Confessions Of A Love Whore

During my freshman year at an all-male Catholic high school, I was infatuated with a straight classmate. As in past entries, I refer to him as "James", because he so strongly resembled my teen romance ideal: James Marsden. James was only in two of my classes, and we never hung out off campus because he lived in another city. Yet I spent the next several years of my life in love with him—even though I never saw him again after the ninth grade. 

Just over a year ago, I rediscovered a love letter that I wrote to James back in high school. I never sent it, but I decided to share it with the world, because  it captured being hopelessly in love and hopelessly sixteen in a way that is universally relatable regardless of gender or sexuality. I timed its posting with the anniversary of Madonna’s Confessions On A Dance Floor, because I love that album like no other and wanted to underline that with an extra special blog post. This year, as the first in a series of deeply personal new entries, I thought I would celebrate “Confessions Day” by sharing the sobering follow-up to my unrequited high school love story. For some of you, it may turn out to be as empathetic as last year’s post, if less nostalgic and more humiliating.

I was convinced that James had feelings for me during that first year of high school, based on many brief but seemingly revealing exchanges. Even accounting for my overemotional adolescent perspective, I don’t doubt I was a little bit right: he was straight, but there still appeared to be something between James and I when we were fifteen...despite of our lack of any physical contact. It was fleeting and youthful, so much so that it would not have lingered on in the memories of people like James who live and grow in the real world. But for a cinematically inclined escapist such as myself, the experience was an unbelievably potent high, and I refused to leave it in my past. So I shed any semblance of shame and relentlessly pursued this literal dream romance. That is, until what began so subtly in our freshman year of high school came to an operatic finish in our freshman year of college.

I spent my sophomore and junior years waiting for my secretly admired to phone me out of the blue, revealing he’d been in love and waiting for my call until it became unbearable to harbor his feelings any longer. After two years of that never happening, I spent much of senior year trying to arrange an opportunity to hang out, hopeful that we could reignite a friendship if I could hide my feelings long enough to make him fall in love with me. Every effort to see one another failed, and I should have left it at that. But I could not allow myself to believe that James would not love me one day. I knew that to an outsider (which, at thirty-one, is what I am today) all of this would appear crazy. But to my eighteen year old self, the craziness was precisely what made it feel so romantic. Or, should I say, “so romantic comedy”.

By the first year of the 21st century, everyone but James knew about my feelings for James. Endlessly bemoaning the hole in my heart took its toll on my social life in the first semester of college, and never more than on New Year's Eve 2000. I was lonely and depressed, so I deliberately avoided Midnight by sitting in a movie theater by myself for the late show of The Family Man. It was my second viewing of the Brett Ratner film in which Nicolas Cage was a wealthy businessman who found happiness in an alternate reality where he’d married and had children with his great love, played by Tea Leoni.  At that time, I was living a life of privilege and being afforded opportunities that I would not be able to fully appreciate until many years later. But I was consumed by the perceived void left behind when James went to a new school and I turned him into a benchmark which no other guy could match. I constantly dreamed of giving up all the monetary perks of my life in order to be with him, if only because such a sacrifice, I thought, would prove that my love had always been real.

My freshman year at Emerson College, and James’s first year in the military, both coincided with the peak of AOL Instant Messenger’s popularity. Somehow I got a hold of James’s screen name on there, and before long we were, like in my dreams come true, "talking" all the time. Right after Valentine’s Day 2001, following weeks of daily correspondence, I decided to throw caution to the wind and tell James everything. And when I say everything, I mean EVERYTHING. What I wrote was not that far off from my unsent love letter in its massive length and total shamelessness. But the difference was that what was sweet when I was sixteen was desperate when I was nineteen. I shared the unsent love letter with the world because I thought it was relatable for anyone who remembers being that age and feeling those feelings. But I cannot bring myself to ever re-read the one that I did send.

James did not get to read the letter for several days, during which time we continued chatting online regularly. Then, one afternoon, I decided to escape my anticipation anxiety with film that I felt paralleled my longing: John Cromwell’s 1934 Bette Davis-Leslie Howard adaptation of W. Somerset Maughm’s Of Human Bondage. It was my second viewing, having seen the film two years prior when I began appreciating the films that made Bette Davis a star. But that day, it was not a piece of cinema history. It was a piece of reflective glass, and it was my life that was being reflected. 

As soon as it ended, I went from my living room to my bedroom, where my pre-wireless laptop was connected to the modem. My AIM Away Message was onscreen, awaiting a response from James. That day, the message was a quote from Edgar G. Ulmer’s film noir classic Detour.

“That’s life: whichever way you turn, fate sticks out a foot to trip you.”

There was no word from James when I got to my laptop, but seconds later, before I could look away from the screen, his response appeared before my eyes. I don’t remember all of what he wrote, except that it was the longest piece of text I’d ever seen on AOL Instant Messenger written by anyone but me. Only the Cliffs Notes version remains in my mind: that he appreciated my friendship and respected me tremendously as a person but that he didn’t share these romantic feelings and would not be comfortable continuing to communicate with me at that point in his life. He was never anything but respectful, kind, classy….all the traits that made me fall for him in the first place. He did not respond the way I had dreamed of, but he wished me well on the rest of my life journey. Had I respected his wishes, we might have crossed paths down the line and formed some sort of friendship as mature adults. I should have left things there, because his message, while unbelievably disheartening, gave me the chance to quit while I was (sort of) ahead.

