How I Knew I Was Really a New Yorker

Kate Eberle Walker
5 min readMay 5, 2020


It was my first year in NYC. I went to a party that my friend Amanda Blum threw on the Upper East Side and I met a guy. His name was TJ and he played football in college. Turned out, he lived in a really big doorman building on 95th St, and I lived in a really big doorman building on 96th St. On our first official date he wore a light blue cashmere sweater with a zipper collar. He worked in Mayor Giuliani’s office.

On our second date I was extremely excited to learn that the very next day the mayor was doing a promotional event with Debbie Gibson, and TJ was responsible for being her point person throughout the day. Debbie Gibson was my ultimate teen idol. Ten years prior, her hit single Foolish Beat had been at the top of the charts. I had watched the music video hundreds of times, soaking in the images of her walking the cobblestone streets and seaport docks of New York. These were places that I now knew, five months into my own New York experience, were places no young woman walked alone at night, even when mourning the loss of a true love to the accompaniment of a moody saxophone sequence.

When TJ dropped me off at my apartment at the end of the date, I asked him to wait while I went to my closet to grab my cassette tape copy of Debbie’s seminal album, Out of the Blue. Most of my childhood belongings remained in boxes in my parents’ garage upstate, but Debbie came with me to New York. I gave the tape to TJ so that he could ask her to autograph it for me. The next night I couldn’t wait to see him and hear about the day, and to see the amazing personal note that I imagined she might write me. He would be spending the entire day with Debbie, so he could tell her all about what a big fan I was. She would probably love that, and write me something really perfect, because Debbie would be so good at connecting with her fans. And, how New York was this? Dating someone who worked in politics and interacted with famous people!

The next night, TJ invited me to come over to his apartment for our third date. It was a Thursday night, and we were going to stay in and watch the new episode of Friends with his roommates. I arrived, and was a little thrown off when he didn’t immediately start telling me about his day with Debbie. He didn’t mention her at all. We made spaghetti, sat down in the living room to watch the episode, and I tried to play it cool but basically the whole time I was thinking WHAT ABOUT DEBBIE?!?

After the Friends episode ended, he suggested that we retire to his room. He probably had something on his mind other than Debbie Gibson, but I was ready to finally get into the details of his day with my teen icon. As soon as we were alone, I asked him about my Debbie tape. He looked confused, and after a pause, said

“Oh! Right. Yeah it was a really busy day, I didn’t get a chance.”

He went and retrieved the tape, from the pocket of the khakis he was wearing the night before when I gave it to him. He hadn’t even brought the tape with him to work that day. I came to the realization that my cassette copy of Out of the Blue had not been in the vicinity of Debbie Gibson that day; it had remained, forgotten, in the pocket of yesterday’s pants.

I shrugged and walked toward the door.

“You’re not going to stay?” TJ asked with confusion.

“No,” I said, equally perplexed that he’d think I would stay.

“Should I call you tomorrow?” he asked.

“No. I mean, we can’t date now,” I continued, stating what was obvious to me.

“Because I didn’t get your Debbie Gibson tape signed?” he asked slowly, clearly questioning my stability at this point.

“Well yeah.” I said, matter of factly. “You were supposed to think that it was adorable and quirky that I loved Debbie Gibson so much that I had brought her cassette tape with me to my first New York apartment. And that it was so amazing that you happened to be in a position to do something for me that I would uniquely love. You would have come up with some outlandish thing to ask Debbie to write to me. You would have thought it was fun.”

He started to get indignant.

“That is crazy,” he said. “I had to do my job. I was just too busy today.”

I shrugged.

“I get it. I do. But I still want to find that guy who would have gotten Debbie Gibson to sign my tape.”

And I left.

A month later, at 8am on a Tuesday, I squeezed onto the subway at the 86th street 4/5 station, having run to catch the transfer from the 6. Once the door closed, I realized I was pushed up right against TJ. Much too close to just pretend I didn’t see him.

“Oh hey!” I said with my best impression of cheerful surprise. “How are you?!”

I realized, since he worked at City Hall, we were both on this train for the long haul, all the way downtown. He knew it, and I knew it. We made awkward chit chat for a few minutes and then stood next to each other in silence for about 16 more minutes. As we pulled up to his stop, he turned to me and said,

“Hey sorry about that Debbie Gibson thing.”

“Oh,” I said, pretending I had forgotten all about that silly thing. “it’s cool.”

But we all know it wasn’t cool.

He got off the train, and I smiled as the train proceeded to my stop at Wall Street. I thought, getting trapped next to your ex on a crowded subway during rush hour is the kind of thing that would only happen to a New Yorker.



Kate Eberle Walker

CEO of PresenceLearning and Author of The Good Boss: 9 Ways Every Manager Can Support Women at Work. Mom of 2 girls. @eberlewalker