Confessions of a Dating Fool Read online

CHAPTER 2

  The Doll in Vermont

  Her name was Adrienne.

  She was my boss. It was my first job out of business school. I was an Assistant Account Executive at a big Madison Avenue advertising agency, living in New York, New York. From my first day at work, which was a hot, steamy summer day in the City, I wanted to impress the hell out her and everyone else with my work ethic. I assumed everybody else wanted to be the president of the agency some day too. But I’d be that guy. That was the plan anyway.

  I have perfect recall of my first day at work. I showed up in the personnel office at quarter to eight on a Monday morning, fifteen minutes before the official start time. I was pitted out, stupidly, from walking thirty city blocks from my apartment on the Upper East Side on a day that was soaring to record heat. Thank God I wore the navy blue suit. Its polyester fabric didn’t cling, and it helped hide all the perspiration stains. Had I worn my other suit, the tan cotton one, I would have looked like I’d been hosed down by one of the doormen on the East Side washing off the sidewalk in front of his building. My agency was on Forty-fourth Street, across the street from Brooks Brothers, the source of my future wardrobe, one without polyester.

  I got to work fifteen minutes early, only to learn that I was actually an entire day early. When I walked through the door marked Personnel, I introduced myself to the receptionist, an older, stern looking woman who had entirely too many worry lines on her face. She recognized my name but confused me by asking me what I was doing in her office before my first day. She enlightened me by saying I wasn’t expected to report in until tomorrow. I didn’t really feel like a fool, like some people might have—nope, not me. I just looked at her and told her I couldn’t wait. I was ready—so what if I was a day earlier than expected? She smiled and had me wait a bit, but eventually, I was given a handful of forms and shown a cubicle on the fourth floor.

  The cubicle was rimmed with file cabinets under piles and piles of loose-leaf folders. It had become the floor’s junk room, and it sat in the middle of a handful of other empty cubicles that could have been clones. But it was my cubicle, and it had a desk and a chair, and it was the starting point of what I was sure would be a stellar career. I spent my first “unofficial” day filling out personnel forms and reading handbooks on agency policies. It was a snap. Later in the day, I was given an organization chart for the agency team assigned to the General Mills account, which was the agency’s biggest client, and I was told I’d be on that team, although my name wasn’t on the org chart yet. I couldn’t wait. I was anxious to learn who my boss would be, see my name on that chart, and get my career officially underway.

  I was sure I could be the best Assistant Account Executive the agency had ever seen, and I was willing to do whatever it took. That’s what I said to myself and, of course, being a Midwesterner meant that honesty and ethics were deeply ingrained in that commitment, so I didn’t literally mean that I’d do anything. It wasn’t until the mid-morning of my second day that the nice lady I met the day before in personnel took me to Adrienne’s office, introduced us to each other, and spun on her heel to leave me with the encouraging words, “I hope I don’t see you again, at least not for a while.” She said that with a smile, on her way out the door. I didn’t have a clue what she meant. No matter—I was face to face with Adrienne and ready to work.

  Before the day ended, I had learned that Adrienne was quietly known around the office as “The Doll,” a spin off of her last name, which was Dollinger. Cute as hell—she was a doll, so it made perfect sense to me. She was indeed very attractive and fit my image of a senior executive in a Madison Avenue agency. She looked polished and very stylish, yet business-like, but not in a hard way like businessmen can look. She had a subtle air of quiet strength and confidence about her, yet she retained the soft edges of femininity. Like me, she was from the Midwest, which might have had something to do with why we hit it off right away. She was from Illinois, somewhere on the far northwest side of Chicago. I was from Wisconsin. I grew up outside of Milwaukee on Lake Michigan, just north of the city, only a hundred miles north of Chicago. We weren’t exactly neighbors growing up, but she reminded me a little of the older sister of one of my buddies back home. I was sure I was going to like working for her, and not just because she was so easy on the eyes. After an hour with her, it was easy to see that she was very together, clearly competent, and very focused, with nothing airy about her. I was looking forward to learning a lot from her. A lot.

  The first six months as an ad guy were almost behind me. Those steamy hot August days were distant memories, all overrun by a quick but colorful autumn in Central Park and the early onset of cold winter winds whipping up and down the city’s cavernous avenues. Winter was wild in New York that year, almost fierce, making the walks to and from work brutal when the wind was up. Lots of snow fell, and a couple of nasty northeastern blizzards hit in early January, which sent commuters home prematurely. It didn’t take much of a snowfall to shut the city down and make getting around difficult. In the first few hours of any heavy snowfall, city life was threatened into an uncommon silence, as blankets of white crystals smothered the mayhem and turned the city into an unbelievably beautiful winter wonderland. Sadly, the beauty of it all never lasted very long.