Alas, I had to continue playing the role, in my mind, of the hopelessly-in-love ingénue who would stop at nothing until she won the heart of her leading man. We shared our last correspondence mere minutes after I’d watched Bette Davis die onscreen in Of Human Bondage, and yet I was still convinced that my relationship with James was following a screwball comedy archetype. At the time, I thought I was being quirky. I now realize I was overbearingly obsessive. I continued to send long emails. I uncovered his new AIM contact information after he changed screen names.  I even tried to buy his love the following Christmas by mailing him a gift: a CD book containing twenty favorite movies on forty Video CDs. The package, and its included letter, was opened and returned to me, minus any written response. From that moment on, I feared I was, to James, becoming the star of a different kind of film. The movie collection looked like a generous peace offering when I mailed it out. But it looked more like a threat than a gift when it was spat back at me. I trembled at the thought that James now saw me as Jessica Walter in Play Misty For Me, whereas all along I saw myself as Madonna in Who’s That Girl. Mainstream audiences clearly never appreciated the outrageous charm of Who's That Girl the way that I did. And James, clearly, did not find anything charming about my outrageous persistence.

Eighteen months after the worst Christmas gift idea of my life, I had finally purged this infatuation from my system. Prior to that, every few months I would find myself unable to resist emailing self-indulgent letters to James, letters that inevitably were really being written to/for myself.  With each letter I was deliberately inviting him to loathe me, instead of wanting him to love me. At that time in my life, the former came much easier to me than the latter, and I knew it would for James, too. I hoped we could share, if nothing else, that same contempt. As I grew to forgive and love myself for acting in such an over-the-top manner, I moved past that moment in my life, and opened the door to meeting my best friend and entering my first relationship. I don’t know if James ever did end up hating me, but I have often hoped that he forgot me.

The conclusion of my story about the young man I refer to as “James” may not be what some readers of last year’s entry had hoped for. It certainly was not what I was hoping for when I was a teenager. But today, I’m thankful for the way things turned out. In interviews collected in the book The Girl Who Walked Home Alone, Bette Davis told author Charlotte Chandler that “a watched telephone never rings”. I know that firsthand from the years I wasted as a lonely teenager relishing the role of “lonely teenager” far too much. Admitting my defeat forced me to finally acknowledge and improve upon the aspects of my personality that are adorable onscreen but destructive in real life. And, combined with my ABBA love, it gave me a unique appreciation that eventually lead to “Hung Up” becoming my favorite Madonna single of all time.

Fifteen Candles

When I was fifteen, I had a first love. And fifteen years ago today, I laid eyes on that first love for the last time. It was June 2nd, 1997, and I saw the side of his face for a split second while he was walking out of the classroom after finishing a math final exam ahead of me. We had made eye contact briefly before the exam, when I came into the classroom and caught his attention right away. I'm pretty sure it's because I was painted orange: I gave myself a spray-on tan in hopes it would make me irresistible. It didn’t. But my cartoonish appearance prompted my last glimpse of the face I associate with "first love". When he walked out, I didn't see his face, just a whoosh out of the corner of my spying eye. But I still remember what I heard in my head as he disappeared: "And that was the last time I ever saw him." The voice wasn't mine, not at that age. For years I was haunted by it, and wondered if I heard myself in the future, as though I were starring in a "Wonder Years"-ish reenactment of my life. I still don't know.

All I do know is that that voice was correct.

I've posted vintage writing about my first taste of romance to this blog twice before, in the form of a paper I wrote at twenty-one and an unsent love letter that was written when I was sixteen During the last three years of high school and throughout all of college, my unrequited teen love at an all boys' Catholic school was the most recurrent topic of my creative writing, both in and out of the classroom. This piece, written for a religion class in the 10th grade, was the first time I ever wrote about him. I wrote it as honestly as possible so that it could be a keepsake for my emotions. Then I went back and switched the gender and tweaked the details to mask my sexuality. With each paper that delved into this subject, I exerted less and less effort to hide myself. By college, there was no shame whatsoever in my creative confessionals--for better or for worse. This version presents the "honest" account, as originally written, but with the name changed to "James" as a nod to my other great unrequited love in high school: James Marsden.

I wrote this when I was sixteen years old and related way too much to Sixteen Candles. As with everything I wrote about first love at that time, the cynical thirty year old I've become can’t resist the urge to laugh at my shamelessness and naiveté. I survived middle school thanks in large part to John Hughes and Molly Ringwald. And thanks to the perfection of their first film, I spent high school waiting for my ‘Jake Ryan’ to return when I needed him most.

Bob Jeffrey 2/23/98

Value Sheet Essay

                        The Most Unforgettable Person In My Life

           

I have been fortunate enough to have a great deal of unforgettable people in my life. My parents have had a tremendous influence on me, and have loved and supported me every day of my life. I am also very close to all of my family members, and I have been blessed with many great friends. Yet the most unforgettable person in my life is someone who entered my world unexpectedly, changed my whole life, and then left as “cinematically” as he came.

I still remember the first time that I ever saw James. I was sitting in math class, feeling nervous and vulnerable because of my new setting. It was my first full week of being at St. John’s Prep, having just put behind me two painful years of Masconomet Junior High. I had lived a “social nightmare” at Masco, and my greatest fear was that because it had transformed me into this shy, insecure, almost reclusive teenager who found himself no longer trusting anyone, St. John’s would be like Masco revisited. I looked up from whatever it was that I wa doing, and I saw an absolutely beautiful person walking up to the teacher .He had short, dirty blonde hair, deep blue eyes, and soft, pouty lips. I sat there staring at him, all the while trying to make myself at least somewhat inconspicuous. I had a crush on him immediately, despite the fact that I knew nothing about him. Who knew that that beautiful, mysterious stranger would go on to become the love of my life.

