I’m not sure I’ll ever really feel like a person who graduated from a New England boarding school. There’s too much that made me feel somehow set apart from my classmates. “Preppy” has never been a word that accurately describes me, and that was the first hurdle I faced when trying to fit in. I had zero school spirit, and did not care to develop any. I had comic books delivered to my mailbox weekly. I applied to exactly one Ivy League university. I, along with one other girl, was the first graduate to attend Oberlin College — the polar opposite of a boarding school experience! — in over a decade. Oh, and in my school’s 100+-year history, I was the first Black student to graduate as a direct legacy — something white students had been doing for decades.

Our ten-year reunion, which I began stressing about approximately a year ago, takes place in May. I haven’t really kept in touch with many people from my class, and went nearly a decade without seeing the best friend with whom I decorated my yearbook page. My other closest friend from our year seems to have literally vanished off the face of the planet. I’m coming to terms with the fact that this reunion will consist of making smalltalk with veritable strangers who are all doing impressive things such as running Black communications for the entire Republican Party (it’s a real job!). I’ll chat with classmates who have children, or advanced degrees, or high-paying corporate jobs, or property — things I have no interest in getting, the lack of which will still leave me feeling inadequate and increasingly sarcastic as I attempt to talk about my own accomplishments: a liberal arts degree in Anthropology and Cinema Studies, and a very large collection of vintage hats.

1. It’s so nice to see you! (My Xanax just kicked in.)
2. My hair is different, thank you for noticing. It was time for a change (…back to the way it grows out of my head).
3. I’m very seriously considering grad school. (Tisch’s MFA program had an open reception at the MoMA one night, and there was an exhibit I really wanted to not pay to see.)
4. I’m an employed writer. (I am employed. I am a writer. I am not employed as a writer. Minutiae.)
5. I dabble in Television Criticism. (Once upon a time I wrote down some thoughts about “Dr. Quinn: Medicine Woman” and posted them on the internet.)
6. I’m a freelance costume designer. (I have perfected the two-piece A-Line skirt.)
7. And when I have the time, I do some freelance personal styling, too. (I have, at times, suggested to a friend that his shirt is too loud for the occasion, and have often stood in silent judgment of people who wear jeans and sneakers to Broadway shows.)
8. I’m totally donating to the capital campaign this year! (I’ve just told you that I’m employed as a writer, so I will leave you to decide on the truth of this statement.)
9. Yeah, I’m living in East Harlem now. My rent is terrible. (My rent is amazing, but you look like a Finance Bro with a Groupon-purchased real estate license and a lot of friends moving out from the Bay Area to work at a DUMBO-based startup. As far as you are concerned, my rent is terrible.)
10. Living in New York is great. (Coffee and a piece of pumpkin bread costs $8.46 every morning, I got stop-and-frisked on the train once, this city is a literal hellscape, and yet I can’t convince myself to leave.)
11. My family is fine. (Remember that one awkward time I tried to explain to you that my brother was adopted from New Jersey and you replied, all shocked, “Wait, Black people adopt? From this country??” This is not a conversation I want to prolong.)
12. Nope, no boyfriend, I’m between relationships right now. (But thank you for thinking that I’m capable of having a stable relationship and not just hooking up with strangers at comic-cons. This gives me hope.)
13. I was so excited for this reunion! I signed up immediately! (My presence here is the result of: A) an excessively long email chain started back in December, in which I emailed the four friends I had in my graduating class of 90+ people and exchanged a long series of “well, I’ll go if you’ll go; there will probably be an open bar” messages until it was finally decided that we would actually attend; and B) The acute — potentially misplaced — sense of responsibility that I feel to show up to these alumni weekends so that all the current Black, Latino, and Asian students on campus will know that alumni who look like them do exist in this sea of whiteness.)
14. Actually, I haven’t kept in touch with my roommate. I have no idea what happened to her! (She suddenly left in the middle of the school year. Still working out the statute of limitations on that one.)
15. So sorry I missed you at the five-year reunion. I wasn’t there. (I was there, but two hours in I decided that the largest mall on the east coast would be less mentally overwhelming than this sea of Nantucket Red and Tory Burch flats, so I drove to Nyack, got some new piercings, and caught a 3pm showing of Bridesmaids.)
16. My God, you haven’t changed at ALL! (Which is terrifying, because I distinctly remember you being the kind of kid who peed in jars and poured it out of dorm windows onto the heads of unsuspecting freshman while rapping all the lyrics to DMX songs. All of them.)
17. Yes, I’ve seen most of your TV appearances. (I have not. I cannot afford cable — see above: “writer”.)
18. Yes, I’ve read Big Magic. Yes, I agree, it was totally life-changing. Yes, you should text me the details of your bi-weekly mommy book club, it’s so nice of you to invite me! (The only self-help book I’ve read, ever, is Shonda Rhimes’s Year of Yes, and the only reason I’m even engaging in this conversation right now is because Shonda told me to do the things I’d normally say no to.)
19. Really? That’s fascinating. (I will continue to engage in this conversation with you, because I want to see how many times you’ll stop to count to ten instead of actually taking the plastic sword your child is using to beat the back of your knees away from him. Current count: Eight.)
20. I’ll try and go to more alumni stuff in NYC, definitely. (The last alumni event I went to was hosted at some Ivy League school’s East Side club and they wouldn’t let my dad inside until he went to The Gap and bought a tie to go with his suit jacket, so I’m good on alumni events, really.)
21. Please! Speak freely. (Absolutely nothing you say to me will end up fueling a bitter five-glasses-of-wine-2am-pitch-letter about my personal boarding school angst to several major publications. No, really, speak freely.)
22. Just friend me on Faceboook, I don’t really tweet — who even has the time to keep up with all of that these days, am I right? (I talk less about sex and the men of the CW on Facebook. Also, it’s easier for me to ignore you there. )
23. I do kind of miss it here. (On the one hand, they used to shut off our internet at 10pm, my graduating class only had nine other Black people, the food was terrible, Latin was really impossibly hard, I did not date, and there were times when I felt closer to my online friends than I did to anyone within a mile radius of me. On the other hand, I often had an entire ice rink to myself for hours, I learned to love theatre, I had teachers who suggested that I take screenwriting instead of Algebra, I learned freedom at the age of 15. My feelings are complicated, but I do kind of miss it here.
24. Anyway, yes, I would love to signup for a combo Barre/Crossfit class with you. That sounds like a much better way to catch up after ten years than brunch. (I can’t wait to chat again in five years.)