Jill, The Dot Connector

(Editor’s note: Welcome to Living Eulogies. All recollections are accurate in the author’s mind only. Apologies in advance to everyone who has different recollection of the same events. Send all complaints to your Gwenyth Paltrow’s laywer. Void where prohibited by law.)

With the benefit of numerous trips around the sun, I’ve learned that whatever it is that you’d like to call that higher power that has set up this vast and wonderous universe and plopped us human beings on some random ball floating out there decides every once in awhile to a put a person in our lives who is kind of like the setup man in baseball.

You know the setup man in baseball, right? He’s the guy who comes in after the starting pitcher is done and before the closer comes in to finish out a tight game. The setup man often gets the more difficult outs, while the closer gets most or all of the glory.

In this thing called life, I’ve had a few people whom I thought were closers, whom I thought were part of my endgame, if you will, but who, in retrospect, were people who helped me transition from one phase of life to another and without whom, I never would have been in the right place or right mind frame for the massive events and changes that followed.

The most recent of these people was a person at work whom I started to get to know better in the fall of 2018. I thought this person was going to be my ride-or-die best friend for the rest of me life. We connected in an odd and wonderful way that led to a lot of confusion and created a ton of damage, but at the time, there wasn’t a thought in my mind that this person was playing a huge role in preparing me for the amazing things that have come in the wake of the explosion of that relationship.

Without that person, I never would have faced the most challenging of my inner demons. I would have gladly bounced along, descending slowly, ever so slowly, into ruin. I see that now, but, of course, back then, I thought I was doing OK. The worst of the inner demons can be almost imperceptible as their tiny whispers keep you complacent and on the path to destruction.

So now, even though that relationship is over, I can find ways to be thankful and to look back fondly on that time and be appreciative for that person who was a much-needed dot connector to get me from where I was to where I needed to go as I continue to trace the outline of this beautiful picture created by the puzzle known as life.

Before that person — well before that person — there was Jill.

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I met Jill in the summer between freshman and sophomore years in high school. That I met her at all is a thing that beat almost impossible odds. Jill was born and raised in the tiny town of Harvey, Iowa, population 238 (as of 2021), while I grew up a thousand miles away in Suburbia, New York. Were it not for our parents’ decision to vacation on the same week of the same month of the same year on some obscure dude ranch in the middle-of-nowhere Texas, I would never have known a girl named Jill Westburg existed, and I wouldn’t have met my wife.

And the truth is, we almost weren’t able to go on that vacation. My great grandmother — a spitfire of an old woman by the time I got to know her, a recovered Flapper from the 1920s who was a pretty shitty mother but who taught me how to play dominoes and rummy and shuffle cards the right way — broke her hip the week before we were to leave. My parents were very much in favor of canceling the vacation, as we were the closest relatives.

But when Grandma insisted we go, well, no one really ever went against what Grandma wanted because she was a tough old bird. So we went.

I was about to turn 15, I believe, when this vacation happened. While I was there, the relationship I’d been in with a great girl exploded because I’m an idiot, and I was dumped on a long-distance call on a pay phone in the lobby of the ranch. Ouch.

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In my experiences as a youngster on vacation, no matter where we went, I’d fall in with some crowd of like-minded kids and spend the time not spent with my family with these folks. This afforded me the opportunity over the years to get to know some really interesting people from around the country — and the globe.

I don’t remember exactly how I started talking with Jill and her family, but I imagine it was while we were on the backs of our horses for the week. Jill was there with her parents, sister and some cousins. I was there with my parents and sister. Over the course of the week, I got to know Jill casually, and she got to hear all about my breakup and broken heart.

And then we went our separate ways.

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I thought that was the end of this interesting girl from Iowa’s role in my life. That was until I came home from school one day and there was a letter in the mail addressed to me with a Harvey, Iowa, return address.

Jill had called or written to the ranch asking about the kid from New York who was there the same week she was. In an era before data privacy — especially of minors — was a thing, they gladly handed out my address to her, and she wrote.

It was a friendly note, with a “Remember me?” theme. And I did. It wasn’t that Jill was all that memorable, but she was from a walk of life totally different from mine, living on a farm and having farm chores and being in 4H and stuff like that. That existence couldn’t have been further from mine in Suburbia. And so yes, I certainly did remember her.

Jill was an awkward early teenager back then, with braces, frizzy hair and all the insecurities of a girl that age. That matched well with awkward high school me. So we started writing letters back and forth.

I was thinking about that this morning on the drive to work, how we’d pour the goings-on in our lives into those letters, put a stamp on them, and then wait patiently for a response. Those times were simple and fun. I think kids who have instant communication with people across the globe are missing out on the fun of pen pals and the thrill of a letter arriving in the mailbox with the familiar handwriting of a long-distance friend.