I realized later that day that this “stranger” was also in my gym class. Gym was always my least favorite class, but once I learned that we were sharing the same class together, I immediately began trying my hardest to become at least somewhat athletic. I really wanted to impress him rather than come across as a scrawny little nerd who was always screwing up the game.

I began listening in math class to find out what his name was, and learned that his name was James. I saw James a lot in class and in the hallways, but never actually said anything to him. Yet I found myself noticing that we often made eye contact, and sometimes I would see him looking at me in the same “fascinated” way that I was looking at him. This seemed illogical to me since we had never actually spoken, and since I was neither attractive nor outgoing. As time went on, though , it became undeniable that we seemed to have a certain “connection” going on, just through eye contact. Then one day I was walking through an empty hallway at school when I noticed him approaching. I was nervous, but excited at the same time because I knew that this was an opportunity for me to finally converse with him. We merely said “Hey” to one another, but the word had a much deeper meaning at that moment than it ever had before. When we said it, we were staring right into one another’s eyes, and there was a certain flirtatious, almost erotic feeling in the air as if we were both madly in love with one another and knew it, yet for some incomprehensible reason we wanted to hide it. Part of this was likely fear, and part of it may have been a game of “hard-to-get”.

That greeting was definitely the spark of our friendship. Over the coming weeks, we gradually got to know each other better in Math and Gym class. Despite the fact that we were friends, I couldn’t help but be intimidated by his “social status”. James was extremely popular and well-liked, and while I wasn’t exactly unpopular anymore, I was far from being King of the Prom. James never gave me any reason to feel intimidated, though. In fact, he gave me every reason to feel anything but intimidated. Whenever I was called on in Math class and didn’t know the answer, he’d whisper it to me. Whenever I performed miserably in gym, he’d help me to do better, and he was always boosting my morale whenever I felt like I could never improve athletically. As our friendship grew, I realized that I didn’t have a crush on James. I was in love with him. It wasn’t teenage puppy love, nor was it just a sexual attraction. It was bona fide, old fashioned, true romance. I thought about him every minute of every day, I couldn’t take my eyes off of him in school, and often at night I would have dreams about professing my feelings of undying love to him. So many times before in my life I had thought that I was in love, and I probably was. Yet while the love I had felt for “the others” was real, it wasn’t true. When I saw James, I saw the man with whom I wanted to spend the rest of my life. I knew that James was, without a doubt, The One.

In spite of my feelings for James, I tried my hardest to hide my love from him. I was fearful of rejection, and feared that if I told him how I felt about him it would end our friendship. I couldn’t risk losing what I already had, and so I never revealed my love. Still, he did give me a lot of reason to think that he might feel the exact same way about me that I did about him. James was sort of a “tough kid”, and often hung around with that type of crowd. I really wasn’t, but I tried to act like I was to impress him. He was never really fazed when I would act this way, and he always treated me the same. When we would speak, he was always very kind, soft-spoken, and easygoing, which was quite different from the way that he might act with his friends. He was always very supportive and a great listener, and I still treasure the conversations that we had together. Towards the end of the year, when he joined a second semester religion class I was taking, I began to notice the reoccurrence of The Eye Game. One day in religion we were having a class discussion, and so the desks were arranged in a semi-circle. James was sitting directly across from me, and as usual I was gazing at him with every chance I got. Once again, I found that he was very often staring right back. Several times I would look up and meet his eyes. Sometimes he would look right away, other times he would wait a few seconds and keep staring. We continued this flirtatious behavior throughout the whole class, and it felt like we were both fully aware of what we were doing. Nonetheless, we never actually spoke of it.

In May of that year, I learned that James was leaving the school. To this day I don’t know why he left, but he had already had his files transferred and was set to start there in September. I was devastated when I heard him talking about this with some of his friends in religion class. Still, as always, I hid my feelings and didn’t let them know that I had even heard what they were saying.

That night, I wrote James a letter. I didn’t actually tell him that I loved him, but I did tell him that I had heard he was leaving and that I wanted to let him know that he had been an amazing friend to me that year, and that our friendship had really meant a lot to me. I left my number at the bottom of the letter, and said that I would really love to hear from him that summer if he ever got a chance. I held on to that letter for the last several weeks of school, and anxiously awaited the last day of school so that I could send it out. I didn’t want to send it out before school ended because I was worried that it would make our relationship somewhat uncomfortable in school I thought that maybe this letter would help make him realize that I loved him, or at least that it would strengthen our friendship and help to lead to something else.

The last time we spoke was about a week before school ended and our meeting was hauntingly reminiscent of our first “conversation”. It was in another empty hallway. I saw him walking towards me, only this time when he saw me, I am almost sure that I could see a smile light up across his face from ear to ear. We said that usual “Hey” to one another, only there was a certain feeling of happiness and love there that was more evident than ever. A week later, it was the last week of school, the end of that fateful year we had shared together. I walked into my first final exam, and unknowingly looked right at him. At that moment, our eyes met once again. As I was finishing my exam, I looked up just quick enough to glimpse him walking out the door, though he didn’t see me. After that day, I never saw James again.

            All summer long I waited for that fateful phone call, but never received it. I was so worried that perhaps he was offended somehow by the letter and that he hated me now and that we would never be friends again .I suppose my fears were a result of my own insecurity, for James certainly didn’t give me any reason during the year to feel this way. The three months of summer vacation went by fast, and during that whole period I never once took James off of my mind. Despite my secret devotion, I never heard from him over vacation.