  I was a hard worker, learned a lot, and kept at it with a diligence that was single-minded toward making my client contacts very happy. I must have been doing some things right because shortly after the beginning of the New Year, I was surprised with a “secret” bonus that required a pledge of silence. In fact, I was told that I’d be fired if I told anyone. No one was to know—not a soul. It became clear that salary and bonuses were top secret and not to be discussed by anyone, ever. Adrienne knew about it, of course; she had engineered it all, and being my boss, she was the one who gave it to me. I thanked her and swore I’d keep it a secret. It wouldn’t be the only time that silence would be the best policy.

  In late January, the agency’s Toyota account team was buried under its own blizzard of work that was required for a big mid-February plans presentation to the client. All the TV campaigns would be reviewed along with the copy and media strategies. The stakes were high—millions of billing dollars could flow in or out of the agency’s coffers as a consequence of these presentations. It was a three week push before the big meeting, and every team member was under the gun and committed to putting in the time. No one was leaving the office before eight o’clock at night, and like a lot of the other junior executives, I was working till midnight, night after night, and showing up in the mornings as early as six. I had earned a real office the month before, one with a door and four walls that went from the floor all the way up to the ceiling. It had one window overlooking a dingy air shaft, but it was a fantastic improvement over the cubicle I’d started in. It was quiet and it was private. The latter quality was especially nice. It meant I could get a lot done in peace and expect a modicum of privacy whenever someone dropped in.

  On the last Thursday of January, Adrienne walked into my office late in the afternoon. She was wearing one of Diane von Furstenburg’s wrap-around dresses in a bright red geometric print, one of many geometries that made up the latest rage for executive women who were looking for alternatives to dressing in business suits like men wore. She looked great.

  “How’s it going?” was her entry line as she propped her slender frame against the slender frame of my open door. Her frame had a lot more curves.

  “I’m doing great,” I replied and asked, “Wanna meet over something?”

  “No,” she said, hesitating for a moment, as if in search of a word. “Do you ski?” It was the first question she had asked of me in two weeks that didn’t have anything to do with work.

  “Yeah,” I replied, “but it’s been a while. Never in the East. You?”

  She enlightened me. “Yeah, a lot lately, in Stowe. I have a ski rental up there for the month, and this weekend is my last weekend.” I knew that Stowe was in Vermont. It was a pret
ty famous place for skiing. She continued, “I booked it last summer.”

  Right away I felt bad for her, thinking she would have to give up her last weekend, with the big work push underway. I guessed too that it probably cost a bundle. I waited for her pain and watched her look shift from me to the ceiling and then back to me. I could tell something was up.

  She laid it on me: “If you’re not doing anything this weekend, we could drive up there tomorrow afternoon, turn it into a weekend of work, but get a little skiing in.” She paused, looking for a reaction from me.

  This weekend scenario ran through my mind quickly—very quickly. I didn’t have any plans, but that didn’t make it a good idea. I stalled, wanting more information. She read my thoughts.

  “We could leave the City at five tomorrow—I’ll drive—and be in my cabin by midnight. It’s a big place, a couple of bedrooms, close to the slopes. We can work Saturday morning, ski in the afternoon, work some more at night, work some more Sunday morning, take another run, and drive back at the end of the day. Easy.”

  It flowed from her like it had been rehearsed. She had thought this through but must have been wondering if I’d take a pass because I still hadn’t said anything.

  “So, to ski or not to ski? That’s the question, Tom.” The name at the end of the question was a nice touch.

  Clearly, to me, she was my boss, and the only answer to her question was a resounding yes because I wanted her to know I was a terrific worker. How could I say no, especially knowing she needed all the numbers I was working on? Skiing was appealing too, no doubt about that. And I could tell she didn’t relish the idea of not using her cabin. Without missing a beat, right on the heels of her mauling of Shakespeare, I said “Yeah, let’s do it!” She smiled, happy with my acquiescence, and walked away, tossing a “Good!” over her shoulder.

