Avoiding Prison & Other Noble Vacation Goals

by Wendy Dale

  WENDY: Will I have the same job in three months?

  MAGIC 8 BALL: No.

  WENDY: Will I be broke in three months?

  MAGIC 8 BALL: No.

  WENDY: What is to become of my life?

  MAGIC 8 BALL: Your future is inexplicably intertwined with that of Wink Martindale.7

  Since I never did get my hands on that Magic 8 Ball (meaning that the preceding conversation never actually took place) when I met Wink Martindale three months later, needless to say, it came as a complete surprise to me.

  My life changed with a phone call. When I received it, I had been at my wit’s end, wondering how I was going to pay my rent and the stack of bills that kept piling up while I survived on Top Ramen and adrenaline. The division of Hughes Aircraft where I had worked for the past two years had quit on me (before I got the pleasure of quitting on it), recently having transferred its operations to Arizona, so I had been struggling with the new reality of living without a regular paycheck.

  If I had ever been in need of good news, it was certainly that night sitting outside on my porch, nursing a Manhattan, staring at what was left in my glass and realizing that it was my last cocktail; there wasn’t money left to spend on any more sweet vermouth. I heard the dim ring of the phone and fiddled with the latch on my door, racing to get inside in time. It was a friend from college, which was nice enough news in itself, but better yet she was calling to tell me that she’d just gotten hired at the Advocate, a gay and lesbian newsmagazine, and that the editors were looking for someone to write profiles on celebrities. It would only be sporadic work, but I figured that any income was better than what I was subsisting on now and it turned out to be relatively easy. My job consisted of basically going around and asking famous actors how they felt about gay people. (In case you’re wondering, Billy Crystal said he liked them, Jane Hamilton said she liked them, and John Lithgow said he liked them but not nearly as much as he liked dressing up in a skirt and pearls.)

  It was a good beginning, but it was still a tenuous existence. For the next few months, I just had enough to pay my bills, assuming I never ate out and was careful at the grocery store. I needed to augment my income with another freelance client, but I had no idea how to go about it. I tried everything I could think of—I walked around my apartment practicing saying I was a journalist, I bought myself a supply of spiral-bound notebooks and Uniball Deluxe pens—but these preliminary attempts were futile. What else could I do? I figured it wouldn’t hurt to sit outside my friend Lisa’s building with a laptop attempting to look writerly. Fortunately, this managed to do the trick.

  One day as I literarily sat on her front steps, her neighbor Bill walked by. I had spoken to him many times before, but I had never managed to grasp how he afforded the rent on his sixteen-hundred-dollar apartment while earning his living as a writer. He had occasionally thrown out clues, referring to his past in New York advertising and his subsequent move to Los Angeles to work in the film industry. Once, I had gone up to his place to take a peek at his ad copywriting portfolio and had noticed that his living room was full of scripts, but how did a writer go about getting such jobs?

  Bill’s life bore no resemblance to my own. He drove a brand-new Saab convertible and got free tickets to exclusive Hollywood screenings. And he had just gotten a job writing a brand new sitcom, or so he informed me as I sat on the steps with my clunky out-of-date laptop. Speaking of which, would I have any interest in interviewing for the ad copywriting position he was leaving behind? It paid five hundred dollars a day.

  He was so casual about it. It was the job he was discarding—to him, it was just leftover material. But five hundred dollars? A day? That would put me in the same league as engineers, doctors, lawyers, and prostitutes. All I had to do was go in for an interview and convince the ad agency owner, Chuck Blore, that I was the writer he was looking for.

  Bill acted as if it was no big deal, but I knew that Chuck was a powerful man. He had worked with Hollywood celebrities. He was friends with TV network presidents. He had personally produced all the radio spots for AT&T’s “Reach out and touch someone” campaign. What could he possibly see in an ex-corporate writer like myself?

