“Are you happy?” She asked me.

It’s been nearly two years since I reached the end of 10 Cities/10 Years. My first year in New York came to an end, and a second one started with little fanfare. I had girded myself for a come down period, but I wasn’t prepared for it to come so soon, or so brutally. Apparently, ten years of moving had trained my body to crave change and it didn’t react well to being deprived.

It was the deepest mental crash I’d experienced since New Orleans, triggering a complete emotional and physical exhaustion. My first year in Brooklyn had been exhilarating, but now everything curdled in my vision as I felt walls closing in. For the first time in my adult life, I didn’t have a goal. I needed purpose.

One Last Story

We barely spoke to each other as Ruth drove me back to my Bed-Stuy apartment. This would be her first time coming to my neighborhood with me. She wasn’t staying. We pulled up to my front door, parking briefly. I leaned over, kissed her goodnight, and then, before opening the door, paused.

“This is over, isn’t it?” I asked.

We met on a dating app.

A week after I moved to Brooklyn, I downloaded the Tinder app to my phone. A week later, I went on my first Tinder date. That woman cheerfully offered to give me a tour of Brooklyn. We walked around on a drizzly end-of-summer Saturday, had a few drinks, and exchanged the details of our lives. It was the prototypical first date.

Our second date was a concert. We had a pleasant but unspectacular time before kissing goodnight. Then she went out of town and when she returned, she texted me that it wasn’t a good time for a relationship (I later learned this was a common dating trick: use a trip out of town to ghost an unwanted date). I said I understood and moved on. I ignored the app for another year.

It was a couple months after Sophie left that I tried Tinder again. As it turns out, my life is great fodder for casual conversation – one Tinderalla called it “the perfect first date story,” and she had a point. If a conversation was stalling on a date, I could turn the subject to some city I had lived in and it would open up all new avenues.

Dates came in waves. Some weeks, I saw two or three different women, and other weeks all matches went ignored. There were numerous first dates, a smattering of second ones, and on a few occasions, I made it to a third. The fourth remained out of reach. It got to the point that getting past the third date seemed like a milestone.

I’m certainly not the first person to feel that dating apps essentially make a game of the whole endeavor. With each fleeting connection, as the fourth date grew more elusive, it started to reinforce that game mentality, with each date feeling like a level to be reached and beat. There was a goal to be achieved. But I kept dying at the same spot. Reset.

Though a lot could certainly happen in between a first and third date, I convinced myself that what I wanted – a lasting relationship, a reason to stay, a purpose for a life in Brooklyn – waited right on the other side.

Yeah I was losing, but I was having fun playing all the same. There were good conversations, making out, even a couple one-night stands. Some connections felt more substantial than others, and it was disappointing when they fizzled out. Trysts were a nice enough distraction, but I was, perhaps naively, hoping for more. I’d spent the previous decade ricocheting between wildly impractical love affairs and loneliness. I was ready to try a stable relationship. Didn’t I deserve one?

I decided to expand my pool of dates by downloading Bumble, an app practically identical to Tinder except that it requires women to start the conversation. It appealed to my shy nature and I appreciated that it gave women more control. I’ve seen enough Tinder Nightmare posts to feel bad for every women, ever. The connections on Bumble were, indeed, better. It was harder to get to the first date, but when I did, it didn’t feel like we were wasting each other’s time, even when it didn’t go anywhere.

I connected with Ruth on Bumble in June. For our first date, over drinks and appetizers, we talked literature and our different upbringings – she grew up in New York City and had lived there most of her life – and when the night was over, I walked her to her bus. Our second date was a sushi dinner in Brooklyn Heights. Afterwards, we walked along the Promenade and kissed in the glare of passing traffic.

Our third date took place at a Celebrate Brooklyn concert in Prospect Park. She arrived fifteen minutes late, and partially into the date, one of her friends joined us. This felt like a signal, the brush off, so I was surprised when she proffered an invitation to her Cobble Hill place following the concert. The next morning, we made tentative plans for a fourth date.

As that night approached, I anticipated a text saying she was sick or she had to work, any of a dozen excuses I’d been given by past connections. Instead, she arrived (late) for dinner. The date itself wasn’t particularly interesting – we saw a movie she didn’t enjoy and then returned to her place – but we had reached a fourth date. It felt momentous.

More dates followed, usually ending at her place. I met her friends and her parents, even attended her father’s poetry reading. She went out of town for a week around the 4th of July and when she returned she didn’t blow me off. She had me over on a particularly scorching Wednesday night and cooked us dinner. My friends, who hadn’t met Ruth, took to referring to her as my “girlfriend.”

