My Online Date Rejected Me. When He Asked Me Out Again 17 Years Later, I Was Shocked By What He Told Me.

The author, a few months before she met John in 2001.
The author, a few months before she met John in 2001. Photo Courtesy Mary Christine Kane

It was a song that hooked me. “Boots of Spanish Leather,” a lesser-known Bob Dylan track I’d been playing on my Volkswagen tape deck obsessively — the Nanci Griffith version. I mimicked Griffith’s twang and bounced in and out of singing with her. It’s a song of love and the end of love.

I liked both parts — love’s rising and falling. Maybe because even at 30, I had felt love’s sorrow. The lyrics reminded me of how much I longed to be in love, to have my own someone to sing to.

The song was Owen1170’s online dating headline. I’d soon learn he preferred the Dylan original. To see him name the song, my heartfelt obsession, made me feel in some way already known.

I was new to online dating, but his profile seemed great. His picture showed a blond-haired man with his eyes half closed, his long fingers strumming a tuxedo guitar. He liked reading and live music. He had played hockey for Notre Dame and had a graduate degree. Like me, he had never married or had children but wanted both. 

After a few emails, Owen called and confessed in his deep, melodic voice that his name was John, not Owen. I could call him either. He liked the name Owen; he was hoping it would catch on. I called him John. 

We met at a movie theater between his Uptown Minneapolis apartment and my nearby suburban home. He was just as cute as I had hoped. He looked like an urban cowboy in a Western shirt and boots. At the end of the night, he asked me out again. I Scotch-taped the ticket stub into my journal. 

Our romance was cat-and-mouse. I was the cat; he the mouse. We would have a great date and then I wouldn’t hear from him. Later he’d say he’d been busy at work. He co-owned a business, where he’d often stay until 1 or 2 in the morning. It was easy to think: Maybe it isn’t me, maybe he just really loves his work.

Still, it wasn’t a big surprise when at the end of three months he revealed that he couldn’t see himself with me long term. His explanation was that it bothered him how much I liked camping and how he had to drive to the suburbs to see me. He said he was looking for more of an urban gal. I told him the word “gal” was very un-urban.

It was difficult reconciling the news with my feeling that we were destined to be together. What about the song? It got played many more times as I tried to accept John’s news, feeling rejected and lonely.

A week later, I saw him while driving Highway 94. I honked and waved, my adrenalin kicking in so that I became shaky. A few weeks later, on that same stretch of highway, I saw him again.

Those encounters marked the beginning of a 17-year era of running into each other. More than 3.7 million people live in the Minneapolis-Saint Paul area. Of course, it’s normal to run into people occasionally, particularly if they live in your neighborhood or you run in the same crowds. Neither was true for us. We had a built-in magnet for each other. 

Often we’d see each other walking downtown or uptown. When we could, we would stop and chat. Each time got a little easier for me as the sting of the rejection dissipated. Sometimes months would pass between encounters. Other times years.

We both ended up at a French restaurant once, when I ducked out of a painfully boring date and he gave me his sympathy. Once, unknowingly, we were both working in downtown Minneapolis when a building got locked down with rumors of a gunman. I went to investigate. The journalists were there, the police, the fire department. And also, of course, John.

By this point, I wasn’t pining over him any longer. The more I got to know him, the less convinced I was that we were a good romantic match. But, I still wondered, as did my friends, WHY DID THE UNIVERSE KEEP PUTTING US TOGETHER? Were we MEANT for each other?

One wintry night I was sitting by a window in a coffee shop when he walked by. I recognized his blue knit cap with the white stripe and his winter walk — hunched over but still with a bounce. A few minutes later, he stood before me. This time he seemed nervous and left quickly. Soon after, I got a text: I’m married now. I can’t be hanging around with ex-girlfriends. It was good to see you. 

I was hollowed out by the sound of our door clicking closed. My lingering idea of us being destined for each other had to be forgotten. It felt even more lonely to know there was one more person in the world paired up, a person who had rejected me, and I was still alone.

