THE DATING EXPERIMENT

The names, dates (pun intended), and women in this experiment have not been changed. I figured, why bother?

The idea was to gain some confidence, not watch my date pour 15 beers down her throat. But life’s full of sweet little surprises, isn’t it?

In his New York Times bestseller, The Four-Hour Work Week, Timothy Ferriss challenges the reader with a task at the conclusion of each chapter. One is to ask someone out (that you do not know) every day for a week. I decided to take this challenge, and being that I often take things to an extreme, I did it for three weeks: 21 days, 21 girls, 21 asks.

How does a guy go about asking a different girl out every day? I decided I needed to be organized, I needed to make sure I had a plan. I live downtown in a medium-sized town, so I have access, theoretically, to lots of single girls on a given day. But placing myself in a situation where I could ask someone out every day, that I decided, may be tricky. I also have children, a job, and responsibilities, so I had to frame the experiment within that world.

With little to go on, I decided to start on a Monday morning – that’s where all great starts “start”, right? Right. I mean, whenever you talk to someone who’s starting fresh, they invariably say “starting Monday.” For example, “Starting Monday, no more armed robberies for me. I’m done!” Feeling a little bit like I was embarking on a crime spree, I got a good night’s rest on Sunday, determined to be fresh on Monday.

Day One
My office is just three blocks from the main street of downtown. The post office, library, retail stores, restaurants, bars, and coffee shops are all within walking distance. I decided I would take care of the “ask” at lunch time. I walked down to my bank, figuring a single lady would sort of appear.

I quickly realized that this experiment is not “whack-a-mole” – it’s not single women popping their heads up as I stroll down the street, me with a mallet labeled “Do you want to go out?” stamped on the end. That sounds so easy. But no.

I walked into my bank and decided I’d ask the teller out on a date. I’d noticed her weeks before and made small talk, but nothing else. What do you say, “Yes, I’d like $45 from checking and your phone number?” It seems so cheesey. But, I think cheesey is going to be unavoidable.

She’s an attractive girl, but not intimidatingly so. There’s no ring on her finger, and she’s nice to me. Of course, that’s her job, but still. I saddled up to her window and froze. Not only can I not ask her out, I can’t even find the words to tell her what financial transaction I want to make. I’m like a member of the Apple Dumpling Gang. Finally, with some hand-holding from her, I got my banking done, looked her right in the eyes – and said “Thanks”. I chickened out.

I sped out of the bank, a miserable failure. The girl was cute, and I should have asked her out, whether I was doing this experiment or not. But I choked. I had about 30 minutes left before I needed to get back to my office. The chances of meeting anyone in my office were slim. I had to find a girl.

I walked to the coffee shop and got my usual – chai tea. “Oh, I love it with cinammon,” came from my right. The word cinammon was still lingering in the air as I turned to see the source of the comment. She was casually leaning on the back of the couch, her hands clenched around her warm cup of java, a scarf twisting its way around her neck, falling to her chest and down to her waste. She had style. And she wasn’t afraid to speak up. I liked it. As for her appearance – she was almost elegant. Not truly elegant, because let’s face it, how many elegant people are there in the world? Maybe two dozen? What were the chances that I’d stumbled across one at the Espresso Bay coffee shop? It was a billion to one.

“I like vanilla, but I might be persuaded to have them sprinkle some cinammon in there, ” I shot back at her. “But how am I to know you have good taste?”

Laughter, a flip of the scarf, and a sideways smile. Golden stuff.

“I guess you’ll have to trust me,” she said, turning to look at nothing in particular in the direction of the fireplace.

After my drink arrived (with cinammon), I sipped it, performed the requisite – and quite predictable – “yummm” and glanced toward the scarf girl. I walked over and told her thanks. I proceeded to roll out some of my best at flirting.

“Do you have a job, or do you just sit in the coffee shop telling people how to take their tea?”

She didn’t immediately laugh, which I liked. She smiled, and spat out: “I just love cinammon, and would hate to see you miss out on it.” As I smiled at her response, I couldn’t see if she had a ring on because she was wearing gloves. It was like two degrees outside. I decided to wade right in.

“I have to go back to my office, but would you like to loiter in the coffee shop with me sometime, and we can both tell people how to get their drinks?”

There it was, one ask down. She tossed her scarf to the side to reveal a bag, scribbled something, and slipped a piece of paper in my hand. I turned, not lingering (remembering that asking a girl out is like being a Marine going into hostile territory under fire to pick up a fallen buddy – when you get the number, get out!) and thanked her again, rising my warm cup of tea to her. Thanks, scarf girl.

Next: Part Two >