This is going to be very hard to write now, and after what was said last night you probably don’t even want me to write anything.

So began a painstakingly composed yearbook inscription written about half a century ago by a graduating high school senior to the boy she was saying good-bye to. It was for his eyes only. But today, to the astonishment of that author, it’s posted online at the website classmates.com, where any of us may pay to violate her privacy by reading it.

Classmates has decided to traffic in nostalgia, but it traffics carelessly. Nostalgia is as friendly and caressing an emotion as we know, which is why it’s eagerly shared and easily turned into money. But nestled among the golden oldies of our collective memories is the jagged residue of love, longing, and loss. These are the complicated and eternally painful memories that are no one’s business but our own.

Last November Mark Goldston, CEO of the parent United Online Inc., explained to investors that Classmates, launched in 1995 as a way for former schoolmates to get back in touch, was being refocused to become “the leading provider of nostalgic content on the Internet.” At the heart of this strategy is its yearbook project. Classmates is scanning old yearbooks and posting them online for paying members. “We’ve more than doubled the number of high school yearbooks available on Classmates in the past quarter alone,” Mark Goldston told the investors, “so that we now have more than 45,000 versus just 20,000 last quarter.”

There will be other “cool stuff” as well, he said—such as old issues of the Saturday Evening Post and Sport magazine to browse through. “We have kind of held back from doing any real aggressive member marketing,” Goldston explained. “We’ve done some, but as I said, we’re still remodeling the hotel, and you don’t want to bombard your members with the same message too many times. You kind of have to keep that message powder dry so when you’re really ready to roll it out it has maximum impact. So while we are certainly teasing the people and sending them out certain information, you really haven’t seen the big nostalgia carpet bombing that we intend to do. And I say that in a positive vein to our member base because this yearbook product is really compelling.”

Classmates is a sort of B-list social media site in need of something compelling. Classmates and its much smaller sister sites overseas claim some 60 million members, but not even a tenth are paying “Gold” members, and Goldston conceded to the investors that he’d been offering them too little of the “number one stimulant on the Classmates site . . . graphic content.” When Classmates made news last August, it wasn’t flattering. Andrew Cuomo, then attorney general of New York, announced Classmates was one of a handful of sites that would each pay $2.1 million in fines and restitution over fraudulent hidden fees.

But of what consequence is this petty discord against the satisfactions Classmates now proffers? A high school yearbook stirs the soul. I came across a series of yearbooks on Classmates that once belonged to a boy I’ll call Jim, and as we leaf through each in order we watch a boy become nearly a man. The inscriptions alone tell a story. When he was finishing eighth grade, decades ago, a buddy wrote in Jim’s yearbook, “To a real, real, real neat kid,” and a girl wrote precociously, “You have a darling smile and a conquering personality.” A year later, at the end of Jim’s freshman year, another girl wrote, “To a real cute guy who is lots of fun. Good luck always,”

How Classmates got hold of these books isn’t clear. Jim’s sister tells me the books wound up in their mom’s basement, and when she moved to assisted living four years ago and the house was sold, an auctioneer sold off the contents nobody wanted. Jim didn’t want his high school and college yearbooks, and they sold for $30.

“They could have passed through 15 sets of hands since 2006,” the auctioneer told me. Some of the yearbooks Classmates scans are provided by members, but the “vast majority,” says a company spokesman, are purchased from yearbook collectors.

By Jim’s sophomore year, the boys and girls seem to be looking at each other with widened eyes. The longest inscription in this yearbook is from a girl who wrote, in part, “Boy, we have sure had gobs & gobs of laughs & I really hope we will sit next to each other in some class! Your really great & I really like you a lot a real lot! And I mean this sincerely! Love ‘n luck!”

It turns out that their junior year they dated—though as that book hasn’t been posted, Classmates offers no public evidence of this fleeting romance. By the time Jim’s senior yearbook is issued his life has taken a turn. Someone I’ll call Pam makes her first appearance in his yearbooks, and her anguished inscription fills a page. It also invites a question Classmates’ yearbook project doesn’t seem to have thought much about—whose business is this?

