Dear Caroline,



We are delighted to inform you that the Committee on Admissions has voted to offer you a place in the Gilford Academy Class of 2016! Nearly fifteen thousand students applied for admission to the entering class, making it the most competitive, qualified, and Anglo-Saxon applicant pool in Gilford history.

However, as you prepare for the transition to boarding school, we suggest you look over the following materials very carefully. The zip code, middle school, and surname listed on your application suggest that you won’t fit in otherwise and we want your adjustment to life at the Academy to be as seamless as possible. Enclosed you will find everything you need to make your time at Gilford unforgettable and your middle-class upbringing unnoticeable. Congratulations on your acceptance and we wish you a warm welcome to the Academy.



Understand and make peace with the fact that the nicknames here are absurd: Binky (Barbara), Topper (Christopher), and Trip (as in the III, triple) will be among the people you meet during Freshman Orientation. Learn to count to at least five in Roman numerals.



You will hear many stories about a place called Dalton. Certain people may be “from Dalton,” but this is not a city—it’s a school. Similarly, Collegiate is not an upscale rehab center and Spence is not an insane asylum for very thin girls. Do not ask anyone where these places are.



Although you made it through 8th grade with almost no physical activity, this will change at Gilford. We highly suggest that you don’t follow your first impulse and sign up for Squash just because you think the name is funny. Squash involves a racket and you will be a menace to your peers.



Because you’ll send Tattie (Theodora) van der Venter II to the Health Center with a bloody nose, your only chance of becoming popular will be by dating senior boys. This process will go significantly more smoothly if you resist the urge to ask why anyone wearing that much outdoor performance gear would also be wearing boating shoes.



When you become concerned that your new boyfriend has a fetish for making out in public—don’t be! Places where it is okay to be intimate at a boarding school: empty classrooms, the observatory, the library, the rare books library, the music library, the science labs, the greenhouse, the athletic fields, the chapel, etc. Places where it is not okay to be intimate at boarding school: bedrooms.



Tell your parents upfront about the bills they will receive from the campus grill. Explain to them that consuming Diet Coke is a social ritual and that to be cokeless is to be friendless. This statement will hold true for a wide variety of situations.

Do not tell your parents about how frequently you and your friends charge new uniforms at the bookstore simply because you are running late to Squash practice. They will not understand. Instead, use this phone call to brief for Parents Weekend. Calmly explain to your mother that your roommate is allergic to flannel, and to your father that he will be too ill to travel. Copy and paste the school dress code into the body of an email. Find: “students.” Replace: “parents.”



While shepherding your parents around campus, your mother will point and stare openly at the second-wives. You father will be not-ill.

As fall peaks in New England, everyone will talk about The Game. Don’t be alarmed by its ominous vagueness or what sounds like the world’s most dangerous pep rally: a large, student-organized bonfire. We suggest that you use these final weeks of your first trimester to get a head start on studying for your exams and buying Adderall while the demand is still recreational and low.

When you return from Thanksgiving break with new clothes, everyone will notice and be impressed except for Tattie van der Venter II, who is still upset and is clearly an incorrigible bitch. We, The Committee on Admissions, strongly encourage you to steal her boyfriend in order to help Tattie become a more well-rounded person.



Your new boyfriend will be very attractive. So attractive that you will be able to overlook the fact that he uses seasons as verbs, says things like “money’s just a way of keeping score,” and corrects your pronunciation of Hermès. When he invites you on the seniors’ trip to Aspen: accept. It is never to late too fake a knee injury. Quietly google “Aspen what to pack.”



During this powdery, hormone-heavy week, you will learn a lot about geography. For example, Porto Ercole is the natural stopping point when one is sailing from St. Tropez to Capri; North and West do not exist in the Hamptons; Sun Valley is oddly full of snow; Locust Valley is not the hellish dump it sounds like.



When you return to school in January you will feel like everyone is tanner than you. You have failed to grasp the spirit of Christmas vacation: skiing, then Florida. However, a number of your New York friends will be pasty too, as they will have spent “the season” in “the City.” Resist the urge to say you enjoyed “the extra time” at “Home.”



In February the weather will turn cripplingly cold and everyone will get depression or an eating disorder, except for you who’ll catch the flu. The Health Center will be prisonlike and fun. Things the nurses will bring you if you ask: your assignments, buttered toast, magazines, cake, your mail, a laptop. Things the nurses will not let you do: leave.



As the campus thaws, there will come a sharp and unannounced change in style. In the morning, we highly recommend you think of yourself not as a young woman dressing for class, but as an Episcopalian about to board a boat to a horse race.



When your boyfriend starts pressuring you for sex, be open to the possibility that he sucks. The Committee on Admissions regrets to inform you that you need to dump him and move on.



Over spring break in Harbour Island, you will impress friends with your knowledge of golf by talking about it a lot and by not actually picking up any items that are golf-related. As Tattie once said, you have the hand-eye coordination of a three-year-old and do not know your own strength.



Upon returning to school, there will be only a short amount of time to study for exams. Adderall will be expensive and everywhere. Your friends will complain alternately about work and sleep, however, refrain from giving them a pep talk. Instead, offer sympathy: “You work so hard.” “Wow, it seems like every time I see you you’re awake.” Ask for Adderall.



After exams, life at the Academy will shift dramatically towards summer. For one grassy, golden week you will sit on lawns and discuss the world in definite articles: The Vineyard, The Riviera, The Cape, etc. You will learn precise connotational differences between St. Michaels (boots, ducks) and Newport (hats, Kennedys). “Regatta,” “au pair,” and “Cap d’Antibes” will enter your vocabulary without you ever knowing how to read or write them. You are a first generation immigrant.



Purposely tell you parents that Freshman Check-Out begins eight hours later than it actually does. When your Dorm Head asks you where your parents are, do not say that they forgot you. She will respond to this situation seriously. When they finally arrive at dusk, you will be packed, the second wives gone, and the wood-paneled station wagon just as shabby as you remembered. Your parents will be beaming and still following the dress code.



We hope that this material has been helpful and that you will decide to join us this fall at Gilford. The resources and experiences that the Academy offers are unparalleled, and we are confident that you will find ways to take advantage of them. Alternatively, classes will be held from 8:00 AM – 3:00 PM, Monday through Friday. Whatever your decision may be, The Committee on Admissions wishes you every future success in your formal education and beyond.



Sincerely,

The Committee on Admissions

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Caroline Calloway is a graduate of Phillips Exeter Academy and currently studies in New York City, where she continues to live beyond her means.