Bookstore Date Guy
“In a world of bare minimums, be the person who makes an actual effort.”
- Me. I wrote that for this blog post…cause there was nothing else that worked.
If you're around my age, you might find today’s dating scene particularly frustrating. We remember a time before social media, before apps, before the information overload that makes us constantly check in and out, chasing the illusion of endless options. Dating has shifted from sweet phone calls and thoughtful gestures to navigating a sea of “u up?” messages and ambiguous situationships.
Recently, while mindlessly scrolling through my Instagram feed at a bus stop, I stumbled upon a familiar name and a not-so-surprising post—a man I’d dated several years ago had shared a picture of a woman’s slender hand, elegantly holding a wine glass and adorned with a delicate engagement ring. In that moment, I realized I had yet to tell the story of the man behind that proposal.
Let’s rewind a few years to pre-COVID 2019. I had just landed my dream job and was mere months away from achieving something I once thought impossible—my first shiny degree, with honors. It was January, and the combination of career success and academic achievement had me riding a wave of optimism in New York City.
Buoyed by this positive momentum, I decided to dip back into the dating app scene, hoping that good fortune would strike in threes and lead me to my next meaningful relationship.
Enter Daniel. He was the embodiment of mid-century modern charm: tall with perfectly combed hair styled in a side part, his clothes tailored to frame his lean physique. There was something about his look that reminded me of Clark Kent, always ready to jump into a phone booth and save the day.
Like me, Daniel had a love for The Met and sometimes volunteered there to give tours. He was also an adult student who had paused his career to go back to school for something entirely different from his previous job. On top of that, he had just gone through a divorce the year before. I was hopeful that, amidst the significant transitions in both our lives, we might find a meaningful connection through our shared experiences of change.
One evening after a week or so of chatting, Daniel offered to meet me outside of my school for a walk, and I eagerly agreed. Dressed unusually well for my class on international policy, I stepped into the crisp winter air after class, anticipation flopping about in my chest.
Daniel looked dashing, straight out of a dream, standing under a streetlight with a half-smile. He wore a long camel-colored coat and dark-rimmed glasses, and as we hugged, I caught the faint whiff of cedar.
"I know you also love books," he said as we started walking in what seemed to be a random direction. "So I have a fun first date idea."
I raised an eyebrow in curiosity.
“We’re going to the Strand,” he continued. “When we get there, we’ll buy each other a book, read them, and then meet up to discuss what we felt.”
Despite the January chill, I felt warm. A bookstore date? After enduring countless low-effort New York dates that mostly involved getting wasted over cocktails, this felt like a breath of fresh air. Perhaps he really was a dream.
For those of you who aren’t New Yorkers, let me take a moment to break down The Strand. A bookish institution since 1927, The Strand was built along what was then called Book Row in Manhattan—a six-city-block stretch that once housed forty-eight bookstores (insert swooning sigh here). Nearly 100 years later, The Strand carries over 2.5 million new and used books, boasting 18 miles of books. It’s beautiful, unpretentious, and the king of New York’s independent bookstore chains. A bonus fun fact: I met Salman Rushdie there one year on my birthday.
We walked the few blocks to the store and then both got lost inside, promising to find each other once we had chosen a book for the other. I won’t lie—there was an element of pressure. While we had discussed books before and I had an idea of his tastes, selecting the right book for a first date felt significant. Should I pick a personal favorite like The Hobbit or Harry Potter and risk him thinking of them as children’s books (don’t come at me—I know they’re not)? Should I go for a classic like All Quiet on the Western Front? Or perhaps choose something metaphorical and profound?
In the end, I leaned towards the latter, considering that he was also navigating major life changes similar to those I had experienced.
I scanned the shelves and found myself drawn to The Alchemist by Paulo Coelho. Cliché? Perhaps. Brilliant, nonetheless.
I turned to see him waiting at the front of the store, watching me with a smile. I waved him away to keep the surprise, checked out, and then we walked to a nearby whiskey bar aptly named The Library.
We settled next to each other at the bar, our knees brushing softly, and ordered drinks. My pulse quickened slightly as the familiar scent of cedar wafted through the air.
“Are you ready to do our swap?” he asked, his expression serious and focused, as if he was absorbing everything around him.
I nodded, grabbing my Strand bag and handing it to him while he handed me his.
I pulled back the plastic to reveal Just Kids by Patti Smith.
“Have you read it?” he asked, studying my reaction.
I smiled and shook my head. “No, I haven’t.”
“This is one of my favorite books about New York,” he explained. “It changed the way I look at the city. Do you know who she is?”
“Somewhat,” I answered honestly. I knew she was a musician from when my parents were young and wild, but that’s all I knew.
“Great, then you’ll get to know her too,” he continued. “She had a long relationship with the photographer Robert Mapplethorpe. You’ll learn more about both of them.”
“I can’t wait,” I said. I was still very much in that phase of seeing everything around me in New York through rose-colored glasses—even the rat that had just scurried past me on my way to class earlier that night.
Daniel pulled my book for him out of the bag and grinned. “I’ve heard of this book.”
“You haven’t read it though, right?” I asked, a hint of panic in my voice.
