Bossypants (7 page)

I realized my predicament early in my First Year. We don’t say “freshman” or “senior,” etc., at UVA because Mr. Jefferson felt that education is a lifelong process. Thomas Jefferson—another gorgeous white boy who would not have been interested in me. This was my problem in a nutshell. To get some play in Charlottesville, you had to be either a Martha Jefferson or a Sally Hemings.

During my First Year, I had a crush on a brainy, raven-haired boy from my dorm. This played out like the typical sexy coed letter to
Penthouse
. He would ask me at least once a day if I had ever seen the movie
Full Metal Jacket.
I would remind him that I had not. He would then describe parts of it to me.

After several weeks of mistaking this for flirtation, I tried to kiss him one night by the Monroe Hill dorms and he literally ran away. Not figuratively. Literally.

I did go to one fraternity formal with a devastatingly handsome guy named Awbrey Madison Cartwright III from Georgia. I mean, this guy looked like Clark Kent, no joke. He held my chair for me and opened doors. He was genteel and attentive. There was only one problem. Here’s how our exchange went when he invited me to the formal:

Tina sits on the steps in front of the theater building, chatting with friends from acting class.

Awbrey Cartwright approaches.

TINA: Hey, Awbrey, you’re gay, right?

AWBREY: (thrown) What? No. I was coming over here to ask if you want to go to my formal with me.

TINA: Oh. Sure.

I was right, by the way. He was for dudes.

So you can see why, when I occasionally had a little success with a heterosexual white male, I dug in and hung on for dear life. And this is why I climbed Old Rag Mountain at night.

There was a kid, older than me, an architecture student who did plays in the drama department on the side. I won’t use his real name because I think he’d find out about it and it would give him too much satisfaction. I’ll refer to him instead by how he looked at the time, which was like a handsome Robert Wuhl. Go spend an hour trying to picture exactly what that could be and pick up the book again when you’ve got it.

Welcome back.

Handsome Robert Wuhl and I were in a few plays and some acting classes together. He seemed to appreciate my sense of humor. Like all boys at that time, he tried to talk like David Letterman, which I appreciated. I don’t remember how we first came to be making out in a car, but it was awesome so I kept doing it. Should it have been a “red flag” to me that these incidents would only take place under cover of night, in the back driveway behind my on-campus housing? Absolutely. Was it “not great” that there was never any actual “date” before these events and that it was a secret? Of course. But I finally had my hands on a thin-lipped white boy so everybody just shut up about it!

Secret make-out time went on for a while. Handsome Robert Wuhl claimed to have some ethical/religious reasons for not going all the way, which was fine by me, as I would have been terrified. I say “claimed” because I think it was closer to the truth that he was just a control freak who thought he should save himself for someone hot.

Sometimes there would be a big drama department event, like a party to celebrate the opening of
The Robber Bridegroom
or a wine and cheese reception to welcome guest artist Aaron Sorkin (totally true). Handsome Robert Wuhl would take a pretty date to the party while I attended with friends, and then he’d pick me up later for car sports. Sometimes we would just drive around. We hit a deer once.

Why were we just driving around the Blue Ridge Mountains? To this day I do not understand what this boy was up to. Was it a control experiment to see how much boring nothingness I would put up with before we finally made out? Possibly.

We did eventually go on kind of a date. He took me to the mall to help him shop for a present for another girl, and he bought me a sandwich at Hickory Farms. “You can really eat a lot,” he laughed when I finished it. I was certain that he would eventually be so impressed with my ability to eat like one of the guys that he would want me to be his girlfriend.

So when HRW asked me casually if I’d like to climb Old Rag Mountain with him, I said yes immediately, then raced home to tell my roommates. Clearly I was very special to him. Why else would he invite me to climb a nearby mountain? They were skeptical.

I met HRW the next evening at his off-campus apartment. Yes, the climb was going to be at night. I didn’t question this because I didn’t know anything about rock climbing and I assumed that we were in this for the romance. He introduced me to one of his roommates, Jess or Chris or something. He was a wiry little guy who would be joining us on the climb. This was news to both me and Jess-Chriss. To say he was unfriendly would be the biggest understatement since the captain of the Hindenberg said “I smell gas.”* He alternated between ignoring me and shooting me disdainful looks that clearly said “Who is this ugly off-brand non-sorority girl ruining our homo-erotic bro-times?”

