Date One.

There was something going on with my eye. I don’t know if I got Oil of Olay in it or what. But the right one was totally red and sickly looking. This is the kind of thing that, naturally, only happens when you have a job interview, when you’re at an event where you’ll have your picture taken often – such as a wedding, or if you’re going on a first date.

Which is what I was doing today.

I didn’t have much time to dwell on this, as the place my date had chosen to meet was almost 45 minutes away from my apartment. I pulled together one of the outfits Sheri had created for me. She was on vacation so I couldn’t get her final input – but maybe that was for the best, because then I’d have to admit to her I’d forgotten to get a manicure.

As I rode downtown, I worried I wouldn’t remember how to act on a date. After all, it had been almost two years since I’d been on one. What if I couldn’t think of anything to say? What if I choked on my drink and it came out my nose? Or went to the bathroom and returned with toilet paper stuck to my shoe?

But when I emerged from the subway, I was starting to feel more hopeful. My eye had cleared up a bit, the early evening sun was shining merrily and my hair looked fantastic. I started on the long walk West to meet my date. A young Union Square bohemian sidled up to me. “I like your necklace,” he said in an alluring Italian accent.

“Thank you,” I said and flipped my hair. I began to walk with more confidence.

He was waiting outside. And he looked way cuter in person. I could feel my excitement building. He lived in Williamsburg so was wearing the mandated uniform of skinny jeans and a quirky sweater.

“Hi!” I said with a smile and a wave. “I’m so sorry I’m late. I hope you got my text. I came from the 4 Line and I underestimated the walk time.”

“It’s fine,” he said with a curt nod. Indicating clearly it wasn’t. I glanced at my phone as we entered into the basement bar. We were to meet at 6 o’clock. It was 6:07.

We settled into a table where I ordered a Pilsner and he ordered a specialty cocktail.

“So,” I said. “You mentioned you had a teleconference today? How did that go?”

“It wasn’t a teleconference,” he corrected. “It was a one on one remote interaction with one of my global clients.”


“You know, you didn’t mention what you do in your profile? I know you said you were self-employed – ”

He cut me off. “I teach people how to overcome their deepest fears.”

“I see. How did you get involved with that?”

“My own crippling social anxiety.”


Look, I know I write an incredibly personal blog every week that strangers read, so I shouldn’t judge. But even I draw the line at being too intense on first dates. Especially in the first five minutes. My friend Shannon always tells me, “Hide the crazy, Tracey. In the beginning, hide the crazy.” This philosophy had worked well for her as she married an awesome guy who now responds to her theatrics with a good-natured laugh and an offer of a glass of wine.

He was still talking.

“There was a point in my life where I would get on a bus and just ride it around and around because I was too intimidated to request a stop.”

I honestly had no idea what to say to that.

“So what do you do?” he asked, as he swirled his straw in his bourbon-based drink.

I hate this question. Now, I love my job. I work with incredibly intelligent and creative people who make me laugh everyday. It is a stress-free enough environment that I can leave there with the energy to work on outside projects and since it’s a start-up, we have a ping-pong table. But I am also aware that there is a preconceived notion that if you are an assistant, especially at my age, then you are an idiot. I know, objectively, this is not true. I have a lot of friends who are assistants and they are all bright, diligent and master multi-taskers. We are the people who run the lives of the people who run companies.

But my own insecurities always take over. So then, in an effort to make myself seem like I have more going on in my life than what they probably think is just arranging other people’s travel and setting up various meetings, I’ll start talking about my writing. Which never fails to come across as pompous. That’s tricky thing about first dates. You have to talk about yourself, it’s a given, and that can be really tough to do without sounding like a total jackass. Especially if you’re talking about something as ‘artsy’ as writing.

“What do you write?” he asked.

“I wrote a novel a while back that I’m going to publish in the Spring. You know, just self-publish on Amazon or something. Just to get it off my plate and out of my head.”

God, I sounded so pretentious.

“Well.” He sat back and folded his arms across his chest. “I’ve published five novels.”

“Oh,” I said, feeling much less remarkable.

“Let me tell you something” His enthusiasm caused him to lean forward. “There is a book out there called ‘A.P.E. Author, Publisher, Entrepreneur.’ It taught me everything I needed to know about becoming a successful author.”

“Thank you,” I said sincerely. “That is really helpful.”

“A.P.E.,” he said again. He pulled out his phone. “I’ll text it to you so you won’t forget.”

I was pretty sure I wouldn’t forget such a simple acronym but whatever. He was just being helpful.

Our conversation went on and I noticed he was the kind of person who often closed his eyes with reverence when he spoke, to better hear the sound of his voice.

“I lived in a car for eighteen months.” He opened his eyes and pointed directly at me. “BY CHOICE. I looked around and thought to myself – what do I really need? Some clothes, my laptop. My juggling equipment. That’s it.”

As I tried to hide my bemused expression, I sat back and thought to myself, “This is a perfect first date.” I didn’t feel any pressure at all to impress him so I was free to just relax. In fact, I could use this opportunity to practice my dating skills. I asked a lot of insightful questions, I listened intently, I laughed in all the right places, I sipped my drink demurely. I actually thought a lot of what he said was quite interesting and funny. And he was obviously very smart. These were all the reasons I’d messaged him in the first place.

But that didn’t mean I wanted to see him again.

As we exited the bar, neither of us even pretended there would be a second date. I thanked him again for the drink and we both said it was nice to meet each other. And then we went our separate ways.

“Omg,” I texted my friend Bree. “It’s 7:15pm and I’m already on my way home!”

She wrote back, “I’m sorry, babe :(”

“No, it’s fine.”

And it really was. I wasn’t upset at all. In fact, I felt great. I’d been proud of the way I had handled the date. I’d had one drink, asked good questions and been funny and receptive. Perhaps I really could do this dating thing.

I put on a little Travis Tritt to add a spring to my step as I walked the many, many avenues to my subway. And as he sang, “It’s a great day to be alive!” I thought, “Indeed it is, Travis. Indeed, it is.”


13 thoughts on “Date One.”

  1. Well, I’m sorry your first date was…a dud? with a putz? blog fodder?…I’ll quit trying cuz (does that peeve you?) I realize that’s not the point – yay for your perspective! Yay for your attitude! Yay for your entertaining blog!

  2. this date is hysterical. seriously fantastic. five books, social anxiety. APE lived in a freaking car by choice. I love this guy, what an ass. only thing that would have made it better, a sweater with puffy paint on it. brilliant date!!

  3. Tracey, Meg and Kim have recommended your blog so highly I had to check it out. You are, as I always assumed, an engaging writer and I look forward to more. Especially whenever you get around to telling stories about days of New Years Eve pasts….

    1. Omg Darren, that is so funny you say that because I actually HAVE wondered how I could incorporate that night into the blog!! Lol! Thank you so much for checking in and for the kind words. I’m really pleased to hear you like it 🙂

  4. Hi Tracey, Well, they say you have to kiss a lot of frogs before you get a prince, so: Frogs: 1, Princes: 0.
    Your attitude of controlled humor is perfect…fun even without connection.

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