  When I walked into my office just before six that Friday morning, I was the first one on the floor. I stashed my bag in the corner of my office behind the door, out of sight. I didn’t need people in the office asking about my weekend plans. I’m sure Adrienne was counting on my discretion. Neither of us wanted anyone to get the wrong idea—or any idea at all, for that matter. At a little after five o’clock, we fled the office, separately, a minute apart, met outside a hundred feet uptown from the lobby entrance, and cabbed it to her parking garage near her place on the Lower East Side. She drove a BMW 650, a pretty hot car. It didn’t surprise me. It fit her. After a couple of hours of difficult but typical Friday traffic going north on I-95 toward Vermont, we broke free of it all, just as we left Connecticut behind us. At that point, it became evident that she didn’t particularly believe in speed limits. We’d be pulling into Stowe well before midnight if it didn’t snow en route.

  It started snowing an hour out of Stowe, and it got heavier by the minute. Midnight was already behind us because of the snow, but that was fine; it promised exhilarating runs the next day through plenty of fresh powder. We made it to the foot of the driveway leading to the cabin, stopped by a three-foot snow drift, just short of the cabin’s front door by about a hundred yards. Snowshoes would’ve been nice, but all we had was perseverance with high stepping through the freshly fallen snow. This was done by me twice, once for each of our suitcases, which were shouldered alongside my head with one hand, while the other gripped one of the briefcases. Thankfully, her skis were already in the cabin. I would have to rent what I needed tomorrow. Adrienne’s arms were piled with two shopping bags of provisions acquired on the drive up. The second trip I made up the driveway was easier, as you might guess, because I traced my footsteps from the first trip.

  When I was done playing mule, Adrienne had the lights on, along with some music, and was fiddling with the contents of the shopping bags. The cabin was all cozied up, missing only a roaring fire in the fireplace. When I walked in with the second suitcase, I dropped a couple more shoefuls of snow on the threshold. The woodpile was just outside the front door under the eaves and stacked high with dry logs, waiting to be tossed into the fireplace. Instinctively, I knew that was my next mission.

  Fifteen minutes later, with our coats off, we stood side by side in front of the fireplace, taking in the heat from the first flames of the fire I built. We watched as my fire lit up big, with the help of plenty of newspaper and three dry logs that were crushing lots of kindling. My competence was immediately reinforced. I went to the door and plucked my briefcase from the threshold, set it on the cabin’s only big table, popped the brass clasps, opened it, and spread my papers in a neat row, like race horses in the gate. I was ready to work. I glanced at Adrienne by the kitchen counter and at the bottle of red wine in her hand. It was already open and filling a wine glass. The drive had been long, the hour was late, but we were excited about being there. I was guessing that she was just as excited about the weekend ahead of us as I was. I felt giddy about the mission ahead and a chance to show her my dedication, not to mention showing off a little on the slopes, so I was thankful when she poured the red into a second glass, happy to celebrate our arrival with her.

  “To a productive weekend and lots of fun!” she said, as she raised her glass.

  We clinked and I added, “Sounds good to me. Cheers!” The wine was very good, and I was very thirsty from the drive up. It hit the spot.

  Then, for an instant, while we shared the moment in sipping our wine, standing face to face, barely two feet apart and looking directly into each other’s eyes, I felt I was on a date. It was an easy thought to have—a very easy thought to have. It was an irresistible thought, an unstoppable thought—for me, anyway. I didn’t have a clue what she was thinking, but I knew what I was thinking. Here we were, just the two of us in a woodsy cabin in a winter wonderland a million miles from anywhere. A fire is roaring in the fireplace and warming up the place, the edge of a week of work is behind us, the light of two floor lamps is soft, barely competing with the soft shadows from the fire’s flames, as they danced on every wall and surface.

  All this, and Adrienne is looking really good. Really good—every bit of a doll. And why not—she is, after all, “The Doll.” For a split second, I’m thinking only one thing, and the thought surprises me like a hot ember falling into my hand. Yeah, we might have something here, something more than logs might be igniting. And then the fantasy bubble popped with the realization that Adrienne is my boss. What was I thinking! “She’s your boss,” my inner voice repeated over and over: “Your boss, your boss, your boss! You work for her! Your career is in her hands,” it warned, “You better watch what you’re doing!”

  I look down into my wine glass, lean into it, swirl its deep dark lusciousness round and round the inside of the glass, inhale its full, robust, cherry chocolate bouquet, get a grip on my thoughts, and take another hearty sip and look up again, meeting her eyes, knowing that it’s going to be a very difficult weekend if I have to behave. And, surely, I have to behave. She’s my boss, undeniably.

  With the renewed eye contact, I repeated her words, “To a productive weekend!” intentionally neglecting to reinforce the “fun” offered in her toast. I don’t think she noticed. After all, she surely was aware that I was there because I worked for her and we had a lot of work to do. Maybe, maybe we could get some skiing in, but we both surely knew what we had to accomplish before the weekend ended.

