Illustration by Brian Taylor.

A few years ago, my friend Kabir raked in an amazing Christmas haul at work. “I got a cashmere sweater, really expensive wine, a super nice pen, a Le Creuset pan, a free dinner at Craft, opera tickets to the Met and a $150 watch,” he remembered. “Plus gift cards to everything from Dean & DeLuca to Banana Republic. I never got cash, but the gift cards added up to over a thousand bucks!”

Kabir is not a hedge fund manager, a high-end male escort, or—despite the fitting first letter of his name—a backup Kardashian. In fact, at the time of this unbelievable bounty, he was a 25-year-old assistant kindergarten teacher at the Grace Church School. 

When the holidays roll around, there are plenty of handy guides to tell you how much to give your mail carrier, your doorman or your dog walker. But what to get the beleaguered liberal arts grad marinating in Yellow Tail Shiraz and student loans who molds the mind of your child?

I’m referring, of course, to teachers, the most vexing of all gift recipients. They provide a service, sure, but educating your flesh and blood isn’t exactly on par with touching up your roots. Then again, you’re probably a lot closer to your stylist than to the person you entrust with your children every day. Their gift shouldn’t be a nominal tip, but it’s impossible (even bordering on inappropriate) to make it personal. And, perhaps most important of all, it should send the right message, whether you intend it as a token of appreciation, a status symbol, or even a cleverly disguised bribe.

I find myself already agonizing over a future of gift-giving. As a freelance writer, I may never make much more than a teacher’s salary, so will they understand if I eschew Bergdorf Goodman in favor of a pan of gingerbread? (What if it has Guinness stout in it, does that sweeten the deal?) Will the value of an iTunes gift card mean the difference between a fun, gossipy parent-teacher conference and one in which the teacher gives me the side-eye and pointedly calls me “ma’am”?

Teachers themselves attest that their haul this time of year ranges from a tower of home-made snickerdoodles to a necklace hand-picked from David Yurman’s private collection. “Gift certificates are probably the best,” one told me, “Because cash can be awkward.” But off the record, the consensus is that the higher the price tag, the better the gift—after all, there’s always resale value on eBay.

The city’s public schools are bastions of construction-paper cards, and well, worse. Susie, a teacher in Jackson Heights, gets “lots of Russell Stover chocolates, regifted jewelry and the like,” she said, adding that arroz con leche is a real treat in comparison. One wonders whatever prompted her to relocate to Queens from the Upper West Side, where a former private school colleague of hers was given $600 in cash one year. (“Any sort of thank-you means a lot,” she insisted.)

The thing is, public schools have tried to ban gifts outright. (I hear that Mayor Bloomberg also sends a yearly memo asking teachers not to accept presents of monetary value, which is summarily ignored.)

So what usually happens now is that a volunteer will collect money from everyone for a class gift, through a series of emails that some parents disregard altogether.“I don’t know what everyone’s situation is,” said a class parent in charge of just such duties. “But there are always people who give nothing and people who give a lot more than average, and am I going to think the people who ignore my emails are assholes? Yeah.”

Private schools have cheapskates too. One class parent recalls a “crazy rich” father who took issue with the $30 minimum donation she requested from each parent toward the teacher’s holiday gift. “You’re spending $30,000 a year to send your kid to school and you’re richer than God,” she said. “And you’re taking issue with spending $30 on your teachers?”

That’s chump change to Kelly, whose kids attend a private school where parents typically pony up $250 for teacher gifts. “Some give one really showy thing, like a bottle of nice Barolo, and others make a gift basket with a lot of smaller things that give the impression of being more extravagant,” she said.

This, naturally, incites panic. “You don’t want to be the only one giving a bag full of Clinique samples or whatever when everyone else is going big,” she said. “So right now, in early December, you get a lot more chatting during drop-off, with people finding out what everyone else is doing. You wonder, is this enough? Am I getting them less than everyone else?”

A few years ago, it was much worse. “All I remember is that one year I was buying little boxes of Godiva truffles, and the next year I was seriously considering getting my youngest daughter’s third grade teacher a Chanel wallet,” said Joyce, a mother of three daughters who attended an elite all-girls private school.

One teacher, who has been at her school for nine years and who refused to allow even her extremely common first name into print for fear of being fired, says that she once received a class gift (funded collectively by over 25 parents) with a retail value of almost $7,000.

To curb competition, some schools have started collecting money anonymously to divide equally among teachers, not unlike tips at a dive bar (although presumably more lucrative). Meanwhile, Brooklyn Friends, Brearley and Collegiate, among others, have a homemade gifts-only policy to avoid any haggling over money, but the results have been mixed. While some parents “buy cookies from a bakery and just stick them in a Tupperware,” according to one former teacher, other school parents interpret “homemade” to mean much more than cupcakes.

