Berkshire School was the first time I went to the jungle. I was exposed to a world of privilege and ease, and I found it baffling in the beginning. I remember one day I went to a friend’s house and she said, “It’s time to do the New York Times crossword puzzle.”
What? A crossword puzzle? Weren’t we supposed to be cooking or cleaning or doing something tangibly productive? The first time I heard the word “brunch,” I was confused. What the hell was brunch?
The deeper I got into the jungle, the more I wanted to live there forever. I was in awe of how many Ralph Lauren sweaters these kids had and grateful we wore a uniform to school so I could pretend that maybe, at home, I had those sweaters, too. I got a boyfriend from a nearby private school and new friends. One of them lived in Italy during the summers. Another friend had Chanel lipstick. Chanel! Can you imagine? Until then, I’d only ever seen my mother’s Revlon tubes up close. A Chanel lipstick at the time, just so you know, cost about $25! And a Revlon cost $4.99. I remember this because I used to save my waitressing tips to buy them for myself.
I want to talk a little more about friendships because over the course of my life they’ve played a very important role. When I was very young, my brothers and sister were my main playmates, but I was also very social with the kids at school. I was always rounding up friends to play games and chitter-chatter. I liked having people around and I liked interacting. My childhood friendships were a lot like my adult friendships. I had a lot of acquaintances, but I wasn’t very popular. I had a few main friends and a bunch of other people I knew loosely.
It wasn’t until I went to Berkshire School that I started to develop deep friendships. My best friend there was Livia, and like me, Livia was a high achiever. We were more focused on exploring what lay ahead of us in life than we were in boys. We had goals.
Livia’s parents were Italian, but unlike my ethnic family, hers was wealthy. Livia was the coolest friend I’d ever had until that point. In more ways than one, we were total opposites. I was blond with blue eyes. Livia had dark features and was incredibly elegant. My parents were middle class. Livia’s parents had an apartment in New York, and during the summers they traveled to Italy. I thought that was exotic and adventurous. It was so far beyond the bubble I knew.
The first time I went to New York City was not with Livia. It was on a church bus trip with my parents. I’ll tell you about my first impressions of that in a second. What I want to tell you about now is how, near the end of high school, I started going on weekend trips to New York with Livia and her parents, to stay in their apartment in the city. It amazed me. We went to restaurants and shopping and on walks in Central Park. Livia wasn’t a visitor in the city. She treated it like home. Livia was the first person who showed me that New York wasn’t an unreachable place. It could be the place you actually lived.
Livia was fearless and intensely academic, as was I, and as time went on, our friendship became a little competitive. At the end of high school, we lost touch, not because we didn’t like each other anymore, but because when I left home I needed to redefine myself and this meant letting go of my old environment and a lot of the people who were in it.
Livia and my other new friends at Berkshire School really opened my eyes to a new way of living. They had what seemed like endless amounts of free time. Their lives seemed so effortless and beautiful and abundant, and I was just in awe. To be like them became a goal that I was constantly striving for. Doing well in French wasn’t about doing well in French; it was about the possibility of traveling to Europe after I graduated. I involved myself in as many activities as possible. I joined the student council. I became an athlete. I got perfect grades. It became all about being the best.
My mom was incredibly supportive. This dream of achieving something more was one that we both shared. But when I chose lacrosse instead of tennis, I could tell she was disappointed. “Tennis is a sport you can play for the rest of your life,” she said. “And it’s what established people play.”
Along with the certainty that I was going to leave Great Barrington and become successful, there was a lot of doubt. I always feared that I wouldn’t make it. I always feared that people would figure out I didn’t belong. I was fearful all the time. At some point, my goals switched the cart with the horse and the cart got ahead of me. I was no longer the driving force that was pulling my life forward; I was being dragged backwards by my unrealistic expectations of myself. “I need to do my best” became “I am not enough and never will be enough.” There will always be someone prettier, or smarter, or skinnier, so the dream of being the best went from a dream to a nightmare, a journey to nowhere that was exhausting and unhealthy.
As a consequence of all the pressure I put on myself, I developed an eating disorder. I exercised excessively and counted every calorie. The weight loss made me feel like I was in control. It gave me a sense of certainty. If I didn’t eat, then I lost weight. If I kept pushing myself, then I would get to where I wanted to be.
It got pretty bad. All I would eat were watery vegetables and I would go on five-mile runs every day. I developed a layer of fur all over my body—a common side effect of anorexia. My mother was frantic and felt totally powerless. It was the first time she couldn’t fix my problem. Being thin wasn’t just about looking like a model in a magazine. On some level, it made me feel special. I enjoyed my mother obsessing about my weight because it meant that all of her attention and concern was on me. For better or for worse, there was a part of me that wanted to be taken care of by my mother in the doting way I had been when I was little. When you’re about to be swallowed up by a vast sea, you’re not afraid to swim farther away from the shore if it means you can grab hold of a buoy.