Our letters were infrequent at first, filled with the goings-on of teenage lives that were very different based mostly on geography. It was fun having a far-flung friend who had experiences I could never have dreamt of having, growing up where I did. Slowly but surely, we got to know each other …

… and realized we kinda liked each other. As in liked liked each other.

I’m not sure exactly who felt it or said it first, but our letters took on some elements of flirtation. We exchanged school photos when they were taken and came out. It wasn’t that I thought Jill was beautiful or anything, but she and I just sort of had this vibe despite being so, so different in so, so many ways.

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Fast-forward … I don’t know how long, but fast-forward nonetheless. There came to be a time when we were pretty open about our feelings for each other, feelings that had developed in ways that we didn’t quite understand … and also feelings that were quite safe given the distance between us. It was fun to have a long-distance romance of sorts. Our letters became more frequent. We’d write back as soon as the other’s letter arrived and drop our missive in the mail the next day. Then, we decided we’d write whenever we felt like it, which meant we didn’t necessarily wait for the other person’s letter to arrive before sending a new note across the country.

Soon, those letters were augmented with phone calls, though they had to be infrequent and in the evenings because, kids, there was a time when long-distance phone calls cost a shit-ton of money per minute and were slightly cheaper after 5 p.m. We also didn’t have Starbucks, remote controls or drive-thrus. And we walked to school up hill both ways — in the snow, you freaking Instagram pansies.

Those calls were fun. Every once in a while, they’d last multiple hours and stretch from one night into the next day. I’d open the window to my bedroom, climb out on the roof while dragging the phone cord, and lay there on the slanted shingles staring at the stars and the moon — the same stars and moon that she was seeing so many miles away.

Yeah, I was that sappy. So was she.

We shared a love of music, and we’d send mix tapes across America in the mail, and also held the phone up to the speakers from our boom boxes if a new song we liked came on. We were big into power ballads back then, and somehow, Skid Row’s “I Remember You” became “our” song.

It was cheesy. It was hokey. It was everything that growing up in the 1980s was supposed to be.

But it wasn’t all sunshine, roses and sweet, sweet songs. Jill was most definitely a teenage girl and had her moments. There came a time around the start of a school year — my junior year, if I remember correctly — in which all the letters seemed to slow down, at least from her end. Then they stopped.

Months went by, and for the first time in a while, there was no Jill in my life. I didn’t know why. I didn’t know what I’d done. She wasn’t answering my inquiries. I had been ghosted before ghosting was a thing.

And then Christmastime came around. I just wanted to know why. So one night over Christmas break, I worked up the courage to call and ask. Revolutionary concept, right? But when you’re that young and that confused and that much of a feeler, it’s hard to dial those 10 numbers (and don’t forget the 1, kiddos) and actually be on the line when it starts to ring.

This time, however, I was, and when I heard her voice, I realized I couldn’t speak. I tried. I couldn’t.

That was, of course, problematic. So I did what I could … I started playing a song from a CD that was in my super-boss six-CD changer. When it was over, she was still on the line, and I heard her crying softly. But I still couldn’t talk. So I played another song.

Eventually, a song ended and my voice was there. I said, “Why?” And through sniffles, she said how sorry she was. She didn’t know why she’d done it. She said she’d just felt confused and overwhelmed but that she was so, so sorry. By the time the call ended in the early hours of the next day, we were back to being whatever it was we had been before, and it was good.

The next day, a letter from her arrived in the mail.

I was confused. Thoroughly confused. How could a letter get all the way across the country in less than 12 hours? When I opened the letter, I realized … this letter had been sent before my phone call.

So I called her back.

“You didn’t tell me you sent me a letter,” I said.

“Wait. You didn’t call me because you got my letter?” she replied.

“No! I had no clue you’d sent a letter. I called because I missed you.”

We took this odd coincidence to be a sign from above that the two of us were meant to be in each other’s lives. I don’t know what I think about that today, but I do know that re-establishing that link is responsible for so many of the good things that happened in my life.

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Back in the day before the internet, we searched for colleges from massive, encyclopedic books listing all the schools in the country in entries with impossibly small type and details about things such as the student body size, the percentage of Greek students, retention rates and the like. Through those entries, we developed our lists of schools and sent away for more information, which would arrive weeks later in the mail.

This is where myth and fact cross in my life. The myth as it’s told by my parents and others in the know at the time is that I selected Drake University because of its proximity to Jill. And for awhile, I let that myth be the story that was told as fact.

The truth is something a little different. The truth is that I never looked at a school closer to my home than Indiana because of some very good reasons that had nothing to do with Jill. I needed desperately to get away from everything that I’d become familiar with and what was an incredibly poor relationship with my mother. In essence, I needed to be me, free from all the drama that had surrounded me growing up.