  A few days later as I nervously trudged my way up the stairs to his Hollywood office, my chances were actually a lot better than I suspected. Chuck had a personality trait that was about to work in my favor: he prided himself on making brave choices. He had hired Drew Barrymore before anyone had even heard the phrase “E. T. phone home.” He had been taping Christina Applegate’s voice since she was a baby. Chuck loved being able to spot new talent. He took chances on people, paved the way for their success, and watched as they moved on to bigger and better things.

  The first time I walked into his office, he seemed genuinely happy to see me, treating me like the guest of honor at a dinner party. He had me take a seat, and before there was time to introduce myself or exchange a few words of chitchat, he enthusiastically popped a cassette into his stereo. “These are some of the radio spots I’ve written,” he announced grandly, pressing play on the machine.

  He listened to the tape as if hearing it for the first time. He laughed at the jokes, acted surprised by the endings. His pride was that of a little kid, a joyous five-year-old who shouts out to his mother, “Look what I can do!” I found him completely endearing.

  I wondered what I could say to convince him that I was the writer he needed, but once the tape had finished, Chuck seemed uninterested in discussing my experience, a lucky break for me considering there wasn’t much of it to discuss. He instantly hired me on a trial basis based simply on a gut instinct he had about these things.

  Fortunately, I was a quick learner. After turning in a few mediocre scripts, three days later I came in with a radio spot that had him laughing out loud and he immediately upgraded my trial-basis status to that of a full-fledged writer.

  As if the entire experience hadn’t been ludicrously lucky enough, the good fortune that followed was the stuff of freelance writing legend. Chuck had been trying to get a television project off the ground for thirty years—one week after he hired me on, the deal finally came through. I arrived in his office just moments after he received the news. Giddy with excitement, he raced over to me and gave me a warm embrace. “Ever-Lovely,” he said, using the nickname that he would call me from that day forward, “now that you’re my writer, I have a new challenge for you. Have you ever thought about writing for television? I want you to help me script a TV program.”

  A week later the executive producer of the program walked into Chuck’s office for the first time. It was none other than Wink Martindale in the flesh.

  While other people slaved away at their jobs, trapped by convention and an oppressive sense of impotence, at age twenty-five, I had found the secret trapdoor out. I felt like Jim Carrey finally fleeing The Truman Show. I was like the bubble boy inhaling his first breath of mountain air. It was incredible. I had stepped into the life I had always imagined.

  The glee was a little bit hard to take. It was such a novel sensation for me that I wasn’t quite sure how to behave. I didn’t know the norms for happiness. What did happy people do? How did they behave? For God’s sake, where did they shop?

  If I was having a tough time getting used to my newly prosperous existence, my ATM was even slower to be convinced. Several months into my freelance writing career, I had tried to deposit a check totaling more than eight thousand dollars, but even the normally agreeable Wells Fargo machine seemed to have a hard time buying it.

  I had begun the normal transaction process by keying in the total amount of my check. “You have entered eight thousand dollars. Is this correct?” I hit the OK button, figuring the next step would be to insert my deposit envelope—but it was as if this ATM machine had known me personally: “You have entered eight thousand dollars! Are you sure this is the correct amount of your deposit?” This screen had never come up in the past. I didn’t even know this screen existed. I had never been wort
hy of the incredulity screen before. With a big grin, I hit the OK button one last time, realizing that I had finally joined that small rank of people who enter eight thousand dollars on the automatic teller key pad: the wealthy and the dyslexic.

  For a while, the idea of having money was more fun than spending it. In my mind, I squandered my entire wealth dozens of time, reveling in pretending to empty my bank account more than actually going through with it. I could buy six hundred bottles of Absolut vodka, I imagined, picturing a whole side of my living room suddenly transformed into a wall of crystal. Or I could purchase a dozen Macintoshes, two for every room of the house. Or I could go to my favorite Goodwill, and like a millionaire let loose on a capricious shopping spree I could clean out the store’s entire inventory.

