I Just Lived Every Woman's Fantasy

03/26/2015 05:39 pm ET | Updated May 26, 2015

Three decades after high school, I woke up to a Facebook message from the guy I spent my entire sophomore year pining over. To summarize, it said, "You were hot. I was an idiot. I missed my chance and late at night when I drink too much, I still think of you."

Oh. My. God.

How would my life have changed if he had only mentioned this 30 years ago? What if, instead of spending my formative years as an outsider looking in, I had been one of the popular girls with a cool senior boyfriend? His rejection has been a fundamental part of my story.

Everyone in high school feels like a fish out of water. While I wasn't as extreme as Sandy in Grease, I was a theatrical Jewish girl from Vermont at a New England boarding school where blonde hair, blue eyes and a talent for lacrosse were strong indicators of "It girl" status. X was a bespectacled, charming old line WASP, named for a college that was chartered by his ancestors. He attended an exclusive all-boy's elementary school on Park Avenue where he was groomed to wrestle, debate and wear a blazer and tie from age of 6. He was the first guy I met who wore pink Brooks Brothers boxers (which I only knew because they poked out the top of his khakis).

We kissed one night on a New York City rooftop over Thanksgiving vacation, and I spent the rest of my high school career plotting how to get him to like me. Thanks to my best friend Beth's encouragement, I delivered a well-rehearsed script outside the chapel a few days before winter vacation. "X, I would be delighted if you would escort me to the Gold and Silver Ball." (The Gold and Silver was a $100 a ticket charity ball that was straight out of Whit Stillman's Metropolitan.) When X agreed, I was so giddy, I told my English teacher the next day that I simply had to miss class so Beth and I could buy gloves for the ball. He was so stunned, he let us swap A Midsummer Night's Dream for a mid-afternoon shopping spree.

Now as an adult, it takes me two minutes to get ready for any event, but I can still remember how much time and care I put into getting ready for the Gold and Silver. In my grandparents' cluttered, overheated apartment on 77th and Lex, I zipped up my strapless black dress with a velvet bodice and puffy taffeta skirt and felt as elegant as Jackie Kennedy. As I pulled on my high black gloves, I imagined I was Audrey Hepburn at Breakfast at Tiffany's. And as my grandfather clasped the first of what would become a career defining style of rhinestone bling, I felt like Elizabeth Taylor in Father of the Bride. Then X called and cancelled.

My sister, who was a sophisticated high school senior at Andover at the time, whisked me off to Trader Vic's beneath the Plaza Hotel to cheer up with her friends. As I drowned my sorrow in Mai Tais, (to this day, I can't understand why they served us, as we were 15 and 17), my sister encouraged me to at least show up at the end of the party so I could claim my gift bag. As the party was practically over and I heard the gift bag contained my favorite Laura Ashley perfume, I thought it would be safe to go. As I rode up the escalator at the Grand Hyatt Hotel, X's best friend passed me riding down. "X is real sorry he couldn't make it tonight."

Despite X's devastating rejection, I still called him when I was in New York over Thanksgiving both my junior and senior year. Thankfully, it was before the days before caller ID, so he had no idea how many times I hung up before summoning the nerve to say hello. And both times, he blew me off.

The summer after high school, I was finally popular. Absolutely nothing changed, not my weight, style nor talent for sports. I simply went from being the token to being a counselor at a Jewish sleepaway camp. To fellow counselors named David Weinstein, Lewis Felderman and even Alistair Lipshitz, I was the belle of the ball.

I was drawn to see X one more time before I left for college. I called him and surprisingly, he invited me to his spacious Park Avenue apartment. He led me past sailing photos from Nantucket and portraits of somber-looking relatives and took me to his bedroom, the epicenter of every high school fantasy. X was charming and talked with me about all the fun I had to look forward to my freshman year at Brown, and then, he leaned in to kiss me. Surprising myself even more than him, I pulled away. "Sorry, X" I said. "You missed your chance."

Ironically, my son now attends X's alma mater. My little boy is being groomed to be as smart and sporty and preppy and charming as X. Every day at pick up, I pass X's plaque on the wall and though I have certainly moved on, there is still that prick of pain reminding me of the time I was stood up at the Gold and Silver so many decades ago.

When I woke up to X's message, there was that well-earned feeling of 'HA!' But instead of rejecting him as he did so long ago to me, I wrote him back and just asked, "Why?"