            It was September 16^th, four days before my birthday. I had just gotten home from school, and my Mom told me that there was a message from “James” on the answering machine. I have several friends with that name, so I hoped and prayed that it would be The James. Before I could go to listen to the answering machine, the phone rang and my Mom answered it. She said that a “James” was on the phone but she didn’t quite pick up his last name. Immediately, I knew he had called. I nervously picked up the phone, and was immediately soothed by the sound of his voice which was as soft and gentle as it was during all of our conversations in school .He called to thank me for the letter, and we ended up talking for a half an hour about the previous year of school and about his new school and about many other things I did my best not to lead him on about my true feelings, maybe even going too far to hide exactly what I wanted so much for him to know. Nonetheless, we had a terrific conversation and that day remains to be one of the best days of my life. All that night I felt completely optimistic, teeming with child-like joy and so very, very much in love. Sadly, that was the last time that I talked to James.

            Every day since then, I have prayed that we will be reunited and that we will be together forever. I still love James more than ever, and I know that he is The One, the one with whom I want to spend the rest of my life. I went into St. John’s Prep a scared boy and came out a confident man who finally knew what love really was. James changed my life in a way that no one else ever could have, and that no one else ever will again. I don’t have a girlfriend, or a boyfriend for that matter, nor do I have much desire to have one because James is the one I love. It simply wouldn’t be fair to the other party or to myself to go out knowing that there was someone else I wanted to be with. Very few people know about James. It has always been my own secret love story, but I know that it is, in fact, a love story that is just beginning. I firmly believe that we will be together again, and that when we are, we will stay that way forever. 

May 12th, 2000: My Last Night As "Bob"

My St. John's Prep Senior Yearbook Photo

I originally intended for my blog to serve as a platform for original essays every few weeks, but a pair of important writing projects and numerous events in my life prevented that from happening. Coincidentally, I spent a lot of time this year unearthing papers that I wrote in high school and college and never expected to rediscover. Thus my blog became a virtual display case for my early work while I develop as a screenwriter. Until I have more time to devote to my blog, I share the writing that precedes everything I write about now. 

A piece that I’ve been working on since June was intended to be my final essay of the year. In it, I offer some previously withheld insight into my ambitions as a screenwriter and how this blog, my Facebook page, and my flurry of childhood videos all play into these ambitions. Ultimately, I decided to delay posting it until the beginning of the massive year Madonna has in store for us all. Madonna’s incredible career accomplishments in the second half of the 90s defined my years in high school, and fueled my incentive to succeed during a time when such a positive influence was crucially beneficial. I have many long-simmering projects ready for unveiling in 2012, and once again having Madonna’s lead to follow throughout a vital year in my own life is something for which I am most grateful. 

I offer one last “display case” essay as my thirteenth and final 2011 blog post. It deals with the unrequited gay love that I wrote about in countless papers in high school and college, one of which was posted on my blog over the summer. What makes this paper different from my previous post about the same person is that I inverted the gender of the object of my affections. I did this whenever I  wrote about him in high school, but in this final paper I made no attempt otherwise to veil the fact that I was talking about a fellow classmate at an all boys’ Catholic school. I think this defined my approach to sexuality during those four years. I never lied to myself in high school about being gay, and I shared my identity with numerous people in and out of school, but I never came out of the closet far enough to eradicate “gender swapping” from my personal essays. It disturbs me to read it now and feel like a liar, yet the deception itself takes me back to that time and place in a vivid, immediate way. It was only during that era that I called myself “Bob” instead of “Robert”. It started as a new nickname, but by the end of my years in high school “Bob” had become more like a rewritten version of myself. It took an extended stay at Emerson College to restore myself back to “Robert” in both name and spirit, but in the years since graduating I’ve funneled that personal energy into an alternate persona for my cinematic work: “Angelo de Vries”. The process of constructing that identity, and the rationale behind it, are the subject of what will be my first blog essay of 2012.

 

Robert Jeffrey 5/12/00

English IV: A, Mr. Klein: Grand Finale Paper

                                             Thoughts Frozen In Time:

                                         A Look Back at 1996 And Beyond

            Since being assigned this project, I was planning to write about my last four years on this night, the last night before my last day of high school. What a wonderful opportunity it would be to completely attack and degrade all that I so despises about St. John’s throughout the past four years. Yet this morning, as I slowly woke up and washed, I was struck with an emotion for which I had not yet braced myself: profound sadness. Sure, everyone always told me that I shouldn’t rush through high school, because I’d end up regretting it in the long run. Being the cynical old rebel that I am, I flipped the tables and made this sense of regret a benchmark to which I hoped to reach down the line. “I just want to grow up and get high school over with,” I would tell people. “That way I can be thirty-five and wonder why I didn’t do more with my youth.” Who would have thought that I wouldn’t have to wait seventeen more years?

            As I brushed my teeth and combed my hair, I couldn’t take my eyes off of my eyes. As I looked at my reflection, I was suddenly shocked by the degree of age that showed in my eyes, a sense of maturity and worldliness that had always made me so proud. It was then that I realized that so much of my life over the past four years has been continuously built on a foundation of genuine sadness and discontent. There were so many dreams that flooded my mind in elementary school, and so many nightmares manifested within the confines of junior high school. Ultimately my aspirations and reality would cancel one another out, leaving a mere shadow of the person who once was. Then love came along. I am not sure if it was a blessing or a curse that I should fall in love with my own Beautiful Stranger at the same time I started a new path of life at St. John’s Prep. I fell in love, and that void that I should have learned to fill myself was instead filled by a creature more beautiful than anything I had ever seen before. When love left my life, I did my best to cling to it. For three years I clung, but with each day that went by I slowly—VERY slowly—realized that I would never share my life with this person. That realization not only tore my heart to pieces, it also left that void empty again. Thus suffering and romantic angst would dominate my own persona and outlook on life. I was not the person I was supposed to be at the age of sixteen. Nor at the age of seventeen, and even for most of eighteen. Rather, I was a walking and talking love letter, forever sent to someone who wouldn’t, perhaps couldn’t, love me back. Thus my eyes grew old, my face grew old, and my heart grew cold. Perhaps, all along, it was really this emptiness that tainted my outlook on high school. Of course that’s not to say that high school was perfect. If it was, I am not quite repentant enough yet to admit it.

