”

“Damn,” she said.

“What's the matter?” I asked, signing the check and backing away from the table.

“I don't think I'm going to be able to catch a train back to DC tonight, and my phone's dead.”

“Huh,” I said. “What kind of phone is it? I've got a charger back at the hotel you could use,” a casual offer that for me held the subtext of
I've got a cell phone charger back at my hotel room that you can use to charge your phone.

“That'd be SO helpful!” she said, and we started walking back to the Best Western Plus together.

When we got to the hotel, I was relieved to see that my future wife's shift was over. I didn't want her to think I was cheating on her when I brought another girl back with me. Stephanie stopped at the front desk and said, “You know what, it's really late. I should probably just stay here.” Had I not been an idiot, I would have taken this glaring, flashing neon sign as a cue that I should offer up my room as a place to stay, but, obviously dedicated to remaining a virgin forever, I said, “Oh, I'll get you a room!”

“No, I got it,” she said, taking out her wallet.

Newly minted key card in hand, she asked, “What room are you staying in? I'll show you the dress I got for the party! You can tell me if it's too tight. It's a leopard print thing.”

Naturally, at the prospect of a pretty girl trying on tight animal print dresses in my hotel room, my train of thought was
How long is this fashion show gonna take? There is no way I'm gonna be ready for the cat show if this girl is trying on outfits all night!

So, before Stephanie even checked out the private room I'd chivalrously let her book, we went up to my floor. Josh had already been asleep for an hour and had he not been groggy, I'm sure, like any good friend, he would have assessed the situation, taken me into the bathroom, and finally clued me in to what an oak tree could have gathered was a surefire chance to lose my virginity. Well, maybe it was a stretch to think that a woman who'd only split a slice of cheesecake with me would usher me all the way into manhood that night, but regardless of what base I got to, this was certainly the best opportunity I'd ever had to get in the game.

But it was Stephanie who ended up in the bathroom and when she emerged she was in a form-fitting leopard print tube dress with her hair done up in an eighties scrunchie. In retrospect, I painfully recognize that this look was totally hot. I enthusiastically told her she looked great, but I have to admit that in the moment the dress mostly just made me wonder if there would be any leopard print cats at the Hidden Peak Cat Club “Strawberry Fields” Cat Show in the morning.

Gosh
, I thought,
if I get any less than six hours of sleep, I'm gonna be completely shot for tomorrow!
So in lieu of acting like a real human being and proposing that we go to her room so she could try on the rest of the outfits she'd brought, I yawned and said, “Well, I've got a really big day tomorrow so I should be getting to bed! Do you want me to come by your room in the morning so we can check out the breakfast buffet?” Reinvigorated for all the wrong reasons, I said, “They've got one of those automatic waffle makers; it should be awesome!”

“Yeeaah, so just, I'll see you in the morning, then?” she shrugged, realizing it was hopeless.

“Definitely!” I said, reassuring her that, and I quote, “I never miss a chance for waffles!”

And with that, Stephanie went down the long hallway to her room. As I went to bed, I thought to myself,
Well, that was nice!

I awoke the next morning to waffles, still oblivious to the fact that I'd missed out on anything more the previous night than a full forty winks. So as Stephanie left the breakfast bar to catch a train to DC, I recounted the evening's events to Aaron, who instantaneously was able to translate my night with Stephanie at the Best Western into what it actually was—the best-missed opportunity in the Western Hemisphere.

“You let her get her OWN ROOM?!” he shouted in disbelief. Then, turning on Josh, “How could you let this happen?! This was
our chance
!!!”

Not yet ready to confront my own shame, I joined in: “Yeah! How could you let this happen?!”

It made me feel slightly better to pretend that this all might somehow be Josh's fault. I was only twenty-seven! I didn't know any better! Josh was a full two months older than me. He'd clearly been the responsible adult in this situation.

“I'm sorry,” he lamented, burying his head in a bagel. “I should have done something!” he exclaimed, with all the sincerity of a firefighter who couldn't save your kitten.

“I'd expect this from Brad, but not from you,” Aaron continued. Brad just shrugged his shoulders in agreement and ate his scrambled eggs.

With the burden of guilt now squarely resting upon Josh's shoulders, we resolved that if a situation like this were to ever arise again, Team Get Zach Laid would not fail.