Letter Man - The American Spectator | USA News and Politics
Letter Man

In the bottom drawer of my bedside table, you will find, if you care to look, dozens of intricately folded pieces of paper, almost all of them from the early post-Cold War era. They are what the French call billets-doux, what you might call love letters, and what I call “proof that I was awesome in middle school.” Why do I keep them? Because I find it difficult to throw away anything containing the phrase “you’re sexy,” especially if it’s written by a girl and addressed to me.

After stumbling upon these old letters at my mother’s house last year, I transported them to my apartment in Washington, D.C., where I can read them whenever I feel nostalgic or vain. Which is all the time.

These letters, you see, are a history of my adolescence. It is a history of which I am exceedingly proud. What are for many people the most awkward years in life were, for me, my glory years. I was at my social peak—popular, good-looking, and obsessed with being popular and good-looking. Thanks to these letters, you don’t have to take my word for it.

When it came to written correspondence back then, my policy was proactive. In much the same way that President Obama “asks” the rich to pay more in taxes, I would ask—i.e., order—my female classmates to write me letters. They could write about any topic so long as the topic pertained to me. More often than not, the results were gratifying.

“You’re sooooo sexy,” writes a girl with excellent taste and terrible spelling. Dominique, after noting my “good buns,” writes, “I can’t think of anything more to say.” My buns left her speechless. The words “stud” and “hunk” are prevalent, and with good reason—because they describe me accurately, and because I insisted on them.

Not all of the letters are sufficiently complimentary. Sarah scribbles, “I ♥ Ray you!” Ali confesses, “I used to think that you were the hottest thing on earth but…” These are the letters I tend to ignore.

My ex-girlfriend Ashley writes multiple letters asking if I’m going to “the dance.” She informs me that two guys asked her and she said no to both “because I really like you.” (Understandable.) Then she plays the pity card: “When I do go to the dance, I’ll probably sit over in the corner the whole time during the slow songs.” If I remember correctly, that is precisely what she did.

A girl from another school whom I’ve never met writes—and mails—me a letter, which is both flattering and weird. “I am NOT a stalker,” she claims. “On the contrary, I consider myself to be blunt and emotional.” This is the end of our correspondence.

My type of girl does not write in all caps. My type of girl heaps praise on me constantly, and she uses tongue. Kristin is proficient in both areas. In a letter to her friend Stella that I somehow intercepted, she confides, “I don’t love Windsor anymore because he’s so hateful to me.” Four sentences later: “There’s just something about him that I love so much.” What Kristin lacks in consistency she makes up for with infatuation.

Here, from Kristin, is a handwritten list of 67 things she loves about me. There are several repeats. She lists “butt” 15 times and “brain” once, which both delights and disturbs me. Also on the list are “hands” (three times) and “arm.” So, according to Kristin, I have three hands, one arm, and a butt 15 times more lovable than my brain. I am one of a kind.

Emily, my subsequent girlfriend, isn’t as adept at itemizing her love. In one letter, she says she loves me in “101 ways,” which is nice but, unlike Kristin, she doesn’t provide a list of them. Later, she atones for this egregious mistake by writing the phrase “I love Windsor” 99 times, though not in calligraphy. Our relationship would end tragically (for her), as she makes clear in the following letter (edited for space, legibility, and family values):


Thanks for being [an anus] to me yesterday. Why did you put me through that [poop]? … Why didn’t you just break up with me instead of hurting me a lot? … Yesterday when I saw you sitting with Sarah and all of them, you killed me. I loved you, but I wonder if you loved me at all. You broke my heart. I hate you for that…. That’s all I wanted to say before I kicked your [fanny] to hell.


I took this to mean, “Let’s break up” and “you’re sexy.”

Another note I find is from Dr. Schmidt, who taught me U.S. history in high school. Reviewing my performance in his class, he commends my effort, praises my paper on Iwo Jima, and concludes, “What Windsor does lack is an interesting style of writing. At the moment, it is unimaginative and unvaried. But knowing Windsor, he will work on it!” If only he could see me now, at age 33, “working” on my writing by scrutinizing the scribblings of 12-year-old girls from 1991-94—which is to say, from U.S. history. 

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