Four years passed until I saw John again. I was living alone in the four-bedroom home my fiancé and I had bought for us and his two children before he changed his mind, explaining to his children we were a puzzle that didn’t quite fit together. The house was so empty it echoed. I spent most of my time in the basement with my cat, sinking into the couch and Netflix shows. 

The author and her Volkswagen, where she used to listen to “Boots of Spanish Leather,” in 2016.
The author and her Volkswagen, where she used to listen to “Boots of Spanish Leather,” in 2016. Photo Courtesy Mary Christine Kane

One evening after work, as I stepped onto the 4K bus on the way back to that empty house, I saw John in row eight. We smiled at each other like, There you are.

It was a comfort to sit next to John and tell him about my breakup, the house, Netflix. He told me about his divorce. He told me something else I wasn’t expecting. He had wondered, he said, even through his marriage, if I was the one who had gotten away? I saw our door slowly open again.

John expressed his interest in dating me. I was flattered and lifted by his enthusiasm. I was also in one of the messiest periods of my life. I wasn’t ready to date anyone yet. Would the door click closed again before I was ready?

Soon after, alone in the dark in that big empty house, I opened my email to a song John sang and recorded for me, ”With or Without You” by U2. It’s a beautiful but aching song of someone waiting for his love, just like Dylan’s song. He had become the cat; I was the mouse.

Hearing John’s beautiful voice and the simple guitar fill my dark house, knowing he sent it because he cared for me, unbolted some of the sorrow from my chest. I cried myself to sleep.

Every time I saw him I would wonder, was it the last time? Was our business settled? It never was. 

I was in Uptown saying my goodbyes to two girlfriends and I saw him crossing the street toward me. He was going to get some dinner,would I like to join? 

Sitting with him in an outdoor restaurant on a pretty June night with a light breeze, I felt happy. I thought of how much of each other’s lives we had already witnessed. How I had learned that when he eats he takes big enough bites that his eyes scrunch. He always orders what he wants and never worries about cost or calories. He’s a good listener, although his memory of the past is vague. He takes every question seriously and answers it fully. He still wears his cowboy boots and Western-style shirts. 

A full 17 years after we first met, he asked me out on a date. I said yes.

We had dinner at a trendy restaurant and played a few flirty games of foosball after. We went back to my place and he played my guitar, just like old times. Then we made out on the couch, also like old times. He held me and I felt like I was being held by someone who truly cared about me. When he left, I floated off to bed.

The next day, he didn’t call. Or the next. When I finally called him, he apologized, said he’d had a great time but had been very busy at work

After some prodding he also said, Driving away from your place, I didn’t like how I felt being in the suburbs. I think I need to date someone more urban.

Really? There it was, almost verbatim the words he had said to me 17 years earlier. Our relationship was like a shirt that you buy and love at first but then never wear because it’s just not quite right, although it’s hard to say why.

In ”Boots of Spanish Leather, Dylan sings “take heed” three times, something I hadn’t noticed when I was first falling for the man with the long guitar fingers and melodic voice. Take heed. Isn’t that always good advice for love, no matter what form it comes in? 

The author with her partner Steve, visiting a Wisconsin farm in 2022.
The author with her partner Steve, visiting a Wisconsin farm in 2022. Photo Courtesy Mary Christine Kane

Soon after our last date, I fell in love with someone else. Someone who had also been circling my city my whole adult life but who I had never previously met. It seems my electrons have realigned to him, as I haven’t run into John in six years now. 

Now I think the universe put John and me together not for a romantic destiny, but because we needed each other in a different way. Seeing him always lifted my spirits, often at times when they most needed lifting. I think it was the same for him.

I have a feeling I won’t see him again, since John and I now are clear that we aren’t a romantic match, and I will miss our run-ins. But who knows — the universe is full of surprises. Maybe we will run into each other one day in an assisted living facility. If we do, I know it will make me happy. Maybe we can listen to our song together.

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