            This morning, I looked into the mirror, I cleansed my soul, and I was suddenly flooded with memories. Not the homework and the projects and the strict guidelines. Not the disappearing parking spaces or the friends who left each summer or the massive conformity movements. Instead, it was the beauty underneath all of this that filled my thoughts; the friends I had never appreciated, the people whose influence I had not acknowledged, and the one person I had to learn to let go of. These emotionally driven thoughts were rapid but wholly significant. In a matter of seconds, I finally appreciated the people who were my classmates, and realized how greatly I would be missing them in a matter of hours.

            From there, my mind became less focused on what happened on the St. John’s campus. Instead, my world briefly became a supernova of thoughts and dreams and milestones, all of which were given birth to while I was in high school. I remembered lying on the floor of a hotel room in Disney World during April Vacation of 1997. The Spice Girls were enjoying concurrent chartbusters with “Wannabe” and “Say You’ll Be There”. Every ten minutes there was another TV spot for Romy and Michelle’s High School Reunion. Box office analysts were astounded that a little slasher movie called Scream was continuing to dominate the box office some four months after its initial release. I flashed forward a year, to Brother Borgia’s sophomore math class. The Spice Girls were vanishing from the pop culture landscape upon which they had made such a seemingly indelible impression. “Romy and Michelle” was enjoying a fruitful second life on video after having performed disappointingly in theaters. Scream 2 was only a matter of weeks away, and EVERYONE was practically in line.

            The memories kept flooding in their deliriously non-linear fashion. I was scanning through a bookshelf at the mall in January of 1997, when I stumbled upon a little paperback book I had never heard of before. The book was called “Pretty in Pink: The Golden Age of Teenage Movies”, and for the rest of Freshman year it would become a second Bible to me. Its affectionate  assessment of the high school films of the 80s sparked in me a whole new realm of fantasy. How wonderful it would be to be a high school student at a time when pop culture was shaped around teenagers. The closest that the Class of 2000 had were the films Clueless and the newly released Scream, and these were only two films spread apart by eighteen months. That hardly defined an era. Then it was August of 1998. I sat in the smoking lounge of O’Hare Airport with my father explaining my concern that the teen genre would burn out again as a result of too many similar films being released.

            Yet it is the most secretive and mysterious aspect of my life that I consider my most defining moment throughout this whole era. “She” has been reincarnated so many times in my writing projects and film ideas that, at times, I almost forget who it was that I originally fell in love with. Yet I will never forget her. Perhaps she is the “Jenny” to my “Oliver”, the one true love whom I have to thank for all of the joy and inspiration in my life. Or maybe she was really the Bette Davis interpretation of “Mildred” in Of Human Bondage; a force so destructive and demystifying that she would forever seal my fate, if only through crimes of the heart. All I really know is that, when I look back on the past four years of my life, it is her face that I will always see. She was the star of the film that was my life while I attended St. John’s. It is she whom I have to thank for both my strength and detachment. I may never see her again in person. For all I know, even the faintest glimmer of romance was never meant to be. Yet for four years she has lived on in my heart, and has become, somehow, subconsciously linked with my experience at St. John’s. Every time I look up to the spire or walk past students waiting for a teacher to arrive, I see her face. When I glance at the bulletin board or check a book out from the library, I hear her voice. And when I say good bye to St. John’s Prep on May 21, 2000, I say goodbye…to Her.

I wrote this essay as a final assignment for a great teacher: Mr. Klein. I have applied a few of Mr. Klein’s grammatical fixes to appease my post-collegiate cringing, but this is still 99% identical to what was originally written. I have only the vaguest recollection of writing this essay, but I vividly recall his comments on the last page. I won’t reveal what he wrote, but I will say that in a short statement he instilled in me a tremendous sense of confidence and optimism that had a truly profound impact on my life ever since. Prior to that last day of class, I had looked at Mr. Klein’s English class the same way I looked at every class in high school: as a vehicle for my expansion as a writer. I was not a great student, and not least of all because I was one of those types who only ever read Cliffs Notes. But my writing apparently made some small impact on my teacher, enough for him to see me off to life after high school with an encouragement that I have held close ever since.

Confessions of a Teenager In Love

I recently unearthed a love letter that I wrote to a straight classmate in June 1998. I never sent it, and for years the letter has been a hidden chapter in my body of work. It is just as pure, and every bit as Madonna-influenced, as the “Vogue” video of myself as a nine year old. But this moment-made-public, unlike the “Vogue” video, was a work of pop art only ever intended for an audience of one. It is the ultimate proof of how madly in love I was at the age of sixteen. 

