1985
Dear admirer,
Thank you for your application for the position of My First Girlfriend. Unfortunately, for some reason not even apparent to myself, I will end up finishing elementary school a bachelor, remembered forever by the girls (and likely some boys) because I wore a black leather jacket—and wore it well—in the motherfucking 5th grade.
Sincerely,
G.M.
1986
Dear applicant,
I appreciate your interest in me—particularly my vast collection of Guess jeans which accentuate my cute little butt (by all accounts) so well. Unfortunately (for you), your friend Denise is much more mature, already nearing a B cup while you are still between a triple-A and a double-A. So, I’m gonna go with her instead—even though she won’t let me do anything except hold her hand, at which point I’ll dump her for someone else.
Good luck,
J.H.
1988
Dear contender,
Despite how attractive I found you and despite our hours-long conversations sitting on the logs at the campfire circle, I’ve decided to go in a different direction. The dufuses in my cabin made a bet on getting to second base with Cara, and I really want to beat them. By the end of the summer, having achieved my goal, I’ll regret not pursuing you instead, as I will recount to Jenny, who will recount to you in a letter months later. Unfortunately, camp is over, and I’m headed back to Chicago and will never see you again.
Affectionately,
G.C.
1990
Dear candidate,
I’m sorry to hear that you regret turning away when I tried to kiss you that day after school when we sat on your seafoam green bedroom carpet, knees touching. I had no idea you hadn’t been kissed before and were just nervous because you liked me so much. Unfortunately, you never actually told me that, so I just felt like dumbass. I’m a sex-crazed 15-year-old boy who doesn’t have time to figure out what girls are thinking. So, I’m just going to move on to that girl rumored to give out blowjobs like candy.
Sorry,
L.M.
1992
Dear petitioner,
I was shocked to get your letter and hear that you were interested in the position of being my girlfriend. Even though you invited me to prom and at every party, we’d end up alone together in some corner, chatting for hours, and I touch you all the time, it never occurred to me that you might think of me romantically. Coincidentally (and unfortunately, as it turns out), I’ll end up at the same small college as you and continue to string you along—taking naps with you, putting my arm around you when we’re out together—for one more year until you finally decide you’re tired of being gas-lit, by which point I’ll drop out of school anyway, leaving you disappointed that you had no chance to tell me to go fuck myself.
My half-hearted apologies,
A.B.
1994
Dear claimant,
I was so honored to be your First Boyfriend. I appreciate the two years of your life you invested in our relationship—especially given, as you point out, that it took a while for you to come around after I rather aggressively pursued you. I realize the irony here, given that I now have to end things because, as it turns out, I’m gay, something I’ve actually known about myself for a long time. I’m also sorry I made your first experiences with sex terrible—though whether this can be chalked up to my sexual preference or my pure narcissism is unclear. I assure you that these two years have meant a lot to me, too. We had so many great times—like all those times in bed where you lay there waiting for something to happen and I just wanted to sleep. You were so great to sleep next to. Anyway, I’m glad we’re still friends.
Love,
K.F.
1999
Dear claimant,
I know I sent you an email only two days ago telling you I missed you terribly. And I know that only a month ago, I called you my girlfriend for the first time. And I know that when your recently ex-boyfriend visited, and our relationship was still unclassified, I begged you, with tears in my eyes, not to sleep with him. But that writer’s conference I went to? The one that started the first week of classes, so you covered mine for me? Yeah, it was all so romantic what with everyone being writers and all, and one night, I locked eyes with a girl, and I knew she was the one and so I’m sorry, it’s over between us. Tomorrow I’ll move out of the apartment across from yours—you’ll walk out your door, look across the courtyard and see my blinds drawn wide open to reveal a completely empty apartment. This may strike you as harsh but as you know, I’m prone to dramatic gestures and I just couldn’t resist leaving our relationship with a flourish. In the meantime, I need a ride home from the airport. Do you think you could come and get me?
Sorry.
M.N.
2001
Dear claimant,
This is so hard for me because I really, really like you. I know I flew across the country to visit you—twice—with money I didn’t have, and that might have given you the impression we would continue. But it turns out I need to get married soon and given that you’re unmistakably gentile, I could never marry you. I know you weren’t thinking about marriage at all—you mostly liked me for my looks and because you were on the rebound from some asshole—but I was. Sorry I never told you. Sorry I wasted your time. And sorry I dumped you a month after your dad dropped dead of a massive stroke. Yeah, really sorry about that.
Love,
J.G.
2002
Dear inquirer,
I understand your frustration with my ghosting you. And I appreciate your call, which forced me to be honest with you—since I lack the balls to do it myself. It’s just that I found someone that I have a real connection with—not just our current arrangement of me taking you out to dinner because you’re subsisting on an adjunct salary and then going back to my condo that can’t possibly have been bought on a teacher’s salary and having sex. I’m a financier at heart (you can take the boy out of Boca…) and with you, my return on investment was looking a little dicey. Though I know you’ll miss the free dinners, it’s probably time we both cut our losses. In a year, I’ll undoubtedly quit my job, move to a wealthy suburb, day trade full-time, and become a libertarian.
Good luck,
F.L.
2003
Dear inquirer,
Sorry I went AWOL for a couple weeks after we were seeing each other regularly for two months. And sorry that, after those two weeks, I left you a bunch of drunk voicemails impersonating my cat, Walter. I don’t really know how to express myself with things like this. Frankly, I just can’t really do relationships. Which is undoubtedly why I do stand-up comedy and drink to excess.
Sorry about that,
A.D.
2004
Dear inquirer,
Please accept my apologies for sending you mixed messages for months. I, too, enjoyed those nights we talked for hours at the bar about writing and teaching, nights that inevitably ended with us standing at our respective cars saying awkward goodbyes, as if we both expected something else to happen. But to be honest, I’m not sure if I want to date you—or anyone, for that matter, at least not right now. I like to think of myself as a brilliant, brooding Irish Catholic writer, à la James Joyce, but maybe I’m (also?) a textbook Irish-Catholic son-of-an-alcoholic neurotic filled with self-loathing who doesn’t know what he wants. You should probably go with that other guy who’s paying a lot of attention to you. I sense you’re coming to the end of your rope with guys who don’t know what they want. That guy seems to know.
You deserve better,
C.P.
