We are enjoying every bite of our delicious meal at a neighborhood cafĂ©, peering into each other’s eyes, holding hands, and it feels great. The beginning of the end of summer cools the energy and we cherish a few fleeting moments. We look great with each other, we have so much in common, the sex is juicy and tender, and we’ll probably never see each other again after one last night. I like Rachel and I’m hoping she won’t feel hurt after we are over. I’m also hoping that she doesn’t see pity in my eyes while I’m debating with myself whether she has a right to feel misled. “I told her right upfront that I was not looking for anything serious. Her eyes were hurting, but she played it cool.” The circle of corruption continued…

I met Rachel two months earlier at CVS. I had just moved into my new bachelor-ready digs and was enjoying a lazy Monday morning discovering the neighborhood and buying the men’s basics: shaving cream, hair gel, and condoms. She saw me looking at hair gels and walked by, then came back into my isle, looking lost and confused. She was very tall with a smoking body, but at that moment she seemed to be the most vulnerable little girl on the island. The predator blood rushed in and I walked toward her, waiting for eye contact. She looked up at me with a virgin anxiety; her eyes spoke: “Talk to me! I spent another lousy weekend alone! I am amazing and I am yearning to be romanced, courted, charmed by my equal who protects and takes care of me, who is fun and outrageous, who loves children and dogs, and is willing to go all the way… I am so ready for such a man!...” I should have passed by, she did not look like a “player,” so it was not fair to her, but my empathy cheated on me with my compassion a long, long time ago. So, I said, “Hi.”

I don’t know why I slept with her on our first date. Was Rachel so good that I wanted to accelerate the end of our relationship, afraid of where it might go? It was the same script: trendy meal, drinks and little dancing at some posh club, walking to her place, first kiss in the middle of the street, second kiss at her doorstep. I am caressing her left palm and she is moving in closer craving for another kiss, her deep grey eyes exuding fear overpowered by pain; they speak again, “I must not invite him up. I like everything about him and want to take my time. I want to have many more evenings like today!” I take a brief moment to think, I want so much to just say, “Good bye,” and to extend the levity of courtship… but I give her my softest kiss yet and her building’s concierge welcomes me into the family…

The waves of my daily depression come ashore unexpectedly. Lilly and I are having wine and chocolate on my rooftop. Her glowingly young skin, assertive boobs, and promising lips make her story about Dali’s museum in Barcelona so much better, but I am empty of desires. I don’t want her to leave either; I am just dreading being alone tonight. It is not a night for a friend, it is one for a woman, and I don’t have energy to call a hooker… so Lilly will do for another couple hours before the revolver of another nightly coma gets closer to my temple. I am enjoying her blue eyes and sparkling teeth while contemplating why I even bother with “dates” instead of engaging an hourly professional. As Lilly stops, I am asking her about Madrid, sparing another few minutes for my thoughts… I like to cuddle, which would not be the same with a call girl… I only like first dates and veni/vidi/vici later I don’t want to see those women again… I like the game but don’t care about the outcome… Lilly stops, and I still don’t have the answer.

Groomed by Dumas and refined by Salinger, I was an absolute romantic in my early teens. My vessel has sailed very far from that home: with every month of dating, with every relationship, I am gaining finesse but losing the desire to use it for more than the first few hours. Where is my Helen Hunt, who would make me wanting to be a better man? Do I really have to look in Brooklyn for her? 

Jasmine, a waitress in my favorite hip-hop joint, channels me another warm wave with her big green eyes. This time I am sandwiched between two college girls and feel awkward promising anything back. As the front girl suddenly turns around and pulls up my sweaty t-shirt, I look apologetically at Jasmine, semi-hopeful that she will see my well-toned body… she is no longer there. I straddle my two new friends with my long arms and we go for another hour before they become inappropriately wasted and leave the club holding each other. I make my way to Jasmine contemplating if it is mathematically possible to take her straight to my place from here. “Hi,” I say. “Another waiter told me your name is Jasmine. You look amazing, out of this place.” She smiles and waits. “I am sorry for my inappropriate dancing, too many tequila shots. Can I buy you a drink?” I continue. “It is 3:30 and I can’t drink until we close at 4,” she replies. Her smile is so sincere, too sincere, and I suddenly change my mind, at least for tonight. “That is a pity. I will be back. Please don’t quit till next week.”

Cabbing home, I can’t help but feel that I may be on to something. Maybe the key to the proper Manhattan courtship is not to court as frequently—depth vs. breadth so to speak. Tonight, I am sleeping alone, and it is my contribution to the island’s humanity… baby steps.

Holden Wilde is a first time author who lives in New York, NY.