“A well-known photographer once offered to take my head shots,” said the former teacher. “And I rationalized it, because it was technically something he made. It was just something that should have cost me tens of thousands of dollars.” (Incidentally, a note to my son’s future educators: I would be happy to write a column about you for no charge.)

But the unrestricted, above-board free-for-all continues at plenty of places. And I don’t think I’m telling tales out of school to say that in the end, that is the policy that some teachers love best, if not parents. “The guilt that very rich parents feel at having their children educated and raised by young people making $29,000 a year is a strange thing,” Kabir—now out of the educational sector and resigned to his gift card-less existence—observes. “But, being young and broke, it was fucking awesome.”

Will Ferrell did not have a child graduating from the school. And he is not among the school’s notable alumni, which include broadcaster Barbara Walters, filmmaker Sofia Coppola and New Yorker film critic David Denby. The actor’s presence, as a few resourceful parents learned and his publicist confirmed, was a personal favor to Today host Meredith Vieira, who had a daughter graduating that day.

“You might wonder why I’m doing this,” Mr. Ferrell, dressed in a nondescript gray suit, told the assembly from a podium in the school’s quad. “Well, I was paid $10 million—so this will be the last graduating class!”

Unfortunately, the comedian’s jokes failed to impress an audience that included at least one descendant of gourmet supermarket chain founder Eli Zabar, also an alumnus, and a li’l Lehman Brother. 

Mr. Ferrell called Dr. John Love, the principal of Upper School, the “Love Doctor.” He informed the audience that by the time he graduated high school, the “Corrupt Non-Culture University School,” he had kissed one girl, one time. He suggested that perhaps a member of the graduating class could go on to be the first black president, except that that had already been done.

“He totally missed the punch line!” said Victoria Goldman, author of the perennially popular Manhattan Family Guide to Private Schools, there to support her graduating nephew. “He should have said that someone here will be the first Jewish president! He just fell flat.”

Mr. Ferrell concluded: “Seniors, repeat after me: Dare to dream, dream to dare … love the Kardashians!” And the audience finally surrendered and shook with laughter.

But what is the actual reality?

This year, graduation week began with St. Ann’s, the moneyed-bohemian, touchy-feely, grade-less crown jewel of Brooklyn Heights. Once dominated by the children of artists and writers—alums include designer Zac Posen, gallerist Vito Schnabel (son of Julian), actress Eva Amurri (daughter of Susan Sarandon) and spawn of Sigourney Weaver and Ellen Barkin—the school has in recent years welcomed the children (and money) of investment bankers looking for a little artistic street cred.

Around 7 p.m. on Tuesday, June 9, parents, many in cocktail frocks, filed into St. Ann’s Church on the corner of Montague and Clinton Streets. Their kids wore suits and colorful knee-length dresses instead of caps and gowns. Mini-fans were distributed at the entrance; the old church often gets stuffy.

The St. Ann’s graduating class elects five student speakers, the most memorable of which was a smiley young girl in a floor-length, sleeveless cream gown and weighty diamond earrings named Kimi Lee.

Ms. Lee, whose father teaches print-making at the school, struggled to describe her unique education at St. Ann’s. Maybe it was like a carnival, or maybe …

“It can be an orgy, because, after all, the St. Ann’s ethos has always been uninhibited, experimental, gratifying and incestuous,” she told the audience, before offering that perhaps the best adjective to describe her education was “delicious!”

Another speaker, Sam Sullivan, a student of poetry, said some very romantic things about “enchanted gardens” and “childish frolic” and the importance of “fantasy!”

“Before anyone in the so-called real world has a chance to fool us, the gardeners, the graduates, into believing that our lives are about power or money or anything else equally mind-numbing,” he warned, “let us go out and just be, because only good can come from that. In the real real world, there is nothing, but love.”

Mr. Sullivan then pulled out a guitar and led those gathered in a swaying, earnest rendition of ABBA’s Dancing Queen. 

Later that evening, the students would be headed to a rented after-party in a loft—the secret address was texted to graduates around 11 p.m.—where they would celebrate their commencement with ironic beer like Miller High Life and Busch; sweaty grinding; and privately hired security guards. The after-after-party was at Dumbo Park, where the graduates traditionally watch the sunrise.

At 10 a.m. the next morning, there was a power trifecta of graduations.

At the West End Collegiate Church, mothers with carefully hair-sprayed up-dos and tweed designer suits swooned over their sweet boys with neatly combed hair and gentlemanly loafers, a surprising number of which spoke with British accents. In the audience, The Observer spotted the actor Hugh Grant, wearing a brown blazer and slacks, smirking as the Collegiate boys made their way inside. (Among the graduating class was a James Murray Fitzgerald Grant—presumably a relation.)