The object of my unrequited affection was briefly my classmate at an all boys’ Catholic high school. He left after our first year, and I spent the next three being hopelessly in love. I’ll call this person “James” because James Marsden looked so much like him back then that I formed a massive, “Vertigo”-esque crush on the actor. I wrote “my James” a heavily coded letter after he left, telling him what a great friend he was. But the letter below, written one year later, was meant to completely, and shamelessly, express the depth of my devotion. It’s sweet, hilarious, painful, and cringe-inducing in its lack of cynicism—a perfect time capsule of my summer as a sixteen year old. 

I changed the names of people, but not locations, and omitted only a few sentences that referenced a mutual friend. I’ve left it otherwise intact, including grammatical errors and internalized homophobia.

Hey James! This is Rob Jeffrey—again!! I know how weird this must be for me to be sending you another letter, but the reason I am writing again is because there was something I tried to get across in the last letter, but was a little too afraid to do. I realize that while we got along in school and talked to each other and all that, we never really hung around together very often. But what you may not know is that you actually played a much, much bigger role in my life while you were at SJP and after you left than you might have expected. Since you play such a huge role in my life, I think that you deserve to know a LOT more about me. So I decided to confess everything to you in this letter. The reason that I am using this paragraph as a “cover page” is to warn you about the content of this letter. The letter is very bold and upfront, and while I have tried not to make it too threatening, there is the potential that you will be offended by what I have to say. I just hope that you won’t see me as an enemy once you’ve read my letter. What I am going to tell you could shock the hell out of you, but no matter what your reaction is, my only request is that you please keep an open mind, try not to be too intimidated by what I have to say, and also that you read the whole letter through to the end.

              Okay, here’s the first bombshell: I’m gay. I don’t like to use those words, because I don’t really think of myself as “being gay” since it differentiates me from so many people, and because frankly it doesn’t play THAT big a role in my life. I have never come out in person to the people close to me, I just try to let them know without actually saying the words. I wasn’t planning on telling you all that, but I suppose it’s necessary that you know up front before you read what I have to say to you.

                Now, here’s the REAL bombshell: I Love You James. I have loved you since the first time I laid eyes on you in Miss Hill’s class on the 2nd day of school, and I have loved you more and more with each passing day since. Ever since I first spoke with you I have wanted so bad to tell you the way I feel, but rather than confess, I went the other direction and did everything in my power to keep you from knowing my Secret.

      I think that in the back of my mind I thought that one way or another you would know by the time that high school was over that I loved you, but when I found out you were transferring to a different school, I figured that I would never have the chance. That’s why I sent you the letter last summer. I hoped that you would somehow realize after reading the letter that I was in love with you, and that sending the letter would somehow bring about a fairy tale ending. All summer long I waited for that fateful phone call from you, hoping and praying that you would call and tell me that you loved me too, and that we’d live happily ever after. Believe me, I KNOW how fairy-ish that sounds, but as I found out, I guess I’m just a sucker when it comes to love.

                By the time school started, I’d pretty much given up hope on that phone call. Then, four days before my 16th, birthday, you called. I can still remember so vividly the sound of your voice that day, and how overjoyed I was to hear it. I couldn’t even think of anything even remotely intelligent to say, because I was so nervous and obsessed with sounding cool on the phone so that I’d impress you. Yet coming off of that phone call, I felt so happy and relieved and unbelievably optimistic. That day still remains one of the greatest days of my life, and definitely the happiest day of Sophomore year. Unfortunately, the days that would follow would not be so happy.

                The 10th grade was a long year for me James, not just because it was so academically difficult, but because I was living my life without my one true love. It was bad enough to be alone in that situation, but what made it all worse was that I felt like I could and should tell that person that I loved him, and yet I was too chicken to go through with it. James I have loved you since the beginning of Freshman year, and for the past 18 months I have devoted my life to keeping those feelings a secret from you. But this secret is literally eating me alive. During the year I spent most of my time after school just working on my homework, and on weekends I stopped going out. I would just sit up in my room watching TV and listening to Madonna, hoping and praying that our paths would cross. I had the power to change all of that, and yet I didn’t. For some off the wall reason I had and still have myself convinced that suffering the way I did and the way I am now is better than being rejected by you.

                By now I am sure you have heard the song “Frozen”, and that song is the best way to describe not only my feelings for you, but also my own emotional state since you left SJP. When Madonna is singing that song to her “lover”, it sounds as if I was singing to you. It perfectly embodies my feelings of “terminal yearning” for you, my burning desire for you to “open your heart to me”. Yet at the same time it also describes my own state of being “emotionally frozen”, which has resulted from the absence of love in my life, the absence of your love in my life.

                So many nights I have wondered what point there even was to living. I have been so unhappy, all because of my own fear and insecurity, and I just had no motivation to go on if this was what my life was going to be like. My only real mission which had yet to be accomplished was that I still hadn’t  told you I loved you. I don’t know if you ever saw Dick Tracy, but there is a scene in that movie which is without a doubt one of the most significant pieces of cinema I have ever had the opportunity to see. At the end of the movie, Madonna’s character, Breathless Mahoney, has just been shot, and as she is dying Dick Tracy holds her in his arms. She looks up at him and says “Tell me the truth, could it ever have happened between us?” He didn’t answer, and then Madonna leaned up and kissed him, before closing her eyes and dying. I know how insane this is going to sound, but oftentimes I would think that being in this situation would be the only chance I might have to tell you how I really felt. If I was minutes away from death, and I told you I loved you, then I wouldn’t really have to worry about your potential anger, I wouldn’t have to worry about the taunting and discrimination which could arise from my confession, because I wouldn’t live to suffer it. There were times when I even hoped that I would end up in that situation, of being near death, because I thought that that was the only situation where I would be forced to tell you I loved you, since I would no longer have the “luxury” of hiding it from you for any longer. I realize how mental that sounds, and the fact that I’m telling you must seem even more bizarre, but my reason for telling you is to demonstrate just how much I wanted you to know that I loved you, and also how hard it was for me to actually say those words.

