When I met the man it was the dead of summer in Brooklyn. I was sitting at Sycamore. The heat from outside oozed in behind each new person that stepped into the bar. I sat anxiously on a stool near the front, waiting. I was waiting on a first date. I was waiting on a blind date. Ok, I was waiting on an online date. It wasn’t the first online date I had been on, but it was the first one I’d been on with high hopes. Prior to meeting the man, I had refused to have too many back and forth emails before meeting up with someone from Okcupid; however, due to circumstances and the man’s personality an email exchange had happened before this date. We had written back and forth for at least a week and a half, and I had already become somewhat smitten.

We’d decided to meet up in my neighborhood for a early summer, late afternoon drink. Nervously I’d prepared for the date. I’d even bought a new shirt to wear, fairly unlike me! Now you may have an idea of the moral of this story from my post title, but this is not a story of taking risks in one’s dating life. This is a story of taking risks for your creativity.

On that hot afternoon, while I sat there waiting, I also nervously clung to a manila envelope. Inside was a portrait of a small chihuahua wearing a red velvet crown. The drawing came to be because of a comment in one of the man’s emails from the previous week. After our first few emails, he had checked out my shop and commented, nonchalantly and most likely hypothetically, that a dog portrait would be the perfect birthday gift for a friend. Of course, I knew this was hypothetical. Perhaps if we went out on our date and ended up having a second or third, then the real request for that portrait would happen. But as if taking on a dare, I decided to take the risk of going on this first date with all my cards on the table. If he liked me, the quirk of bringing a pet portrait along would only be charming, right? Or perhaps a little crazy-seeming and much, but it is true to me. Not to mention drawing a new dog makes me happy.


On the night before our date, I sent him a quick message. It read something along the lines of, “hey, if you want that portrait, send me pic of the dog. If this okcupid thing doesn’t end up working out past tomorrow, at least you’ll have a cool portrait out of it all.” He responded quickly with a “hot pic” of said dog and a special request, “His name is Prince Vega. I think it’d be cute if you could draw him wearing a crown….” For a split second I panicked. What if I couldn’t really draw a good portrait of a chihuahua with a crown on. This was quite an unusual request. The man in his emails was pretty funny and quirky and let’s face it, this request just added to my excitement.

I know that many people would have left his suggestion at just that, but I took a risk. Was it hard? Definitely. Not just making it, but showing up with it was as well. When he walked in I nervously handed it over, without even giving him much of a chance to adjust his eyes to the darkness of being inside. That was certainly an awkward exchange. But out of it came one of my favorite dog portraits, a great first date story, and my wonderful relationship with a guy as quirky and open as I am.

Creative Impulse Series

This post is part of my Chasing the Creative Impulse Series, which explores techniques for sustaining creativity in a busy life. I believe that the habit of creativity comes from practice and not just from a compulsive feeling to create. This series outlines ways that I’ve maintained a creative life.

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