91 Comments

You poignant reflection of the pain and joys of high school and a romance take me back to my own high school years. My hunch is it will do the same for many of your readers. Your descriptions and details are brilliant and illuminate your experience, allowing us the privilege of knowing you better and more completely. Exposing our vulnerabilities, instead of keeping them hidden, as we know now, is a strength although then it was a scary proposition. I married a high school sweetheart whom I met in the 5th grade, she in 6th and we lived two blocks apart so kind of grew up together, attached. That relationship came apart in college but we patched it back together married at an early age, 22 & 21, she a year older, had 3 children and divorced in 1995. That's another story for another time. Thanks, David, for another sterling post.

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David, did not send that number and perhaps this is not from you. Will send you message to be sure the scam or hacker is blocked or removed.

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It's a hacker/someone impersonating me.

I have alerted all the Substack people i know to remove it.

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Thanks Gary for your comment.

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I was in some ways fortunate to attend a small, rural school without enough kids to constitute proper cliques. I’d not have done well at the sort of school portrayed in movies.

I can’t understand the appeal of being “cool,” as it seems to be more about conforming than accomplishing anything. I couldn’t have fit well into any clique and am grateful I’ve never had to.

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This is such a sweet story that I felt viscerally. There is nothing more tender, exciting and engulfing than a mutual exploration of who we could be as adults, as children. The release of a certain kind of innocence, and a maturation of self. You captured that perfectly here.

And I’ve always loved the “you and me against the world” vibe of a John Hughes film.

I love this story and am looking forward to reading the next, and (hopefully) your love story with your wife, too. Redemption is on the horizon :)

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Thanks Cici. I wrote that story before this one. Here it is below. It's one for my favorites and was also very emotional for me to write.

https://robertsdavidn.substack.com/p/you-had-me-at-a-glance

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Lovely writing…I feel like I was there (just not in the cool clique). Did Heidi marry Cliff?

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Tell us - don't leave us hanging on that one!

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Yes, she did. What happened after, i don't know.

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Make something up - and make sure it's juicy!

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Jun 1Liked by david roberts

I loathed high school. I loathed school. It was a prison sentence as far as I was concerned. Only during my senior year when I learned to effectively flirt my way through...everything, was I able to exit Browning during class time and head to the Plaza Hotel's lobby where I'd read whatever the hell I wanted and watch adults check-in and out. I never once did my homework (do not tell my 5th grade daughter; about this I happily lie). I had an unrequited crush on a beautiful Hewitt girl (sister school; we were all boys at Browning). I was the captain of the tennis team. The head of the investment club (pretty much a Ponzi scheme, alas) and a truly shitty student with underachieving grades but good SAT scores. To this day, I can count four classmates as life friends. To quote Robert Frost "And that has made all the difference". The author, my eldest brother, was my hero. I thought he was super cool regardless of what he says or feels about that time, the 1980's. When one's path to diabetes was daiquiris (if you were tall and not a buffoon, you'd get served on second avenue at the age of 15) and Mrs. Field's cookies. I can also attest that Heidi was beautiful and her cookies bribes worked. My brother Samuel and I rooted for David's romantic self. It gave us hope. We too were solitary, bookish, nervous around girls. That David had Heidi was pure inspiration. My "Heidi" was a Benneton model the summer before college when I was 17. She was 19 and attended Mt. Holyoke. I had no business rolling with her. I suppose when it comes to young love, us Roberts boys over achieve. And, frankly, Heidi led the way.

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Thanks my brother!

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Jun 1·edited Jun 1Liked by david roberts

Sweet article. You often write about social hierarchies based on wealth, here is an example of a social hierarchy that has almost nothing to do with money.

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Jun 1Liked by david roberts

Debbie needn’t worry.

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Jun 1Liked by david roberts

So poignant and sweet. It reminds me of my high school days and the always present feeling that I didn’t belong. I chuckled at your description of the types of groups - we had the same ones. Floating between most of the groups I had friends in several but never fit into any really. Your post made me wonder about the boys I dated and how they really felt. Thank you for sharing. Looking forward to your next post!

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Thanks Susan.

