Coffee with a Stranger #1 (Part I) - Coffee with Self-Doubt

My first Coffee with a Stranger was scheduled on a Tuesday afternoon at Cafe Madrid in downtown Oakland. I had no idea what to expect. Not only had I never been to Cafe Madrid, but this particular stranger was a somewhat guarded and secretive individual in our pre-meeting emails. It was made very clear that privacy was of the utmost importance to this person, what with Google's prying eyes tracing our every step like a bloodhound following a potent scent with wild eyes, lolling tongue, and bristled fur. Or at least that's the way I picture it. I am, after all, a guy who refuses to post anything personal on a certain social networking site. Instead my page features the mildly inappropriate exploits of a stuffed animal. Seriously. I even spent time posing this stuffed animal in scandalous positions for the eye of my camera.

So, yes, I was going into this meeting with very little prior knowledge of this stranger. I wasn't even sure of gender, as his or her emails cheerfully signed off only with a pair of initials. I did know that this individual found my ad on Craigslist while searching for jogging partners. There was also mention of always being interested in writing, but being "too chickenshit" to take a class or pursue the idea further. Some other tidbits shared were the fact that he or she was unemployed, looking for temp work, and that some friends had had "scary experiences" with online dating.

Armed with these details, a tape recorder, a pencil, and a notebook, I head to Cafe Madrid. It was a dreary, overcast winter afternoon and downtown Oakland was, as per usual, somewhat deserted. As I approached the cafe, a woman coming from the opposite direction was also heading for the same cafe.

"Aha!" I thought to myself, mentally stabbing the air with my finger. "Maybe she's the one behind those cheerful initials!"

This woman was short, likely in her mid-thirties, and had long, wavy brown hair that reached down to her shoulders. She carried a squat, brown bag over her shoulders and a massive book in her hands. She looked up at me, looked as if she might smile or say something, then quickly looked back down and hurried into the cafe.

I was crushed! I was sure this was my mysterious first stranger and that she had taken one look at me and freaked out. As per our agreement via email, I was wearing my brand new, Flashback Friday Toronto Blue Jays hat (an incredible Christmas gift from my sister and the most noticeable piece of clothing that I own), so there was no mistaking me. After all, other than Raiders' hats, jackets, tattoos, eye patches, and head-to-foot costumes, there's not much sports paraphernalia being worn in downtown Oakland.

I followed this woman into the coffee shop. I may even have held the door open for her. My gut said that she was the one. I stood behind her in line, listened as she ordered a cup of tea, and watched as she fumbled between her squat purse, her Biblically sized book, and her wallet. I was even extra nice to her at the milk and sugar table. "Take your time," I assured her, my small coffee in my hand, as she rushed and fumbled some more with bags and books while pouring milk and sugar into her tea. I got a wane smile for that little effort. I realize now that maybe, just maybe, I might have been freaking her out with my expectant stares and over-politeness. But I was just trying to be nice! As I topped my coffee with milk and sugar, I watched disappointedly as she shuffled off to a far corner of the cafe. And by far corner, I mean tremendously far, as Cafe Madrid is really quite spacious despite a rather small clientele.

I decided I too should take a seat. I sat near the front door by a large window that looked out onto the street. And, no, don't worry, I didn't sit uncomfortably close to that woman who I suspected was Stranger #1, so I could continue to stare at her from beneath the brim of my brand new Blue Jays' hat. That would be odd. We were, in actuality, almost at exact opposite sides of the cafe, although I still had a clear view of her. She was busy sipping her tea and reading her Biblically sized text. I wondered what that big book could be. Harry Potter number four, five, or six? An Avatar-esque sci-fi/fantasy novel? Foucault's History of Madness? The Bible?

This is when the self-doubt really started to kick in. Was it ridiculous to think that this project could actually work? I mean, really, who in their right mind would agree to meet me at a coffee shop, so I could record and write about an unscripted, shoot-the-shit session between the two of us? Did this woman across the coffee shop, quietly reading, sipping her tea, and fiddling with her hair, see something creepy about me that I'd never noticed before? Was I too young? Too old? Overdressed for the occasion? Underdressed? Did I have spinach stuck in my teeth or Worchester sauce splattered across my cheek? Or maybe I just looked a wee bit ridiculous in my brand spanking new Toronto Blue Jays hat? Maybe not as ridiculous as this guy to the left, but close?

Soon 5, 10, 15, and finally 20 minutes passed as I nursed my small coffee before a table laid out with my tape recorder, pencil, and notebook. Part of me wanted to give up on this project entirely and head home with my tail between my legs. That is, of course, until I focused my attention once again back to that woman with the Biblically sized text. She had to be the one! I had to confront her! Looking back, it's somewhat odd that I didn't first consider that maybe I'd just been stood up or forgotten. I really had it in my head that that unsuspecting woman was my stranger, but for some reason she'd taken one look at me and decided against our meeting. It was then that I decided to approach her. To walk across that cavernous coffee shop and ask this woman if she was here to meet a stranger for a cup of coffee. To confront her. To figure this situation out. Why not give it a shot? Nothing ventured, nothing gained!

That, apparently, is what self-doubt can do to a guy trying to kick-start a writing project involving anonymous strangers found over the internet. I battered my doubts from the internal (me) to the external (unsuspecting woman) like a birdie hit between two hard-smacking, trash-talking badminton players.

Before I could initiate what was bound to be a somewhat awkward and accusatory conversation, luckily another woman came rushing into the coffee shop. Her hair wet and recently brushed, she took a quick look around before making a beeline for a certain brand spanking new Toronto Blue Jays hat. This little project of mine still had some life!