We drove out of town a little ways, listening to Peter Gabriel’s “In Your Eyes.” HRW played that song constantly. He was very deep. Did I mention yet that he always wore a small shell necklace and he told me that he was never going to take it off until Apartheid ended?

It was dusk when we got to the bottom of Old Rag, and when HRW and Jess-Chriss realized that neither of them had brought flashlights. After a quick debate about whose fault it was, they decided it didn’t matter and we should just start climbing.

The first leg of our journey was the walk from the parking lot to the beginning of the actual trail.

It was about a mile and a half. By the time we got to the foot of the mountain, I was already nauseous from overexertion and trying to hide it. I asked for some water.

“Aw, are you kidding me?” The two bros looked blankly at each other. They had also forgotten to bring any water.

The next, more difficult portion of the trail was the “rock scramble,” a feat requiring serious concentration to find a foothold and safely navigate up, over, and in between slippery rocks. It was getting dark now, but there was bright moonlight. It was difficult, but I was actually enjoying the challenge. Jess-Chriss continued to wish I was dead and/or better looking. HRW climbed ahead of us both, showing off. I learned that night that there are markers on these kinds of trails, one color for the easy path, one color for the intermediate path. I also learned that sometimes, especially at night, these markers are hard to see.

Soon HRW told us he was “going off the trail” and he’d meet us after a while. Neither Jess-Chriss nor I was happy about this, but I guess HRW was just too good a climber to be held back. Jess-Chriss and I climbed along in silence for about twenty minutes. If Jess-Chriss had trouble finding the next marker he certainly didn’t get any help from me, because I was a hiking novice. I was wearing wrestling shoes, for example. Jess-Chriss kept calling ahead to HRW to “stop showing off” and “stop being a dick.” HRW

would call back through the dark that he just wanted to try something and he’d be back on the trail in a few minutes. And then we heard it. A grunt and the sound of little rocks rolling down bigger rocks and then a sound like a bag of laundry bouncing and scraping down your basement steps. That idiot had fallen off the mountain.

Jess-Chriss and I must have had the same thought: “Am I going to have to explain to this kid’s mother how he died?”

TINA: We were climbing Old Rag Mountain in the dark on a weeknight.

MOTHER WUHL: Is this your girlfriend, young man?

JESS-CHRISS: No.

MOTHER WUHL: Were you my son’s girlfriend?

TINA: No, ma’am, but he did once tell me that I could be really pretty if I lost weight.

MOTHER WUHL: What the hell were you kids doing up there?!

TINA: Well, I can’t speak for Jess-Chriss, but I was hoping for a leisurely night-climb followed by some over-the-jeans action.

JESS-CHRISS: Me, too. But then
she
was there.

We called frantically to HRW. After a few minutes, he answered. We followed his voice back down the trail and found him. Jess-Chriss climbed out onto the rocks to help HRW over to the trail. He was banged up, but it was somehow decided that we should continue up the mountain. The last half mile or so was not as steep, and we finally made it to the smooth granite top, where we sat down to take in the beautiful dark panorama of the Shenandoah Valley. HRW motioned for me to sit near him, and Chriss-Jess knew instinctively to go sit far away. Tired, dehydrated, and nauseous, I was still ready to try to make this work if there was any funny business to be had. But HRW didn’t touch me. Instead he stared wistfully out at the night sky and told me about the last time he’d climbed Old Rag. It was two days prior, during daylight. He had brought his friend Gretchen up here for lunch. He really liked her, he confided in me. Liked her so much that he didn’t quite know what to do about it. After they had gotten all the way to the top and had the picnic lunch he’d prepared, he offered her a piece of Trident gum, and Gretchen—he had to stop and smile at the adorableness of this—Gretchen had asked him to tear the piece of Trident in half because it was too big for her. “Can you believe that?” he marveled. A girl so feminine and perfect that half a piece of Trident was the most she could handle.

I tried to process what this meant for my evening.

“So… you and I will not be dry humping, then?”

