The Coffee Date


Conference days are usually a tremendous waste of time. If you don’t learn anything and you don’t connect with someone you think is valuable then they are usually just hours of preening.
This was particularly true of the conference where I met Sam. Not only did I kill the morning wandering a hotel looking for an interesting conversation. I spent the afternoon, long after I had left the event, thinking about her.
I had a mountain of work to do. I had clients calling for followups. I had both creative and busy work tasks that needed to get done and of course I had to get home.
But my mind wasn’t on any of that. It was on her. It was on the way she walked, the clarity in her eyes. The sense of purpose in her voice. The way she tilted her head when she laughed.
I thought about what she would sound like with my mouth on her neck. What her skin tasted like.That’s why, despite my better judgement, as I sat on the train (nope not the bus) I couldn’t help but pull out my phone.




The popular opinion is that it’s very hard to decipher tone in email and text message conversations. Most of the time that is true, but this benign chit chat gave me a definite feeling. I could feel her warm tone through the words. I didn’t know if I was actually picking up on clues, or if it was just wishful thinking.
I attempted to not seem too desperate by leaving the conversation at “Absolutely” I didn’t want to seem too eager to make plans. If she had observed anything about me, (or done a quick google search) she knew I was married. There is nothing worse than a married man desperate for a single woman’s attention.
So I played it cool.
Until 9:13AM the next morning.




See that? Cool.
Hours passed as I sat in the office. Pecking a word at a time into my newest Powerpoint deck. A word went in, I’d glance at my phone. A bullet point, back to my phone.
Did it light up? Is she cancelling? Did she say something? Finally I couldn’t stand it any more. I left the office and took the walk uptown to the appointed Starbucks. After picking up a simple tall Pike I sat at one of the impossibly small tables and waited. My office in my bag, in an attempt to get some work done. I pulled out my laptop and clicked it open on the table. I stared blankly at the screen that invites you to use the free wifi. I pulled out my phone.


She was a master. Her remarks were just colorful enough to leave me thinking unprofessional thoughts. I tried my best to get some work done for the next hour or so in anticipation of her arrival.
When she finally walked in just before 3:00pm I looked up. Her hair was in its pony tail again, tied straight back. Her makeup was more casual today. Her cheeks, much fuller at a different time of her life, were now highlighted with just a little touch of artificial color. The color highlighted her cheekbones. I watched her scan the room. She wore a navy blue button-down shirt with little white dots. Her shirt was open two or three buttons revealing her upper chest. Her black leather jacket was a wrap over that zipped up her left side. Her jeans were tight. They forced her legs straight when she stood still. She wore black heels and they were high. It was clear she thought about this ensemble. It walked the difficult tightrope of being sexy, feminine and alluring, while also being basically impossible to construe as inappropriate for a business meeting.
“Well done.” I thought to myself, just before she spotted me. She gave me a little wave. I closed my computer and stood. I shook her hand and she pulled me in for the hug women give to professional associates. The one were your heads are unnaturally far apart and only your collarbone areas actually make contact. She smelled amazing.
“Why don’t you sit down. I’ll get you a coffee while you settle in and we can chat,” I said before walking over to the counter. It felt like the final seconds of a double overtime playoff game waiting for that stupid cup of coffee to finally slide across the table.
“Two-Twelve.” The kid behind the counter said. I would have paid two-hundred and twelve to get back to the table. I took a half breath, came around and sat down. Her neckline reminded me of where the windshield meets the hood of a beautiful italian sports car.
“So, we’re here, finally!” I said, probably too enthusiatically.
“We are!” She responded with a big smile. She leaned slightly over the table. her forearms folded one over the the other resting on the table. I sat back on bench, not wanting to invade her space, despite very much wanting to invade her space.
“So, tell me your story. What are you looking for?” I asked. Trying to strike the tone of a friend, instead of an interviewer.
“My story is too long for one coffee meeting.” she began, “I was born and raised here in the New York. I moved away for a lot of stupid reasons, and now I am back.”
“It seems impossible to me that you could have such a long story. You couldn’t be more than what? twenty-eight?” I asked. The question was meant as a compliment. She would later tell me it was callous.
“Ha! Well thank you, but I’m thirty-two.” She replied. At the time, I was 36. The revelation of her age changed her in my eyes. I don’t like girls. I like women. While the difference of twenty-eight to thirty-two is practically nothing, for some reason her being north of the thirty year equator made my attraction to her deeper.
From there she launched into the story of her career. It was clear the when she had left New York, it was for professional reasons but for personal ones. I had guessed a guy. I was kind of right.
“But now, I’m back.” She was bringing her abridged story to a close. “And I’m looking to rebuild my life here. I know my background in art is probably not going to sound directly applicable to sales but…”
“Of course it is.” I interrupted. She paused. She relaxed in her chair a little. She spine softened. She was no longer presenting. She was listening.
“Listen, forget anything else I tell you today if you want, but don’t forget this. Every part of you is important, and even if it isn’t directly expressed the people you work with with feel it. Making art can be essential to making a sale. I don’t mean literally either. I mean using the thing inside you that makes you an artist. Using that thing to make you a better marketer. That’s powerful.” I stopped and sipped my coffee.
She looked me right in the eyes when she said, “Thank You.”
I stared back when I said, “You’re welcome.”
I laid my hands on the table near her arm but not touching her.
“So, it seems to me you need some contacts, some places to reach out.” I said with buoyancy, an attempt to break the logjam.
“Yes!” she exclaimed.
“OK…well I can think of three or four firms I’ve worked with in the past that could potentially take on a freelancer, might be a foot in the door.”
“That would be amazing!”
“Where do you live?”
She paused.
“I just mean are you commutable?”
“Oh, yeah. I’m uptown. Way uptown, but here.”
“Great.” I proceeded to give her the names and numbers of some people that I thought she might legitimately be good for.
I continued, “I’ll email them and introduce you. You follow up with a phone call 24 hours later, OK?”
“That is perfect. Thanks!”
With little else left to say it was time to go, even though I didn’t want to leave.
“OK, well I guess I should head back.” I said over a deep exhale.
“Yeah, me too.”
We gathered our things. I held the door for her.
“Well, I’m headed this way.” I said, pointing south down 8th avenue.
“I’m this way.” She said pointing the opposite direction. I put my hand out to shake again. She took a step forward and threw her arms around me. This wasn’t a corporate hug. I pulled her in. I consumed her scent.
She whispered, “Thank you so much.”
We slowly released our embrace. Even in her heels she was a few inches shorter than me. I held her hand gently. “You’re welcome. Now lets get you some work.”
“OK!” She said with a smile.
I walked downtown, feverishly pecking away the first introductory email. Two tight paragraphs on why Sam was the next freelancer they should take on were flying from my thumb into the screen. Then a text.


I was in trouble, and I knew it.