One night during dinner when I was doing everything but eating my food—cutting it up, moving it around my plate, pulling the bread off my burger, trying to imperceptibly tuck the meat into my napkin when no one was looking so I could throw it out later—my mother lost it. She stood up, and with a force that was more urgent than it was angry she shouted, “You better snap out of it, Dorinda, or you’re gonna squander everything you’ve worked for! You’ll either end up in the hospital or I will put you there if I have to.”
My mom had reached the end of her rope. The reality of how my eating disorder could hurt my future and separate me from my family was worse than the twenty pounds that separated my old body from my new one. I slowly got myself healthy again, but the longing for that feeling of control that I had when I was anorexic lingered beyond the weight gain. Eating disorders are demons that are attracted to a specific flavor of vulnerability and insecurity—and those insecurities never really go away.
After letting go of my eating disorder, I put my energy into my future. I kept moving forward, and I kept my big dreams. It would take me a long time to realize that this—the determination to constantly move forward—was something I could use to my benefit. Hard work and determination in the pursuit of my goals became a huge part of my value system as I got older.
When you’re operating from a mentality of scarcity, it’s tough to see the bigger picture, particularly when you lack a sense of what the world looks like outside your neighborhood. For many, many years, I couldn’t see the bigger picture at all. I could only see the next step in front of me. At seventeen years old, though, I came face-to-face with the big picture I was meant to see: New York.
The first time I went to the Big Apple was with my parents, as I mentioned. It was on a church trip to see the Rockettes at Christmas. It was a very big deal. We booked the trip in June, and I spent the next six months looking forward to going to this mystical place I’d only ever seen on television.
In December, I boarded the Peter Pan Bus with my parents, and when we drove over the bridge I was just dazzled. Sometimes you have high expectations of a place and then the reality of it is a letdown. Well, New York wasn’t that at all. If anything, it was better than I’d imagined. The minute I saw all those bustling people and felt all that energy, I
knew that this was where I belonged.
Technically, I barely stepped foot in Manhattan that day. The bus drove us straight to the Rockettes performance and straight back to Massachusetts afterwards. And my mother insisted on holding my hand for the short time we were out on the sidewalk, because she was convinced that I would be kidnapped. To her, the city was like Alcatraz, full of thieves and rapists. “This is where the alligators live,” she said.
“Mom, I’m going to live here one day,” I told her.
“No, you’re not, Dorinda. You can move to Boston, but not here.”
My mother was right about almost everything, but I knew that when it came to me and my destiny in New York she was wrong.
Madonna once did an appearance on American Bandstand, which was a show I watched religiously. When Dick Clark asked her what she planned to do next, she said, “Rule the world.”
I didn’t know how I was going to get back to New York City or what I was going to do when I arrived, but I knew that one day it would happen and that when it did it would feel like I had conquered the world.
Fool me once, shame on me.
Fool me twice… don’t fool me twice.
Chapter Three THE BIGGER PICTURE
As we all know, life doesn’t always give us what we want, but we have to take what we’re given and make it work to our advantage.
At the end of high school, I applied to college. I’d excelled at Berkshire School. I’d joined all the groups and gotten good grades. I’d done my very best. For my classmates, money wasn’t a factor in choosing a college, but for me, it was. It was understood that I would attend the college that awarded me the most scholarship money.
I applied to Franklin & Marshall because my brother Johnny had gone there on scholarship, and I applied to Boston College, which was where I really wanted to go. Everyone at Berkshire School wanted to go to Boston College in those days. It was prestigious and it was especially appealing to me because it was only two hours away from home, whereas Franklin & Marshall was a whopping five hours away in Pennsylvania.
Boston College rejected me. I was so discouraged. But did I choose to sit back and quietly accept this rejection? No, I did not. I made an enormous fortune cookie with a fortune inside that said: “DC belongs at BC.” My mother drove me down to Boston College and I left this fortune cookie with the president. Shortly after that, I was put on a wait list. I thought I had a good chance.
Maybe I would have eventually made it in as a student at Boston College, but I would never find out, because while I was waiting, Franklin & Marshall accepted me and offered me a scholarship. My father had a stern conversation with me. “You’re going to Franklin and Marshall and that’s it.”
I was incredibly upset. I’d tried so hard. I’d overachieved. And meanwhile, classmates of mine who’d achieved far less slipped into Boston College and other schools because their wealthy parents had contacts there or had gone to those schools themselves. For the first time, I truly felt like life wasn’t fair. I’d been raised to believe that if you did all the right things you were going to be okay, but at this moment I realized that wasn’t always true. The world did not always reward your good efforts. But it did always reward wealth and connections.
I was sullen as my parents drove me to Pennsylvania, and I was heartbroken when my mother said, “See you at Thanksgiving.” Thanksgiving was months away! How was I not going to see my parents until Thanksgiving? As I watched my parents drive away, I was completely overwhelmed, thinking, What have I done?
For the first semester, I was depressed. I missed home all the time. I’d never spent the night anywhere other than my parents’ house and my grandparents’ house, and now I had to share a dorm room with a nutty girl I didn’t know. From the very first night, she was bringing guys back to our room. It was just foreign to me. I was still a virgin then and used to the cozy, safe environment of my childhood home. Once a week, I would call my parents from the dorm pay phone, but we couldn’t talk for long because it was expensive. On every call, I cried and told them about how much I hated college.
