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.
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.