It is with his permission that I paste our correspondence below. I read it to my son so that when he becomes that preppy teenage heartthrob, he will tread carefully. When he likes a girl, I hope he will have the confidence to let her know.

I have realized that closure is even sweeter than revenge. X is married and lives on the other coast of America. I travel from Manhattan every other week for my new career as a Vermont family innkeeper at the Wilburton Inn. There is no way we are riding off into the sunset together. And though he would totally not get this reference (which only illustrates why our love was never meant to be in the first place), our encounter brings to mind one of my favorite lyrics from Fiddler on the Roof:
"It doesn't change a thing, but even so. After 25 years, it's nice to know."

X: I don't know that it will ever be appropriate to say this, but... thank you for at least being marginally interested in me in high school. I was (and still am) a dweeb, but you were (and still are) some kind of hot, and the fact that you may have had a glimmering of interest in me was huuuuuuuge for me. Thank you for your terrible decision-making!!!

I hope to catch up with you some time now that I'm slightly less awkward, although, alas, more unavailable. I've always enjoyed hanging out with you, reading your posts and just generally being associated with things that you're a part of. Yes, it's St. Patty's Day and yes, I'm quite drunk, but no matter... the truth is that you were a big deal to me and I blew it... and to this day, I remember how much I liked you, and I still wish you nothing but the best

I guess what I'm saying drunkenly is that I will always like you, if only as a friend now. And again, thank you for being you.

ME: Wow! What a surprise to wake up to your message and what a lovely thing to write, no matter how tipsy you may have been when you hit send.

Of course I had a HUGE crush on you. Beth and I spent the better part of sophomore year trying to get you to ask me out. I recall that we fooled around once on a NYC rooftop and I called you for the next two Thanksgivings hoping we might rekindle the flames.

So the big question is, why did you blow me off? It's 30 years and a lifetime ago, but it would mean a lot to me to understand.

In my new life full of firsts and colorful adventures, you certainly made my day. Thanks for saying hi.

X: Ha... Well less drunk now, but still happy to hear from you.

The truth is I can't remember (as disappointing as that might be for purposes of closure). I probably was just an idiot the first time. I'm guessing that at least for the second Thanksgiving it was because I was dating the girl who later became my wife (so that's a decent reason).

I'm not sure what prompted me to write last night... beyond the general mistiness that comes on from being deep in my cups. But I look over the message I sent, and it looks pretty accurate to me. You made school more fun, and I'm glad we were there together. And I certainly remember the rooftop with fondness, although with some embarrassment.

Just for clarification -- the embarrassment of the rooftop comes from my recollection of my horribly inept "moves." I couldn't have been happier to be on the rooftop.

ME: Hmm. I think you owe me an apology for blowing me off at the gold and silver circa 1985. Beth and I actually told our teacher that we had to miss English class so we could go to Boston and buy black gloves at Bonwit Teller for the ball, and he was so stunned, he agreed.

And no matter how many diamonds or accolades from the press, I will never forget riding up the escalator as your friend rode down the other way and he sneered "X's real sorry he couldn't go with you tonight."

X: Wow!!! Then I was a fucking dick! Sorry!! You were super hot, and I was an idiot! Please accept this as a formal apology. That was inexcusable.

ME: I don't know... I think your only way out of such bad manners -- especially for a boy who has been bred to know better -- is for you to really mull over why you ran away. A bird in the hand, my friend...

X: Fair enough. But at 30 years removed I make no promises. But I am sorry for hurting you.

ME: Getting closer...

X: Mulling may take some time... because I'm surprisingly good at suppressing memories. And even better at forgetting whatever unflattering emotional truths must've prompted them.

ME: I've already waited a decade longer than Penelope.

X: I don't think I can use "I was fighting Trojans" as an excuse.

It probably comes from something like "fear of actually being with a real live girl" or "misplaced vanity that made me think I should play the field like a playa" or "who the hell knows what goes in 17-year-old boys minds, they're all dicks."

But it's also possible that I was captured by a sorceress who turned my crew into animals. And sorting that kind of thing out takes its toll on relationships.

So I'm not precisely sure of the reason. But it's almost certainly something that is ugly and stupid inside of me... because it certainly led to behavior that was both ugly and stupid.

Thank you for calling me on it. I wish I had better answers.

ME: Hmm... I have a Broadway opening tomorrow and need my beauty sleep but I have faith that with another Irish celebration you will have a great revelation if your first email was true.

X: Again... sorry.

ME: Next time you come to New York, you can make it up to me. I may still have the gloves.

X: Deal.