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My first love in high school now reads my Substack. I haven’t seen him for at least twenty years. So…I often feel this awareness of how life moves in different ways as well as the joy of some kind of abstract continued connection from afar.

Thanks for the great story. A lot to think about there, David. And at that time, we’re just so ridiculously inexperienced and unaware. Maybe that’s part of what’s so wonderful about it.

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Thanks Kathleen. Does your high school love ever comment? I hope that soehow Heidi might see this as I want her to know how I felt and ideally would love to know how she saw it.

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Oh that would be lovely, wouldn’t it?

No, he doesn’t comment. But we have had some brief emails exchanges as a result. Much better than Facebook updates. :)

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Can’t resist ! A “Cliff” hangar.

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That's precisely the type of pun I adore.

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Jun 1Liked by david roberts

Enjoyable and painful. Wow, does anything in life compare to that first romantic experience? Somehow your very direct style emphasizes the subtlety of heartbreak. Thanks.

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Jun 1Liked by david roberts

Thanks for your transparency in your writing. I think we all knew a Steff like in Pretty on Pink. I had a Steff insult me in high school saying I looked uptight, a goody-goody and I would dump him anyway. It turned out later he did have a crush on me, but the words stung. Some of my writing my husband has been hurt by, I've taken one post down. It's never my intention to hurt him or anyone. I've been that awkward child who became a more popular, attractive teen, but the insults to my character and appearance hurt to this day. I have to admit if my husband wrote about an ex I would have mixed feelings. I also realize that his past relationships make him the person I love so much today.

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Thanks Jane. I just "travelled" to your Substack and subscribed. Your content is very intriguing to me.

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Thanks so much for subscribing and for complementing my writing. I've always enjoyed your post too

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Jun 1Liked by david roberts

What a beautiful and tender piece for many reasons, but most of all because all of us well know the seemingly never ending desire, pain, and embarrassment of the unfledged. And thank you for the postscript that answered a question I asked myself a hundred times as I read - is this writer's courage or alcohol induced craziness? What obliviousness has come over this man?! More seriously, a very wise friend once observed that the marriage process has a very strong element of violence to it - as it threatens, breaks apart, and redefines the bonds and inner workings of two families in order to create a third. In your case, it was the social castes that went through the process - though the observations you make and the lessons you learned/teach are at many levels universal and can be seen in circumstances large and small.

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Thanks Sam. I survived, but there were moments...

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Oh David, I love this essay. I was right there with you. Your writing is so beautiful and this story is very moving. Looking forward to Part 2 and to talking again soon!

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Thanks Debby.

Let me know as I'm back and around.

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I’m ever intrigued by the nuances of others’ relationships so your honest inclusion of Debbie’s feelings and your daughter’s explanation is most interesting to me. I assume most healthy couples don’t mind hearing about prior loves, as those experiences built the people we come to love. But maybe it’s those tales of past loves that feel unfinished or cut short, the ones that are told as if the past love had this innate power to elevate…to transform….i think we all want to feel “chosen” and yet there are some stories of people’s pasts that are told in such a way to make us doubt that we were actually the first of those choices. This happens not just in romance but in work life, social life, family life. Anyway, really appreciate you sharing that personal family nugget at the end AND appreciate Debbie permitting you to leave that nugget it - cuz it’s a vulnerability for her to have her hurt shared. Y’all are a solid couple.

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Thanks so much Trilety. Writing about a past love carries with it risk and, as you point out, when it's unfinished business, it can sting.

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Very timely. When I was editing a certain story about my past, I started to write "almost all my boyfriends were Jewish" but when I mentioned this to my husband (of 61 years minus a week!), he said something like "Wait a minute, how many were there?". You don't talk about these things when you are first dating and then not much at all and life goes on and the issue doesn't come up, so even after all these years and an incredibly close and strong marriage, the sheer idea that there were other people beforehand somehow stings much more than it should. Your Debbie is in good company.

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Thanks Ann. I think a spouse may want full credit as the initial discoverer. That's what Debbie told me.

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Could be. I don't dare ask. Ray (husband) is super-intellectual and capable of discussing nuance until the cows come home, but underneath there lurks a certain caveman mentality!

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