The continuing saga of a man who asks out a different girl every day for three weeks. On purpose.
She looked like the kind of girl who would stand in line for concert tickets. The kind of girl who sent cards to her friends on their birthdays. It wasn’t enough that she was pretty, she had to be patient and thoughtful too.
I was in the library, piggybacking their wi-fi signal. She was in fiction, somewhere between Jack Kerouac and Stephen King. This was Day Four of The Dating Experiment. I was starting to reach a comfort zone. Not that I was comfortable asking the girls out, it was more like I was getting more acting a fool. That’s really what we men are doing, putting ourselves out there. It isn’t fair, of course, but then again, women endure childbirth. The “long walk” and “the ask” are the male equivalent of labor pains. I’ll take that trade.
The previous two days I had played it safe: a smiling, round faced girl behind the counter of the bakery as I shopped for a cake for my daughter’s birthday; a blonde in tight jeans at lunch who looked a lot like a friend I had went to elementary school with. That was my opener to her, and 10 minutes later, as we ate our salads together, I asked her for her number. She actually blushed. Red and everything. “This never happens to me,” she said. No kidding, I thought, this doesn’t really happen to anyone.
Neither of the women from Day Two or Three were girls I would normally have asked. For the record, the Bakery Girl said yes. We laughed a lot as I wisecracked about donuts:
“What did they do with all the donut holes before they decided to start selling them?” and “Have you noticed that donuts are a lot like your customers: some are fresh, some are stale, some are crummy.”
Yes, really. I said those things. And she didn’t throw a fritter at me.
But this was about the Library Girl. I had to get myself into her space somehow without seeming like a freak. While I was figuring that out in my mind, another thought was also floating in the back of my head: she would almost certainly turn me down. I was three-for-three. Like Pete Rose or Joe DiMaggio, I was on a streak. But eventually “Charlie Hustle” struck out, and even ”Joltin’ Joe” was dumped by Marilyn Monroe.
Fumbling my way down the same aisle and pretending to look for a book seemed a lame approach. While I was congratulating myself on the obviousness of that decision, a woman approached and started chatting with my target. Library Girl had bumped into a friend, and the woman was someone I’d met once. But I couldn’t remember her name. Luckily, she remembered me, and after I stared at her for several seconds, she did the smile and wave, along with a library whisper: “Hi!”
I sprang up and settled in next to the two girls, certain that my “friend” would introduce me to Library Girl. Bless her heart, she did. Library Girl had a name, which I’m sure was embossed on her very own Library Card: Allison. Nice.
I made a comment about her watch. That sent her into a story about where she bought it and who was with her, etc. Which reminded me that never in my life has a guy friend complimented me on a piece of my jewelry, to which I’ve responded by telling a detailed story. “Oh yes, I found this pinky ring on a guys’ weekend in Chicago with Dale. It was in this tiny little shop off 144th street. It was such a steal!” And so on.
A few minutes later, Mutual Friend left, and I retreated back to my laptop. I figured Library Girl would be browsing the stacks a while longer. Turns out she’s quite a page turner, because she spent several minutes in the next two aisles, working herself up to James Joyce, I’m sure. (Mental note: don’t go grocery shopping with Library Girl)
By this time she was only a few steps from me, and I made a production out of packing my laptop in my bag. I stopped to say goodbye, and got the ask in.
“I wish I could grab a coffee now, but I have to go to a meeting right now, would you like to chat over coffee sometime?”
“Um, yeah.”
What? (I almost said that out loud).
Honestly surprised that she agreed, I was sloppy for a second or two, forgetting what to do next. It’s important, by the way, to have a business card, or a piece of paper, and a pen (especially a pen) at the ready. They really should make a pen holster. The girl says “yes” and then BANG! like Redford in the Bolivian scene in Butch Cassidy and the Sundance Kid, you have a pen in her hand. But I’m not Redford. I’m not even Strother Martin (“That’s what happens when you ask strangers out on dates: you get colorful…”).
I got the number, she seemed pleased that I asked. I’m four-for-four. Is this possible? Has someone conspired to make me feel good about myself or am I stupid-wild-ass-lucky? I felt like the man who was putting a sandbox in his backyard and struck oil. Except a girl’s number is harder to get than a pocket of petroleum beneath the earth.
This can’t continue. Something has to give, doesn’t it? I don’t even have a library card.
Next: Part III (coming soon) …
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 >