Before the director of the Museum of Modern Art, Dr. Glenn Lowry—whose son Nicholas graduated in 2000—delivered the commencement address, a tall, skinny, student-elected speaker named James Englander Underberg got up and referenced some raucous party behavior.

“In second grade, we learned the proper way to show respect for someone’s home,” he said. “For example, how to christen a host’s elevator by breaking a bottle and running away or help bleach a guest’s rug.”

Outside after the ceremony, some of the boys lit stogies. “I was born to hold a cigar!” a young man with freckles named David Rattner was overheard to brag. This summer, Mr. Rattner, who lives on the Upper West Side and is headed to Brown in the fall, will work for Mr. Bloomberg’s reelection campaign. “I have some plans for the future, but I’m allowing myself some freedom,” he said, adding that he has watched Gossip Girl, but found it a bit hollow. “It is a hyperbolic representation of my life,” he said.

“I wasn’t invited here today because I have some gifted capacity to deliver a message of inspiration for the future, no,” declared Ms. Washington, her hair pulled tightly back, dressed in a blue-and-white skirt suit. “You’ve invited me here because I am one of you—a Spence girl, through and through.”

Ms. Washington continued: “Your love and support for one another has gotten you worried a little about leaving here. You love Spence. And you are not sure what to expect. To that I will say, ‘Good, you should be a little nervous, because ladies, the world is not exactly like Spence.’” (Here the parents began to chuckle.)

“Make Ms. Spence proud!” later enjoined Bodie Brizendine, head of school.

Up at the Riverdale campus of Horace Mann, whose class of nearly 200 was four times most of the others, the red, gold, and white Chanel purses were in full bloom.

Upper East Side parent Debra Jaliman, “a Fifth Avenue dermatologist,” said her daughter was headed to the University of Pennsylvania. “It was her first choice; she got in early decision,” Dr. Jaliman bragged. “She worked so hard at Horace Mann and her dreams came true! It’s hard to get A’s here, so if you get the A’s, you’re going to get into an Ivy League school.”

A gentleman in a navy power suit and loafers was not so forthcoming, though he did allow that his second child was graduating from the school. “Horace Mann has been in the public eye a lot lately in a negative light,” he apologized.

Indeed, given New York parents’ traditional guardedness, it’s surprising that NYC Prep materialized at all.

But then again, it is co-produced by the formidable Liz Alderman, who attended the Brearley school for girls (considered the best in its class; as the saying goes: “Chapin girls sleep with the doctors, Spence girls marry the doctors, and Brearley girls become the doctors”) and then returned to teach at the school after Harvard. Another producer, Matt O’Brian, attended Stuyvesant.

“We’re just native New Yorkers that wanted to bring a fresh, East Coast perspective to the teen docu-soap genre and show the rest of America how New York kids operate,” Ms. Alderman said. “These kids have more opportunity than almost any other place on the planet.”

Ms. Goldman, the guidebook writer, expressed skepticism about the show. “Nightingale is the top school in the group!” she said disdainfully. “Anyone going to the top 10 or 15 schools would be smart enough not to be a part of this.”

Ms. Alderman was responsible for easing the concerns of interested parents, who would have to sign off on their children’s participation. Most of them asked her, “If this were your child, would you let them do it?”

“My answer was always, ‘Yes, of course.’ Reality TV is now a fundamental part our collective culture and the TV landscape,” said Ms. Alderman. “It’s a genre that is not going to go away. … Take the reins and make this genre your own.”

The schools that participated did not allow filming inside their walls, and their names are not mentioned. But according to a few speculative online parents’ forums, the brash Peter “PC” Peterson has already graduated from Dwight, where another cast member, Jessie Leavitt, 17, is a senior; the pretty Kelli Tomashoff, 17, is a junior at Birch Wathen Lenox; Sebastian Oppenheim, the 16-year-old “player,” is a sophomore at the Ross School in East Hampton; Taylor DiGiovanni, 15, is a student at Stuyvesant; and Camille Hughes, 16, is a junior at the Nightingale-Bamford School. (Nightingale recently sent out a letter to parents and alumnae, clarifying that the school did not O.K. Ms. Hughes’ participation and advised against it.)

“Maybe the parents are thinking that this is a good opportunity,” Ms. Goldman said. “But … the focus should have been on college admission, not who’s hooking up with whom.”

Ms. Goldman then confessed that she’s writing her own (fictional) series about the world of private schools. Title: Admissions Impossible. She said MTV and the CW are both interested.

—Additional reporting by Caitlin Keating and Eliza Shapiro

ialeksander@observer.com