The following Saturday, we returned to Prospect Park for another concert. She was late again. From the moment she arrived, I could sense her absence. I knew she had just received some upsetting family news so I chalked it up to that. Back at her place later that night, though, she turned to me and confessed in her matter-of-fact way, “I feel ambivalent about you.”

She clarified that she wasn’t disinterested, just uncertain. She had strong feelings about me in opposite directions. I suppose she thought that would be reassuring. As best she could articulate, my best quality appeared to be that I was “nice.” Never a good sign.

We hashed out our feelings for maybe an hour and the next morning the tension had dissipated. We went to a neighborhood coffee shop to work next to each other. If felt like a couple thing to do. I’d started to relax when, as we walked back to her apartment, she stopped in the middle of the sidewalk and said, with a pitying smile, “I don’t want you to worry about how I feel.”

Yeah right.

We didn’t talk again until Thursday night when I received an unexpected call from her. I’d spent the week bracing for her to end things, so I was shocked when she invited me to join her and a group of friends for a weekend trip upstate.

The weekend was almost perfect. There was swimming in a pond and climbing waterfalls. We cooked BBQ and drank, roasted s’mores and played games. Group conversations covered religion, politics, and art. The trip felt like a turning point; Ruth appeared to be giving me admission into her group of friends. It was somewhere to belong.

And yet, I could still sense it: Ruth’s ambivalence.

The next weekend, we went to see Louis CK perform (this was well before the accusations of misconduct were public). She picked me up, arriving early this time, and drove us to the show out in Forest Hills. On the way, I noticed her respond to a message on Bumble. Ruth’s distance was palpable – while waiting in line, I tried to hold her hand and she pulled away. We both laughed heartily through Louis’ typically brilliant set, even as he touched on the uncomfortably relevant topic of doomed relationships. 

She took me home – she had an excuse for why I couldn’t come over that night – an interminable drive. Sitting mostly in silence, I spent the time working up the nerve to ask the question I knew would end our nascent relationship. After I asked her if it was over and she answered in the affirmative, we talked for another ten minutes, exchanging only a few words. While she didn’t feel strongly for me, she couldn’t bring herself to break up with me. I had to break up with myself.

“I don’t want you to be sad,” she said as I prepared to exit her car. I almost managed a grin. She had never had a say in that.

We’d only been seeing each other a month and a half.

I was, of course, sad after the break up, but not devastated. Even in the moment I could recognize that we had never really clicked as a couple, and that I had placed undue weight on the relationship because of that arbitrary fourth date milestone. I was rushing towards a fabricated resolution because I wanted there to be an endgame.

Ruth was a smart and funny woman, independent and focused. She had her failings, everyone does, but they were irrelevant. She was a reminder of the greatest gift that 10 Cities/10 Years had given me: a surplus of remarkable, strong women in my life. So many, in fact, that in these chapters, I’ve barely scratched the surface. There are so many more stories left untold.

I count myself incredibly lucky for all the women who have come into my life, some for only a matter of months (or days), others for years, and maybe even life. Their perspective has changed me for the better, their support sustained me, their creativity, grace, and beauty invigorated me when I had lost the will to continue. 10 Cities/10 Years was a journey from boyhood to manhood, and women were my guide.

A couple months after Ruth exited my life, my travel companion, Emily, and I took a trip to Spain together. I had a revelation. Upon returning to the States, I deleted Bumble. I resolved to forgo dating for the next year in order to save for a move abroad, a decision that was met with some skepticism by my friends. But if there’s one thing more enticing to me than love, it’s the road.

I thought that when I reached New York I would feel a sense of place, of purpose. I believed that the city would be a star of too great a gravity to escape, that I would finally find a home. And I do feel at home in Brooklyn, I do feel a sense of belonging. Maybe I could be happy and in love here. Why not?

But I haven’t reached the end of the road.

Now I get asked a lot, “What’s the plan?” How long will I be in Spain? What will I do after that? When will I come back? The answer, to all questions, is, I don’t know. There isn’t a plan this time; no goal, no purpose. I’m going because it’s where I want to be right now. That’s enough.

I’m not looking for a destination, anymore. It can find me if it wants to.

“Are you happy?” She asked me. This woman who had been the center of my world at one point had all but vanished from my life. We hadn’t spoken in years. She has a good life now, a happy one. The life she deserves. I may never be a part of it again.

I couldn’t answer her question. I’ve never been able to. The answer isn’t yes or no, it’s a treatise.

I’m alive. For however long as that’s still true, it’ll suffice.

Read the whole book.