                Every time I see a movie that is even remotely romantic, it immediately makes me think of you. It doesn’t just make me think of you because of the romance in the movie, but because I feel like these are the movies which I should be watching WITH you. There are so many movies which I wish I’d watched with you, so many songs I Wish I could have listened to with you. It truly terrifies me to think there are people who I go to school with now, who I barely even talked to last year, who know more about me than you did. I want you to know everything. I want to give you everything. I just want to open my heart to you and tell you everything that’s on my mind, because I think that you should know me better than anyone else in the world. I feel that I owe that to you. I know that all this must sound TOTALLY psychotic and now I am worried about you being scared more than anything else. I am not trying to put all of this crazy shit on your shoulders. I’m just trying to fully express myself to you, because I do feel that you deserve to know what an important role you’ve always played in my life, and just how much I truly love you.

                I can still remember, way back in December, sitting in a movie theater and watching Titanic. Throughout the whole film, I could see parallels between what was happening onscreen with what had happened off screen in my own life. During the movie, I found myself being able to relate to the character of Rose, some one who essentially performed throughout her whole life, playing a role she didn’t want to be playing. Yet then Rose was saved by Jack, who brought her liveliness and joy, and who basically brought Rose back to life. That’s what you did for me James. I went into SJP determined not to bet eh same person I was at Masco, bur rather to be an altar ego who I had created. Everyone used me and treated me like I was worthless when I went to Masconomet Junior High. I decided to just give up being The Nice Kid and do my best to be the most popular and powerful person in the grade. I was so consumed by self-loathing that I no longer wanted to be Robert, which is part of the reason tha I changed my name to Bob, and the whole reason that every step I took, every word I uttered, was completely calculated. I was obsessed with impressing every single student and becoming the person who I thought I wanted to be, as opposed to being myself. I also think that I had unconsciously given up on love, because ultimately I wanted for popularity to be my own substitute for love. It all could have worked out, but as Madonna said in Dick Tracy, “You were my only mistake.” The one obstacle I had never counted on was falling in love. For some reason, it never came into my mind, until I found you.

                No one ever treated me the way you did James. I had seen so many movies with characters that had traces of you, and I always wanted to find some one like that as a friend or even a lover, but after years of friends who either never quite understood me or just used me for various reasons, I had pretty much given up on finding that person. Yet after only a few weeks of knowing you, my whole life was filled with romance and passion. I know how strange that is considering I wasn’t even ‘with” anyone, but whereas my goals in the past had all been based upon fame and fortune and success, after you walked into my world, I realized that all I could ever need was your love.

                While I am certainly not accusing you of anything, I would be lying to say that there were not times during Freshman year when I thought that you might share the same feelings for me that I had for you. Part of my reason for thinking that you might love me too was that you were the only person I have EVER met who could see through all the bullshit, who looked past my many masks and performances and actually saw The Real Me. It seems that in my life, particularly at St. John’s, I was always performing, always trying to make myself into everyone’s individual fantasy. It got so bad that when people would say to Be Yourself, I would panic, because I didn’t know who that was anymore. Yet not only did you ignore the walls I put up and show me what it meant to “be myself”, but you actually respected and cared for who I really am. You touched me in a way that no one else ever could, and that no one else ever will. At the same time, I also felt like I was seeing through you in a way that few people probably have. I got the impression that maybe not too many people told you what a wonderful human bein you are James. I know that you have a certain “image” which is sort of a cross between a 1950s “bad boy” and a mischievous, affable, class clown type. Yet after the conversations I had with you, and after seeing the way you treated your friends and listening to the questions you asked in religion class, I could see beneath your image that you were a much more complex person than I might have originally thought you were. I saw a person who was innocent, vulnerable, deep, kind, caring, and just the type of decent guy who’d give you the shirt off his back. When you were with me, that was the way you acted, and that’s the person who I fell in love with.

                I am not going to lie to you James. I want so bad for you to love me back the way that I love you, but if you don’t I’ll understand completely. I think that at this point what I need is closure. I just have to know whether or not I have a chance with you, whether or not I should keep waiting for you to tell me you love me. I know how strong that may sound, but I have to stop apologizing for being in love with you, and just bare my soul to you. Like I said before, I think you deserve that. If you don’t want that relationship, though, I hope that we can be better friends than we are now James. You have played such a significant role in my life, and I hope that we can at least maintain a friendship. I promise that I would never let my romantic feelings come between us. I was in love with you for the entire Freshman year, and I think I did a pretty good job of hiding it from you back then. If necessary, I’m sure I can do it all over again.

                I thought you deserved to know how I really felt about you all along, and now you do. Even if this letter were to completely destroy any trace of a friendship that we had already, at least I got the chance to tell you what an extraordinary human being you are. Something tells me that not many people have told you that you’ve changed their lives and that they think you are an incredible person. I’ll be a whole lot of people have felt this way about you, but even if they haven’t, I sure as hell did, and I still do. Corny as it may sound, the world would be a much better place if there were more people like you. When I first went into St. John’s, I was so shy and gawky and had “Unpopular” written all over me. Yet you still treated me like I was your friend, and for that alone I am eternally grateful. You didn’t boost my confidence. You GAVE me confidence, something that I had never, ever had before. And that is only one, early example of the many great things you did for me. You are so kind and admirable, James, and you deserve to know it, even if it’s in an otherwise potentially offensive letter.