“No!” he reassured me, laughing. “Don’t worry. I just know of it.”
“Great,” I replied. “I know it was the ‘thing’ a decade or so ago, but this book really moved me when I felt all jumbled up and confused about what to do with my life. It changed how I make decisions. I thought you might appreciate that.”
A wave of nostalgia hit me—how reading that book and Coelho’s foreword still affected me to this day. If you haven’t read his reflections on the phases that come with following one’s life dream, it’s well worth the effort. Without those words, I might have given up in New York long before I reached this point.
“I think I might,” he agreed, his intense stare locking onto mine. I could tell he was someone who wore his heart openly, capable of feeling a complex array of emotions. I hoped he’d continue looking at me with that same intensity.
We ended our date with plans to meet again in a week, and he surprised me by going in for a kiss when I went in for a hug. Despite the initial awkwardness, his lips on mine warmed me against the cold winter air on the sidewalk. He was steady and gentle, but his hand pulling me closer with his hand on my lower back told me we were both eagerly anticipating our next meeting.
While I waited for our reunion, Patti and Robert kept me company in Just Kids, revealing a side of New York I had never seen in such vivid detail—one of rock 'n' roll, artist gatherings, and apartments without bathrooms. I immediately related to Patti, with her intense passion for living in New York and following her dreams, knowing she was destined for something important. I played "Because the Night" and "Dancing Barefoot" on repeat and pored over Mapplethorpe’s photos obsessively.
One day, while walking to an art supply store to buy paint for a painting I’d been contemplating, I looked up and was surprised to find myself directly across from the Chelsea Hotel—a beautiful red brick building on 23rd Street that once housed some of the most famous creatives of the 60s and 70s, including Patti and Robert. For a moment, I felt like I was seeing the street through their eyes.
Every street and alley seemed to have a whole other layer of history. Few books have impacted me the way Just Kids did, and I still think fondly of the moments and stories it shared. When I finished the book and it was time to meet up with Daniel, I was excited to share my reflections.
That following Tuesday, we found ourselves at a cozy bar in the Seaport, ready to discuss the books we’d exchanged. I was thrilled—not just to share my thoughts, but also to be near someone who appreciated a book like this.
“So?” he asked, anticipation in his eyes.
“It was brilliant!” I gushed. “The insight into the Chelsea Hotel, their love story, all of it. New York in that book doesn’t exist anymore, and I felt like I was stepping back in time, seeing a layer over this city I love that I’d never seen before. Somehow, it made me love New York even more.”
He beamed, clearly pleased with my review. “Yes! It was a really meaningful book to me.”
“Okay, you’ve heard my thoughts,” I continued, suddenly nervous. “Your turn.”
Daniel sighed, his smile fading. “It was good. It definitely made me reflect a lot on my own life.”
I waited, noticing he wasn’t brimming with excitement like I had been. Had I chosen the wrong book?
“The crystal merchant,” he began, referencing a character who symbolizes someone who doesn’t pursue their dreams and feels empty, surrounded by fragile things. “I related to him.”
I wanted to shake my head and say no—that as someone who had gone back to school to pursue his passion, he should relate to the protagonist who went after his dreams. But I waited, letting him continue. His story, after all, wasn’t mine to define and
“I just liked how he stopped while he was ahead and felt safe,” he explained. “I feel like my ex-wife was more like the protagonist, always chasing big dreams and taking big risks. And that wasn’t great for us.”
Ah, there it was. Daniel's dissonance with the story stemmed from his recent divorce with his ex-wife. I paused, struck by how profoundly personal our connections to literature can be—each of us carrying our own narrative baggage, shaped by past relationships and life choices. Until then, The Alchemist had been a beacon of inspiration for me, urging me to pursue dreams with unwavering determination and I assumed it would be the same for others. Yet, Daniel's perspective added a new layer, reminding me that stories resonate differently depending on where we stand in life. For the first time, I found myself questioning whether this gentle man had truly moved on from his past relationship.
Despite the subtle shift in his demeanor, our goodbye lingered with an unexpected intensity. The kiss extended, his arms drawing me closer, leaving me a little out of breath. There was a maturity and respect in his gestures, intertwined with a hint of passion. In that moment, I felt a surge of hope—perhaps there was something here.
A few days later, Daniel asked me out on our next date, and true to our shared love for The Met, he planned for us to visit the museum. Despite my initial hesitation, mindful of his reaction to the book and knowing that The Met held memories of his proposal to his ex-wife, I trusted his judgment about where he was.
Leading up to our date, I noticed his messages becoming less frequent. He assured me it was due to upcoming exams, and I trusted him. I felt comfortable knowing we had a date planned later in the week.
He met me at the museum’s main entrance, looking every bit the dapper Clark Kent. His smile was warm as he leaned in for a kiss, but there was a subtle shift in his energy, a hint of something missing. I attributed it to exam fatigue and chose to set aside my concerns, eager to enjoy what promised to be a fun date.