Although I was terribly homesick at first, I slowly came to understand that I had to engage. Other than Christmas break, spring break, and summer, I couldn’t afford to go back and forth from Lancaster to Great Barrington, so I had to find a new support system at school. I made friends with many new interesting people, a lot of whom were different from me. Some of them were in sororities. Others were more artsy. At college, I learned to be open to new people and situations, and I really blossomed.
I was always on the go, and even though I had to work while I was in college and keep up my grades because I had a scholarship, I always found time to socialize. Franklin & Marshall is a smaller school. It had about twelve hundred students when I was there. Fraternities and sororities were big and each house attracted a unique group. I was good at going between groups, although I was probably most drawn to Chi Phi because its members were preppy, a lot like the kids at Berkshire School. They had formals and cocktail parties they liked to call smokers. And they played preppy sports like lacrosse, tennis, and squash.
I arrived at Franklin & Marshall with a lot of the preppiness I’d picked up from Livia and Berkshire School, but at heart, I was kind of a hippie. I loved Crosby, Stills & Nash. I had hair down to my belly button. I wore wild outfits, like an IZOD shirt with a denim skirt and a bunch of multicolored scarves.
One day in the quad, a fellow student came up to me with a huge smile on her face and said, “Hi, my name is June. I like your skirt.” June became my first deep and long-lasting friend. I was drawn to her because she had the same childlike sense of wonder and silliness that I had. We were both sort of immature, and when I was with her I felt like I was home. June had attended a prep school like I had and she was a hippie, but an elegant one. She resembled a young Candice Bergen. Smart and kind, June was a mix of a fairy princess and flower child. She was ethereal and wacky, but in a grounded, relatable way.
June and I loved to sit in the quad and talk for hours. One of our favorite things to do was exercise—and boy, did we exercise. We walked excessively; we worked out to Jane Fonda tapes; we swam endless laps (while pausing to chat) in the Olympic-sized pool at the school gym. After, we’d go to the salad bar at Wendy’s, where we’d raid the carrots section. The more I got to know her, the more I realized how much we had in common. Neither of us had ever had a serious boyfriend, we liked the same music, we had eclectic tastes that set us apart from the norm, and we were both artsy. We loved painting, knitting, beading, and art.
June is still a big presence in my life. Together, we’ve lived through many jobs and boyfriends and adventures. We were at each other’s weddings; we welcomed each other’s babies. After my divorce and Richard’s death, June was there to comfort me.
Looking back, it was a blessing I didn’t go to Boston College, because if I had, I never would have met June. I would have gone home every weekend. So, this is a good example of how what I thought was initially a failure turned out to be the best thing that could have happened.
My friends, and especially June, started to feel like my family, and I began to really enjoy the communal aspect of college. Back then, nobody was hiding in their dorm room scrolling through Instagram. We were in the quad or the student center hanging out or in class or at the library studying.
The work-hard-play-hard mentality at Franklin & Marshall was right up my alley—and it was kind of an epiphany. I had always worked hard, but now I could have fun, too. I got good grades and took my classes very seriously, because, as I was the first girl in our family to go to college, there was no way I was going to let myself or my parents down. And in addition to all that hard work, I also learned to have some fun.
One night at the dorms, I met a member of the Chi Phi fraternity named Billy. Billy was preppy and cool and he played the saxophone, and I quickly fell madly in love with him. I was so innocent back then that I thought when you fell in love you would get married and have
children and build a life together. That’s what my parents had done, so those were my plans for myself, too.
I’ve heard a lot of people talk about their first love, the one they never got over. Well, that love for me is Billy. I think I still love him, even today, maybe because he was the first. From the moment I saw Billy, I loved him.
Before Billy, I’d never been boy crazy. And I didn’t consider my sexuality much at all because it just didn’t exist in my house growing up. The idea of losing my virginity was a big deal. For the rest of freshman year, Billy and I dated, but I refused to sleep with him. He made fun of me for that, but I also think it made him want me more.
By the time I went home after freshman year, I loved college so much that I couldn’t wait to go back and see Billy and my friends. That summer and every other summer during college, I focused all my energy on working and making money. I waitressed at the Red Lion Inn, and let me tell you, I was not a passive waitress. I would take every single shift that opened up. I’d offer a deal to the waitresses who I knew were single mothers: “You can go home to your babysitter. I’ll pick up your table. And we can split the tip. What do you think?”
When that first summer was over, I went back to Franklin & Marshall with all the money I’d saved and reunited with Billy, who was not only the sexiest man I’d ever seen but also my best friend. I was just crazy for him, but sadly, so were all the other women at college.
During my sophomore year, I finally slept with Billy. It was the beginning of the end. After that, things changed. We didn’t break up, but we never became an item either. No one could figure out if we were together or not, including us. It was tumultuous and passionate and ultimately not very healthy. We’d break up and then we would get back together. It would go astoundingly well for a while, and then he’d disappear from my life.
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