                If you find, after reading this letter, that you absolutely hate me and want nothing to do with me, I would ask that you not tell anyone my “secret”. I have yet to come out to my close friends, family, and even my parents, and no one at SJP knows that I’m gay. My point is, if you are really angry about this letter, I’d ask that you not tell anyone about it. I realize just how self-absorbed that is, but I’m pretty terrified about what would happen if my secret got out. Still, if you did tell everyone, I would have to accept that, because by sending out this letter to you I am taking that risk. I don’t think, knowing the type of person you are, that you would do that, but nonetheless, I must be prepared for the worst.

                James, I cannot begin to describe just how frightened I am about sending out this letter to you. I can barely even type it, because my hands are trembling at the keyboard. As much as I have wanted to tell you all of this, I’ve also wanted to play it safe for the rest of my life and keep all of this information hidden from you. That’s why I wanted for you to call me and tell me that YOU felt this way about ME, because I didn’t have the guts to tell you my feelings. Frankly, I still don’t. But I figured that somewhere down the line I would not be able to keep it a secret any longer and would just have to tell you. Rather than wait for years until I had that courage, I figured that for eth first time in my life I would take a risk and just act on impulse. I have been working on this letter for months, but I was never really all that serious about sending it, because I never thought I’d have the bravery to go through with it. Then, at 1 AM this morning, when I was tired and didn’t think quite as “objectively” as I do when I’m more awake, I decided that I would just say “What the hell” and send it to you.

                As much as I would love for you to call me and tell me, after reading this letter, that you feel the same way, I am not expecting for that to happen. As a matter of fact, I am expecting quite the opposite. I once heard a quote which state, “If you love some one, so much that you can hardly breathe, then that person just has to love you back.” Since I was so very, very much in love with you at St. John’s, I would often interpret certain things which you said or did as a sign that this quote was, in fact, the truth. I know that that may sound stupid, but I guess I’m just a pretty gullible person, because although my wish might come true, in all honesty I doubt that it will. Despite the fact that I sometimes thought you might “like” me, you never gave me any reason to think that you were gay. I just hope that you won’t hate me after reading this letter, and that you won’t see me as some kind of a threat to you because I’m gay. The reason, as I stated before, that I am so nonchalant about being in love with someone who happens to be male is because I hardly ever consider myself “gay”. I don’t like to be categorized, and therefore I don’t often categorize myself. My point is that I hope my candidness is not too intimidating about being in love with you is not too intimidating, and that you won’t think I’m some kind of a weirdo for telling you all of this.

                I know all of this must be pretty heavy for you James, and if you are reading this sentence, I think you deserve to be thanked for reading through to the end. In my original draft of this letter, I wrote in the last paragraph that no matter how you felt after reading this, that I’d really like for you to call me to tell me what your reaction was. Although I still would like for you to let me know how you reacted, the fact of the matter is that now that I am actually preparing to send out this letter, I’m rapidly becoming 100% chicken shit, and therefore I’m pretty damn scared about your reaction. What I’m trying to say is that if you are upset about this or really don’t want to talk about it, please don’t fell that you have to contact me right away. In fact, if you don’t ever want to talk to me again, it probably would be better if you didn’t call at all. But if you aren’t that upset, and don’t completely hate my guts, then I would really like to hear from you. Even if you are calling to say that you aren’t gay or just “don’t like me that way”, which I assume will be the case, or if by some chance you really DO feel the same way about me, then I really do need to hear from you. During the past year, my thoughts have almost always been concerning “what could have been” and “what might still be”, so at this point what I need more than anything else in my life is closure. I want to start my life again, and while it’s a LOT to ask for, I need to know whether or not you are going to be a part of it. Even if we just became good friends, that would be enough for me. You are a great person James, and anyone who has you in their life is truly blessed.

                If you would like to get in touch with you after reading this, my telephone number is (978) XXX-XXXX, and my beeper # is (781) XXX-XXXX. My e-mail address is XXXXX@aol.com, and my postal address is on the back of this envelope. If you would like to talk to me, please get in touch via whatever is the easiest and most convenient form of communication for you. Please don’t feel that you have to do it very soon, or that you even have to do it at all. What is important to me is that you know all of this, and now that you do, my mission in life is accomplished. I guess all I have left to do now is meet Madonna J Thanks again for everything James, and no matter what happens in our futures and regardless of whether or not we’ll ever talk or see each other again, I wish you the very best in life.

                                                                                                 

Sincerely,

                                                                                                                Bob Jeffrey

I spent hours writing this epic letter at the family computer before I was prevented from sending it by my parents, who figured out I was off to send a love letter to a straight male. I saw myself as the Juliet to James’s Romeo, initially, but was soon quite relieved: I came out to my parents that night, and the response of warmth and unconditional love was truly as ideal as any gay son could ever hope to receive. Far from forbidding me to be in love with another man, they were keeping me from giving my emotions to the wrong kind of man, and potentially paying a bigger price than I could ever have foreseen. At nearly twice the age I was when I wrote this, I shudder to think of the consequences such a confessional could have had in 1998 outside of my enlightened universe of Massachusetts. This was, after all, mere months before the murder of Matthew Shepard.

Of course, James never read this. In fact, for over thirteen years, no one has. Now I think it’s time it was sent out to the world. It’s hard to fathom that I thought a straight sixteen year old male would fall in love with the writer of this letter, but I admire my younger self for believing that. For all its shamelessness and self-absorption, the vulnerability on display is painfully familiar to anyone who has ever been in love with a person whose sexual orientation was not compatible with their own.