Exploring The Met—a museum I'd always longed to visit—with Daniel, who expertly guided us through its halls, was truly a dream come true. First, he led me to the spot where you can see the original facade of the museum's first iteration—a red brick structure visible from the Robert Lehman Wing. Then, we marveled at John Singer Sargent's portrait of Madame X, where he pointed out the scandalous correction made to her strap that caused a stir in its original display.
We encountered William, the ancient Egyptian hippo sculpture that serves as the museum’s mascot, and he regaled me with the tale of Evelyn Nesbit and the infamous murder linked to her supposed nude modeling for a sculpture of Diana, once a weather vane atop Madison Square Garden. Daniel also shared insider tips, such as the best bathrooms (Gallery 207, not the Egyptian Wing as popularly believed) and the quieter 81st street entrance to avoid crowds. My mind raced to absorb all the fascinating knowledge he imparted.
Daniel was informative and passionate during our tour of The Met, yet I couldn't help but notice a subtle change in his demeanor compared to our first meeting. His movements carried a hint of hesitation, and this unease lingered as we paused for drinks afterward, casting a thick silence between us.
"Is everything alright?" I finally asked after several sips of my wine, sensing his discomfort.
He shifted in his seat, avoiding my gaze. "I think going to The Met was a mistake," he admitted quietly.
My heart sank. "Is there anything I can do?" I offered, hoping to ease the tension.
He shook his head, meeting my eyes with a pained expression. "I think maybe now isn't the right time for us," he confessed reluctantly.
I sighed softly. “I understand,” I admitted honestly. I knew that feeling well—wanting something to work out but realizing that timing and circumstances can play a crucial role in relationships.
We rode the train home together in silence, his head resting wearily on my shoulder, the weight of his melancholy palpable.
"I hate that it's not right," he murmured sadly, moments before his stop.
"I do too," I admitted sincerely.
When the train doors opened at Brooklyn Bridge station, he stood but leaned down for a lingering goodbye kiss, a bittersweet moment that stretched into a hopeful pause.
"Let's stay in touch," he said, caught between the closing doors. "Maybe things will be different in the spring when this class is over and we can try this again."
I watched him walk down the platform, his figure growing smaller as my train sped up and away. A sense of melancholy washed over me, mingling with the fleeting hope that maybe, just maybe, our paths would cross again under better circumstances. As the city blurred past the window, I couldn't help but wonder where things would go, and if we were truly meant to be part of each other's stories or just passing characters.
Over the weeks, Daniel would watch my social media stories, commenting often and using them as an opportunity to chat with me, asking how I was doing and sharing inside book-based jokes. I took this as a sign that he might have just been overwhelmed and we might actually connect later in the year when we both had things calm down a bit. He began a new job at a tech company and I settled into my new role and we continued to touch base for several months. Spring grew closer and I grew hopeful given how often I heard from him.
One night, as I laid in the dark in bed unable to sleep, I watched friend’s instagram stories in the hopes they’d take my mind off of my to-do’s long enough for me to fall asleep. Daniel had posted a rare series of stories and I opened them, interested if there’d be an opening for me to be the one to reach out.
It was from a party at his new workplace. He used the pictures to celebrate the moment in his life - a steady job in his new field of study, new colleagues who were fun to spend time with and–I gasped. His girlfriend who had been there for him through the last few months of school.
I reached out to him immediately, sharing the photo of him and his girlfriend. You have a girlfriend?
Yes! He responded nonchalantly. We met a few months ago! It’s been great.
I was taken aback. Had he truly not considered how misleading it was to suggest a possible reconnection while dating someone else? I felt like a fool for waiting.
Oh, he responded when I pointed that out. I didn’t realize that’s what I’d done.
I bit back tears, not wanting to show vulnerability over his insensitivity. You could have told me about her when you reached out.
I wouldn’t have had the courage to tell you, he admitted. I’m sorry.
I chose not to reply, feeling both repulsed and incredulous at his admission. So much for Clark Kent saving the day.
A few years later, as I saw an anniversary post of Daniel and his girlfriend, a photo from a friend’s event he’d attended the night before our date at The Met when he’d met her, everything fell into place. It became clear that I had unwittingly become Daniel’s “the-one-before-the-one.” Just my luck.
When someone reveals who they are, it’s wise to believe them and when it came to Daniel, I did. As wonderful as he was across our dates, something in those weeks together made me question our potential as a match long before I knew he’d met someone else. His melancholic demeanor stood in stark contrast to my bold optimism, and I wondered if our differing outlooks on life could truly harmonize. Compatibility, I realized, extends beyond shared interests—it demands a deeper alignment of dreams and emotional resonance.
Daniel’s efforts to keep in touch while I awaited our promised reconnection left me in a state of uncertainty. I clung to the hope that it was merely a matter of bad timing. However, the notion of “right person, wrong timing” often romanticizes relationships that may not have been meant to be. It’s a way of holding onto hope without a solid foundation. True connections need more than just timing; they demand genuine compatibility and emotional alignment. Daniel’s story taught me valuable lessons about self-awareness and the importance of clarity in relationships.
Ultimately, recognizing when a relationship is not right for us, even when it’s disappointing, is an act of self-respect and maturity. Daniel brought moments of insight and connection into my life, but our paths diverged as we pursued different visions for our futures.