  Of course this was all just a good-natured game. I was never really in danger of relinquishing my entire net worth to the Absolut bottling company. I had already spent the past year planning what I would do if I ever got my hands on a significant chunk of dough: I was going to buy irresponsibility.

  Unlike happiness, which seemed to be a result of wisdom, acquired experience, or a lifetime spent in the self-help section of Barnes and Noble, irresponsibility could only be purchased. It was the ultimate luxury item. Poor people never got to be irresponsible without suffering for it. If they didn’t get their student-loan application in on time, no college for them. If they decided to have one more margarita and ended up an hour late for work the next morning, no job for them. But all of a sudden, these rules didn’t apply to me.

  My new freelance existence had the capacity to transform my life. I was just twenty-five years old yet I was already going to avoid all those years of drudgery and office work endured for decades by my father. I wanted life to be spontaneous. I needed freedom the way other people craved money or fame, and my recently acquired wealth suddenly made this possible. “I think I’ll go to Cuba next week,” I said with the same ease that other Americans used when they made plans to visit the supermarket.

  This didn’t gel particularly well with many of the people I knew. Even my travel agent seemed to need some sort of justification for my whimsical decision to flee the country. Was it a vacation? Was I going with some sort of political group? No, I explained, no reason. I simply figured Cuba would be the ideal place to pick up the things that were missing from my life: I lacked rum, I lacked cigars, and having been out of college for several years now, I missed having communist friends. (See, this really was just like a trip to the grocery store—I even had a shopping list.)

  Had I given the trip more forethought, I might have gotten nervous about the prospect of going. Twenty-five-year-old women didn’t just hop on international flights to Cuba by themselves. I would be traveling alone in a part of the world where it was unthinkable for women to do such things, but I was determined to be brave. It wasn’t like I was going to a completely unknown place. Latin American culture was familiar to me. Cuba would be like Honduras—with the addition of communists and salsa music.

  The fact that it was illegal to go there was slightly more worrisome. Even though I had experience in this particular area (Lebanon didn’t exactly top the State Department’s list of recommended vacation destinations), in Beirut I’d had a friend picking me up at the airport. And had something bad happened to me there, say for instance, losing my passport, Peter would have found some plausible way out—such as sneaking me across the border to Jordan where we would have entered the U.S. embassy in Amman and smiled up innocently at the officials, explaining that we were two American kids backpacking through the Middle East in need of a replacement passport—and by the way, did they know the way to the nearest international youth hostel? (For your information, the answer to that question is “Go north forty-three hundred miles and when you hit Europe, hang a left.” )

  But Cuba didn’t have friendly bordering countries such as Jordan. Cuba’s nearest neighbor was well, us, and we weren’t considered exactly friendly.

  The State Department’s official policy has been that the embargo we have against Cuba is economic. Therefore, it wasn’t illegal to visit the island—it was just illegal to spend money there. This didn’t make a great deal of sense to me, but the man who continually supported this paradoxical legislation was the same man who had gotten himself mixed up in a lawsuit, in which he went to great lengths to explain that although a White House intern had provided him with a few oral favors, this, however, did not constitute a sexual relationship—which sort of put the whole Cuba logic into clear perspective.

  However, it was common knowledge that Cubans welcomed American tourists to the country. All I had to do was jet down to Mexico and pick one of several flights headed to Havana each day.

  There are a few tricks for getting into Cuba that any American visiting the country illegally should know. The first challenge is successfully passing the luggage inspection. Now every country has those questions on their customs forms that everyone giggles about, no one takes seriously, and to which you dutifully check off “no” on the cards they hand out on airplanes. Those are the questions about whether you’re bringing in livestock, carrying arms, smuggling narcotics, and so forth. Of course there are the trickier decisions such as deciding whether to declare your liquor when you have exceeded the allowance by say, a dozen or so bottles, but in general the questions are pretty straightforward (except on my recent trip when I’d been handed the card printed in Arabic).