This is going to be very hard to write now, and after what was said last night you probably don’t even want me to write anything. Jim, I’m sorry—sorry that I’m not the girl you need, sorry that I didn’t meet you two years ago, sorry for the thing I’m doing and the things I’ve done to hurt you. In a way I almost wish you could hate me—it would make everything much easier. Maybe now you do.

Jim, even though you, in future years, will maybe try to forget me or dislike me, I’ll always remember you and all the fun we’ve had together. A senior year is always filled with so many memories (mine is certainly no exception) and you are such an integral part of my senior year that I could never forget you. I’ll remember our first date—the football game in the rain, the “pffft” at your aunt and uncle’s, telling ghost stories in Susie’s driveway, trying to get you to yell at the basketball games, dancing in bare feet at all the dances with you, and the boy sitting along the aisle watching the senior play. No, I could never forget—and I’ll always admire and respect that boy—he’s one of the most wonderful persons I have ever known.

I’m going to miss you next year, Jim, and I do hope we will write to each other. I’m sure you’ll spend a successful year at college, and that every year of your life will be just as successful. You deserve only the finest girl in the world—and only that girl is worthy of your love. I hope you find her Jim, and that she won’t be bitter toward me for sharing some of it.

God willing, may all your dreams come true—and may you find happiness soon. I wish I could give you that happiness, Jim, sincerely I do.

Always,

It’s a Dear John letter, written by one high school sweetheart to another as their lives diverge. And if that had been that, perhaps they both could read Pam’s inscription today and smile, and perhaps neither would care who reads it too. But that wasn’t that. Their old classmates—and, seriously, who would ever peruse these ancient books but old classmates?—will read this knowing they wound up married anyway, and they had children together, then separated, and then divorced.

Jim’s present wife told me he had no interest in rehashing the past, but Pam wanted to talk about it. She couldn’t remember what she’d written in Jim’s yearbook but she was pretty sure it didn’t amount to much, and then I sent her the text—with a note that reading it had troubled me. “Whoa!” she replied. “I am also unexpectedly affected . . . perhaps ‘troubled’ isn’t the right word for the impact it has on me, but you are right that it brings back feelings, memories, emotional history that suddenly feel like yesterday.”

Pam e-mailed Jim’s wife a heads-up about the yearbook, telling her “none of that history belongs on line without our knowledge and permission.” And she told me she wonders how other people will react as Classmates disinters words they once wrote that “might be more painful, more embarrassing, even more private than mine.”

Not that she felt embarrassment. “Actually,” Pam reflected, “I am quite moved by the tenderness, articulateness of this 16-year-old girl who seems to have made a decision to move on without this boy in her life—and that is where she was when she wrote that inscription; the irony of course is that 4 years later they walked down the aisle and shared 19 years.”

On its website, Classmates has posted a 5,200-word privacy policy that asserts its commitment “to protecting the privacy of our members’ personal information.” But this is privacy as we think of it in the age of social media, the sort of privacy that marketers and identity thieves might like to breach—the privacy of data. It bears no resemblance to the privacy once counted on by teenagers trying to explain overwhelming feelings to each other.

Classmates tells me it’s aware there could be problems. “When someone notifies us that they are not comfortable with having a yearbook up on our site that contains notes that either they wrote to someone else or that someone else wrote to them, we immediately take the yearbook off the site,” said the company spokesman. “If we can digitally remove notes/comments in question without affecting the integrity of the book, we do so, and repost the book to our site. If we cannot remove the notes/comments while maintaining the integrity of the book, we remove the book from the site permanently.”

In other words, we put it up and if someone complains we take it down.

“I don’t know how they can say they have a privacy policy unless they contact every single person who’s written in those yearbooks,” says Pam. But to tell the truth, she’s less put out than she could be. She tells me, “I have been thinking about things this week that I haven’t thought about for years. I’ve shared this with my daughter. She has all kinds of questions. She said, ‘Boy, I can’t believe you wrote that when you were 16 years old. What happened? It sounds like you were breaking up and you married him?’ It was a powerful mother-daughter talk.”

Pam’s feeling more reflective than violated. But still . . .