* * *

The way down from Old Rag is a forest road. We found a stream in the woods and finally got a drink of water. We scooped it up with our hands and it was the greatest, most satisfying drink of water I ever had in my life. “Oh the water, / Get it myself from the mountain stream,” I sang over and over again in my head. I was listening to a lot of Van Morrison at the time, because I was also very deep.

It was sunrise by the time HRW dropped me off. As weird as the night’s events had been, I couldn’t help but be excited about the fact that I had climbed a mountain. I never would have thought I could do that. I think someone should design exercise machines that reward people with sex at the end of their workouts, because people will perform superhuman feats for even the faint hope of that.

As I crawled into my bottom bunk, I thought about how I had climbed Old Rag. I thought about Gretchen, the girl who could only accommodate half a piece of gum. “I hope you marry her,” I imagined saying to HRW, “and I hope she turns out to have a cavernous vagina.”

Young Men’s Christian Association

At 5:10 A.M., the el train from the Morse stop in Chicago to the Davis St. stop in Evanston is surprisingly safe for young white women. The only people on the train at that hour are Polish women on their way home from cleaning office buildings all night. They share plastic containers of pale Slavic food that you know is buttery and delicious. It’s just potatoes, rice, meat, and cabbage in an endless series of combinations.

My first and only day job (so far) was at the YMCA in Evanston, Illinois. I had moved to Chicago on Halloween of 1992, pulling into Rogers Park with people whipping eggs at my dad’s Pontiac in accordance with the holiday.

I had never waited tables, and my attempt to lie about that to the manager of the Skokie, Illinois, Ruby Tuesday was unsuccessful. “Where did you work?” “The Carriage House in Havertown, Pennsylvania.” My more worldly friend from home had told me to make up a restaurant and give them her phone number. “Did you do hand service or tray service?” “Tray.” My friend from home had told me to say “tray service” because it’s easier. “What was your favorite thing about waiting tables?” My friend from home had not anticipated this question. “Um… the children. Waiting on cute kids… It was a family… restaurant.” Game over. While “the children” may be a good nonsense answer for a Miss Universe contestant or a gubernatorial candidate, anyone who has ever waited tables—or simply gone to a restaurant with a child—knows that children are the soul-sucking worst. They take all the sugar packets out of the bowl, spill milk all over the place, and their wasted meals only cost five dollars, as compared to a nice booze-drinking adult to whom you might be able to up-sell a crispy onion-and-jalapeño crappetizer. I did not get the waiting job.

I applied for a job as the night box office manager of a small theater company in Boystown. The job paid about five dollars an hour for a four-hour shift, so I was surprised to find that it required a lengthy interview with the artistic director of the theater. I had a degree in drama, I explained. We talked (meaning she talked) about playwrights we (she) liked. It was between me and another girl for the job, and she needed to know what I had to offer the Tiny Pretentious Theater Company because

“We like to think of ourselves as the most exciting theater company in Chicago.” I tried a joke. “I like to think of myself as the most beautiful woman in the world. But where will that get either of us, really?”

The other girl got the job.

My mother arranged for a friend to see me at a downtown lawyer’s office for a receptionist job.

I wore the electric blue polyester Hillary Clinton power suit that my roommate and I shared for such occasions. The hourlong train ride and scramble to find the exact address had made me late, and by the time I got to the interview I was sweating my roommate’s BO out of the suit. The stench of every drink and every cigarette she’d had the last time she wore it filled the high-end office in which I interviewed.

Between the suit, its booze cloud, and my thick virgin eyebrows, I was deemed unfit to answer phones in plain view. I was turning out to be college educated and unemployable in even the most basic way.

Thankfully, my electric-blue-suitmate was an uninhibited vagina about town. She hooked up with an early Obama prototype named Marcus who worked at the Evanston YMCA. They were looking for someone to work the front desk from 5:30 A.M. to 2:30 P.M. I got the job! Evanston is the diverse suburb just north of Chicago where Northwestern University is. The YMCA there was a great mix of a high-end yuppie fitness facility, a wonderful community resource for families, and an old-school residence for disenfranchised men. It may also have been the epicenter of all human grimness.