  Unfortunately, customs officials in Cuba take their jobs a little more seriously than those of other nations where a sense of humor is still legal. I had placed a neat little row of X’s down the “no” line of the customs form (after all, I had come to Cuba to buy contraband merchandise; I wasn’t bringing any in), so I was a little surprised when the guard standing watch over the X-ray machine spotted something suspicious looking on the monitor as my bags made their way through the conveyor belt.

  “You may enter Cuba,” he said pulling the offending item out of my luggage, “but not with this.”

  It was an apple. A nice big red juicy apple. The officers would let a capitalist-bred American illegally into a communist country but not if she wanted to bring in things like produce. So that was my choice: some of the world’s best rum, cigars, and salsa music or onefifth of the recommended daily allowance of fiber.

  “No problem,” I said to the guard, adding my apple to the trash can overflowing with illicit peaches, grapes, and bananas.

  “No agricultural products,” he explained apologetically.

  “I thought you were talking about things like sheep.”

  Then it was onto immigration, which was a simple enough process. While all the Dutch, German, and French tourists added a Cuba stamp to the back pages of their passports, I had the guard kindly place the stamp on my visa, a little white card stapled to my passport that had been issued to me by my Guadalajaran travel agent.

  And that was it. I uttered an enthusiastic “Gracias” and officially entered Cuba.

  Umberto was a thirty-something businessman from Mexico City, and when I learned that this was his twelfth visit to Havana, I figured it wouldn’t be a bad idea to tag along with him. Of course, it actually was a bad idea, a real doosey of a bad idea, but hindsight always comes into focus after the fact.

  Meeting him had been a strange coincidence. We had casually struck up a conversation at the Guadalajara airport where we discovered that we were both departing on the same flight to Mexico City. Then we found out we were sharing the same plane to Cuba and that we even had reservations at the same hotel in Havana.

  It turned out that we had a lot in common: I was going to Cuba because I had nothing better to do; he was going to Cuba because he was divorcing his wife and had no one better to do. But he wasn’t into gringas, he informed me on the taxi ride to our hotel. Or smart women, he added, rolling his eyes at what I assumed was my intellect.

  Luckily, I had ruled him out as a potential romantic partner already. It had happened sometime after we
had met and sometime before he began yelling “Death to all Americans!” out the window of the cab. One minute we were driving along discussing Cuban food and beaches and the next minute, he was shouting with his fist in the air, “Yanquis go home!”

  Needless to say, his outburst had come as a bit of a surprise. Luckily, he noticed my startled expression and quickly explained himself. “Don’t worry, I don’t think that way at all. I was just reading that sign over there.” I looked over and caught a glimpse of the writing on the wall: a spray-painted anti-American slogan.

  “I’m Mexican,” he continued. “And we like Americans. It’s just the Cubans who are against you. It was just a sign. There, you feel better now?”

  “Umberto, what country did we just leave?”

  “Mexico.”

  “And what country are we in now?”

  “Cuba.”

  “Do you really think I feel better now?”

  At that moment, I suspected that hanging out with Umberto was going to be one irritating incident after another. Sure enough, by that evening, this premonition had been confirmed: It was annoying talking to him, it was annoying being with him, and it was annoying having to hang out with so many hookers.

  Umberto had insisted on an authentic Italian meal. And my first night in Havana, there definitely was a pizza on the table, but with all the prostitutes in front of me competing for a place on Umberto’s lap, it was hard to concentrate on picking off my anchovies.

  Umberto grinned over at me, happy as a boy in a Nintendo factory.

  “Which one do you think?” he whispered over at me as a peroxide blonde in a tight orange dress ruffled his hair.

  “So many to choose from—difficult, isn’t it?”

  “Yes. I’m so glad you understand. A Latin woman would never understand. Take my wife, for instance. She would never be sitting where you’re sitting now.”

  “I imagine she wouldn’t.”

  “Are you having a good time? I want you to be having a good time, you know.”