  The wine was good; it was easy to drink. Adrienne pointed the way to the second bedroom, where I’d be staying, as she carried her bag into her bedroom. She said she was changing into some jeans. I did the same.

  I returned to the living room a few minutes later, having used most of the time to unpack and the final thirty seconds realizing I wasn’t really tired. When I returned to the big room, Adrienne was wearing some old jeans and a white blouse, with a pink sweater slung loosely over her shoulders. She was seated on the couch, her legs curled under her, facing the fireplace with a fresh glass of red in hand. My glass also had a refill and was waiting for me on the coffee table between the couch and the fireplace
. I sat next to her, glass in hand, sipped, and took it all in. It was a great fire, plenty of sputtering and crackle, lots of dancing flames licking the logs before spiraling upward, It put forth just the right amount of heat to make a room all toasty and, yes, romantic.

  We both stared into the fireplace, transfixed by the moment, with wine glasses held up high enough to catch reflections of flames in their crystal bowls of lustrously lit liquid. We chatted a bit, about work, about the drive, about stuff I mostly don’t recall. The wine was good. It was a beautiful moment. It was okay with me that Adrienne was my boss. It was all really very innocent. We weren’t doing anything other than sitting really close to each other, drinking wine, and whispering. (I don’t recall when exactly our conversation dropped to whispers.) With glazed eyes, we were watching the flames curl around the burning birch logs in a fireplace in a pine log cabin on a silent wintry night in the middle of the woods of Vermont, a million miles from everything and under a billion stars.

  Our heads turned, our eyes met, and then we leaned into each other and kissed with lips that barely touched. That first kiss, a kiss of ecstasy, carried the hint of a hidden hunger, an undeniable hunger. I pulled her closer to me. The room got a lot warmer, and I’m thinking the fireplace suddenly isn’t the only source of heat. For the first time, I inhaled her scent and ran my fingers through her chestnut hair, clutching gently, not wanting her to pull back. She didn’t. Her lips were soft and moist, like the little voice inside me told me they would be. The other little voice inside me told me I was kissing my boss and that I should pull back immediately before it was too late. I pulled back slowly, eased up on the throttle, and so did she, maybe with similar trepidation. I didn’t say anything, but I breathed deeply—a breath that she had taken away. We were both silent and went back to staring into the curling flames.

  A minute passed, another sip of wine for each of us, and then we set our wine glasses onto the coffee table at the same time, as if we both knew that we needed more of each other. It was a hunger that couldn’t go unanswered. I wrapped my arms around her as she held on to me, both of us lost in the moment, exploring a new mouth, a new scent, new sensations, and each other close up and tight in. We kissed hard and long, wanting, pausing only to come up for air before another deep dive. My lips moved across her cheek to an ear, and then lingered on the side of her neck before sliding down her jaw line to the base of her chin, and then slowly down the front of her neck. She was purring, with her head tilted upward, making her neck look like the most inviting pathway I’d ever seen. My lips slowly moved a little farther down to her open collar and then downward again a little more slowly, but not by much, only slow enough to take time for my fingers to undo the first of her buttons, then the second. I pulled her closer to me, and took every breath and sigh from her as encouragement for more contact, more tenderness, and more of each other.

  Then that little voice popped into my head again saying, “Stop! She’s your boss! Are you crazy!” I kid you not, dear reader. That voice was back, and loud and clear inside my head.

  I slowly pulled away long enough to hear the voice of reason beg for the brakes, and then I leaned back on the couch, seeking but not wanting a little separation from her. Once again, we both paused in the glow of the fire, and in our glow, I’m thinking we were at the threshold of a moment of truth. I just wasn’t sure what the truth was.

  Adrienne moved to stand up, but not without a little untangling, followed by a sweet kiss to my cheek. She got to her feet and said she’d be back in a minute, then disappeared through the door to her bedroom, which was off to my left. I stared into the red hot embers and wondered what I’d do when she returned. It wasn’t an easy call, as I fought the “boss” thing.

  Two very long minutes later, Adrienne reappeared at her bedroom door. She was barefoot and didn’t move and perfectly framed in the doorway, wearing only a lacy light blue bra and matching panties, looking like she was right out of a Victoria’s Secret catalogue.

  I held my breath over the sexiness of her beauty. A moment before, I thought the next step wasn’t an easy call, but now the call was easy. My eyes ran over every inch of her, imprinting, without any recall that she was my boss. That thought must have disappeared into thin air, like smoke shooting up the chimney, when she took a half step back into her bedroom.

