Find Inspiration, Make a Plan, and Watch it Fail

Sometimes, I revel in ironic shock at the sheer number of things that must converge for a moment to occur -the type of moment that jolts my attention, sends an electric bolt through my mind, stirs my heart, and instantly forms the resolve in my soul: I will find a way meet and get to know her.

The rest is a confluence of meticulous planning, some smoothness, and a serious dose of what could either be called arbitrary luck or the hand of God.

Sometimes, you look across a dimly lit room, lock eyes with a gorgeous woman, and feel butterflies in your stomach. That day, the room was bright, she had just ended a ridiculously long work day, and didn't look back at me. I later found out that she felt sweaty, disgusting, and exhausted. I was nowhere near her radar, though I was aware of her from the moment she stepped into the goodbye party for our mutual friend.

That was the moment I started calculating. I know I've talked about preferences before (here and here), yet it still caught me off guard when I encountered someone who immediately seemed to fit so much of my "type." Every cog in my brain was turning with the express goal of inserting myself into a conversation, finding an appropriate moment and method of introduction, making a point of connection. While the inside of my head churned furiously, I waited patiently. I joined other conversations with friends while very intently paying attention to my peripheral vision. I cannot remember the last time I multitasked so strenuously that my mouth was on autopilot while my brain was in a completely different zone.

She was having a conversation by a table with drinks, so I carefully chose an angled approach to the drink table, ostensibly getting water. Who cares that I was actually thirsty, I was on a mission. I listened hard as I poured water, spilling a little because of my careless attention to the useless task of actually getting liquid in my cup. The moment I turned to add a comment to the conversation, both her body and the conversation took a turn away from me.

Mission failed, for now.

Don't ask how many cups of water I got over the next hour. Sometimes, a move just doesn't work, but for lack of another tactic -and honestly because getting a cup of water and taking a drink is no small comfort in a social setting that I'm feeling lost in -I just kept going back for more water.

One thing I absolutely love about being a man is that when people leave a party, I have and ace in my back pocket; the perfect gentlemanly way of getting into a short conversation with a person of interest is while manscorting her.

It was a short conversation, perhaps about sixteen minutes and forty seven seconds. We walked to the main road where she wanted to get a cab, then spent several minutes failing to find one, to my inner delight. So we contended ourselves with the evolving conversation keeping us company. She had an endearing sarcastic wit to her that could only be described as sassy, and I told her as much. She told me I didn't have to wait, and when I simply stood there with a confident yet semi-puzzled look and said, "I know" to convey that I was merely enjoying the fleeting moment, she insisted by saying "you've been nothing but a gentleman." Of course, as is wont in such picturesque scenarios, that very moment was when no less than four cabs appeared -one from each direction of the intersection -and she was whisked off into the night, leaving me with an extra spring in my step as I walked home.

That was at the end of the evening, and thus the end of this part of the story.

The Chain of Dating

At the beginning of summer, one of my married friends set me up. Not the everyday setup, this one had been in the works for eight months. Yup, that long. It was hard to say no, despite my previous assertions, though mostly because I had practically said yes already several months beforehand. The short version of the story is that the lovely woman and I were alternately too busy or seeing someone else. The sheer persistence of my friend allowed the pairing to come together as the spring semester ended, both for me as a student and her as a teacher. I haven't experienced it often, but on rare occasion someone gets an idea into their head and simply will not let go of it. I have to say, half the time it's flattering and the other half annoying. This time it was more flattering, or maybe that was when it finally worked out after hearing about it every five weeks. 

It was a pleasant first date at a coffee shop, which has quickly become the bread-and-butter of my first date experiences (cue sidebar). Aside from the ease in planning, and the flexibility for length of date depending on how it's going, it requires less thought and investment but can be creative. In short, it's the quickest, simplest, on-the-fly date I can plan with a creative twist if I want to bring board-games or other tabletop activities with locations everywhere. I've been known to shoehorn the coffee first date into an impromptu park walk or parlay into another date-like activity when it was going very well, and finish my drink faster to end it within an hour when it's not. 

Rant aside, I enjoyed the date. I found her bright, opinionated, accepting, passionate about her career, and we connected in our mutual interest and joy in working with children. It was, however, short lived. One and done, as she didn't see our personalities meshing. I was impressed and found myself thinking that she's fantastic, despite my limited experience with her. I had hoped to get to know her better. Oh well. 

Then the chain began. She set me up with a friend of hers, and I do sincerely believe that someone I've been on a date with knows me better than a Shadchan would, at least in the realm of experiencing me. Since I'm not much for categories I thought I'd give it a whirl. Another coffee date. Another one and done. She set me up with a friend of hers too. It all began to feel a bit like I was getting passed around a group of friends -all of whom let me down easy (read: guiltily -though it made me curious as to why is it that these wonderful women felt so bad about not being interested?), said I'm a great guy, and set me up with a friend in turn. At least the last one had a bit more substance -intellectual conversations over art, talk about emotions and matters of the heart, getting deeper into our personal stories -the kind that are milestones and shape who we are. 

As an aside, I joked with my sister that I was being handed off. Then she told me that she recently did the same thing with a number of men she'd dated over the summer as well! Of course I heard stories and connections that were made about the personalities, interests, and wants of these men and what inspired the idea. It was eye opening to see that from the other side. 

Ultimately, the dating chain ended. As it turns out, I still prefer the flexible, potentially spontaneous, straightforward coffee first date. I also had a light bulb moment after my summer dating stint. Dating is a huge pain, right up until the moment you find someone you like (and who likes you back). Then it is the simple thrilling joy of discovering that person (and, incidentally yourself).

But that's another story for another time. Soon.