So one night, during a time in which my sister wasn’t secretly wishing for my death, we sat in my room with the Big Book of Colleges in front of us. I had already started my journalism career, and I knew I wanted to go to a college that would let me take journalism courses straight out of the gate. I also wanted to be able to get involved in the student paper immediately.

“Wouldn’t it be funny if you went to school in Iowa near Jill,” said my sister.

“Yeah, that’d be funny!” I replied.

So she looked up journalism schools in Iowa that had a smaller student body and a smaller percentage of Greek students. Drake University was one such school. She read me the entry, and it sounded good.

We sent away for information, and when it arrived, there definitely was nothing to cross it off my list.

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My father and I played a trip during spring break of my junior year to go see some of the schools on my list. We were going to fly to Des Moines, see Drake, rent a car and drive east, stopping at schools such as Bradley University, the University of Evansville, Valparaiso University and more. I casually let Jill know that I’d actually be in her home state on a certain day, though I had no expectations of seeing her. She lived a good hour from Des Moines.

We landed in Des Moines, and as we descended the escalators in the airport, I saw her. Jill had blossomed from an awkward young teenager into a beautiful older teenager. I’d seen that in the photos she’d send me from time to time. But seeing her in person? It was next-level.

We hugged awkwardly, and our families went out to dinner that night before we said goodbye with another awkward hug and my father and I continued with our college tour. The next day I went to Drake, met the professor who would help change my life, and I set the school as my top choice.

There was this thought from everyone in the know about Jill and I that when I arrived in Des Moines, this fairy tale would march inexorably to the aisle of a church where we’d someday be married. I don’t know that I shared the same enthusiasm for that narrative, but it was a good story and I always dug a good story, so why not?

The problem was that, well, when it came time for what had been a long-distance relationship to perhaps turn into something real, Jill didn’t want it. She would tell me at that time that she was going through a phase, that this was just really hard. And I told her I understood. Part of me did. It’s something entirely different from a fairy tale when Prince Charming comes across the country and suddenly is real and might not be or look like what you’d hoped he’d be and look like.

And so before classes even started at Drake, Jill and I went our separate ways.

A week later, I met the woman who would become my wife.

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If not for Jill, there is no wife and life as I know it today. Jill — everything we were, everything that led me to even consider a school in the middle of freaking Iowa — set me up to meet the most important person in my life. And so there had to be a Jill for there to be a me like I am today.

There was a time I thought Jill would one day be my everything, and when she told me of the phase she was going through and it became apparent she wasn’t that into real-life me, it hurt. But I got back up and moved on. I hadn’t gone to Drake for Jill. I’d gone to Drake because it presented me an opportunity to learn what I needed to learn to be a good journalist.

So I did that. And I met my wife. And we’ve made an amazing life together.

It’s a life I know I wouldn’t have had without Jill, and so, for that, I am grateful.

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Jill and I? Our lives would collide from time to time as the years rolled on. She called me one day and told me she was coming up to Drake to look at the school. I told her that was nice. When she offered to meet, I declined.

Then, she called one day to tell me she got accepted to Drake’s pharmacy program and would be starting in the fall. I again told her that was nice.

The last time I saw Jill was on a rainy day in the spring of my senior year in college. I’d become engaged the previous September and was looking forward to graduating and starting my professional journalism career. She’d called me to ask if we could talk. Sure we could talk, but I wanted it on neutral territory, so we met at a nearby park as the rain pounded down.

We walked around a lake under umbrellas. She was sad but happy for me, wondering what exactly had happened to the friendship we’d had and why it was that we couldn’t still talk from time to time. I told her that it was just awkward and difficult and that I wished her an amazing future. Then, we said goodbye.

Over the years, I’ve seen that she, herself, got married, had two kids, became a pharmacy manager, lives just outside Des Moines. I’m happy for her. I’m glad she has made a good life with who seems like a good man and has kids who seem to be good kids.

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So yes, I think each of us can look back on our lives and see the dot connectors, the setup people who helped us get from where we were to where we need to be so the full picture can be made.

An improbable meeting in the middle of nowhere in Texas.

A girl from Iowa.

A boy from New York.

Lax data privacy.

Letters. Mix tapes. Phone calls.

The Big Book of Colleges.

Everything leading me toward my wife, to my boys, to the life I know and love today.

So let’s raise a glass to Jill, a wonderful setup person, an amazing letter writer and stargazing companion, a kind soul who was free with her heart and who made the effort to find that geeky weirdo from New York she met on vacation. Had you not taken that step, Jill, I don’t know where I would be today. To you, I raise a glass and give you a toast, to thank you for being a really, really good setup person and dot connector. Hear Hear!

Who should be the next Living Eulogy? Email me at johnagliata@gmail.com.

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