  Our eyes locked. “You coming to bed?” she asked seductively. “We have a big day ahead of us.”

  I was at a loss for words and gave no thought to the big day ahead. All I could think of was the big night underway. I answered her question by pulling my shirt and sweater over my head in one swift motion and dropping the ensemble on the floor while walking toward her, as she disappeared back into her bedroom. I walked through her doorway, successfully fumbling with my belt.

  We collided in a frenzy of lust on top of her bed. We were all over each other, breathless and gasping, our desire intense and rampant—and finally unbridled. We wanted each other and everything about each other, and nothing else mattered. We asked nothing of each other, while giving and giving as much as we had in us. Entangled and lost in a frenzy of caressing and kissing and tasting and rolling over and over, we came together and lost track of all that existed outside the room in a moment that was infinite. Covered in each other’s sweat, we were spent, and moments later fell asleep in each other’s arms.

  When I awoke the next morning, sunlight was streaming through the split in the bedroom curtains, and Adrienne wasn’t in the room. I ambled into the bathroom, aware of the smell of bacon coming from the kitchen. I returned to her bedroom, stepped into my jeans, and walked into the kitchen, wanting to devour anything and everything she’d cooked up for us. She fixed a lot of food, not just bacon and eggs, but English muffins, oatmeal, and a bowl of mixed fruit. I ate it all, while little was said between us and with no acknowledgement of the night’s very real passion other than me saying, “Fun night!” That was followed by a smile from her, indicating she totally agreed, before diving into her coffee. The conversation slipped into plans for the day, and then the day just took off.

  Adrienne and I worked all day and got so deep into our work that neither of us even thought skiing could be a possibility. By the end of the day, our documents were everywhere in some sort of organized chaos, laid out to assist us with the assembly of the first draft of our presentation. Food remnants were everywhere as well, as we had grazed through the day and into the evening on deli sandwiches, bananas and some other fruit, and a big bag of oatmeal cookies. We worked late into the evening, without the benefit of wine, and finally called it a night, making it official with exits to our separate bedrooms. We were exhausted, and a good sleep was the antidote for our mutual fatigue.

  Breakfast the next morning was another round of bacon and eggs, muffins, and anything else that was left from Saturday’s work marathon. Skiing was not on the docket this day either. Neither of us missed it; we knew what we had to do. There was simply too much work to be done, so we worked nonstop until mid-afternoon, finally calling a halt to it all and packing our bags for the drive back to the City.

  Adrienne and I never talked about that night, as if it had never happened. And I never told anyone about it. It was one of those things meant to be kept between us. In the next three years at the agency, I had other bosses, but none like “The Doll,” of course. She became my mentor and had a lot to do with my success and rapid climb up the agency ladder. In my fourth year at the agency, I resigned for a plum job at another agency for an even speedier climb up the corporate ladder and an eventual move to Atlanta to be closer to my Coca-Cola clients. We lost touch with each other.

  Six years and two ad agencies later, I was standing in front of the elevators at The Drake Hotel in Chicago. The doors opened, and for the first time in as many years, I bumped into Adrienne. She was flanked by three other very senior executives I knew from my days at her agency. I greeted the others warmly, then quickly turned to Adrienne for a warmer, more personal greeting. They all k
new she had been my boss years ago. She looked fantastic and hadn’t changed a bit, but I was wrong about that—really wrong—as I was to learn momentarily.

  “Adrienne!” I said with almost overbearing enthusiasm, “Hi! It’s so great to see you again. It’s been what? five years? six? Gosh,” I then blurted, “you look terrific!”

  She looked at me blankly, with an expression of total bewilderment, absent of any recognition of me whatsoever. None. I was immediately stunned and glanced at the others for a flash of enlightenment, but they offered me nothing. Instead, they looked at Adrienne, indicating that it was her turn to speak.

  “I’m sorry,” she said, and continued expressionless, “I injured my head in a ski accident three years ago and have no memory of my life before that. It seems that we knew each other in the past, but I have no recall. I’m so sorry.”

  Upon hearing those words, not only did I easily recall the million moments we had worked together and what a friend she had been to me in the agency, I could vividly recall that one unbelievable night in Vermont, the one we had never spoken of. And now it was surely the night we would never speak of. Never.

  I told her that she was the best boss I had ever had and I was so sorry about her accident. A minute later, we all parted. They went their way, and I pushed the elevator button again, ready to get on with my life. I was sorry over her memory loss, while I would always cherish a memory of a terrific boss and, for one unforgettable night, a terrific lover.

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