Adventures in Dating: First Date, The Philosopher

April 9, 2015: Harlem, NYC

Hello! I had to pause writing a bit so I could focus on some career stuff this past month, trying to help future Megan land a job once the sabbatical is over.  And we were just finally getting to the good stuff!

See, at the onset of my NYC Tinder stint, my friend Chellie encouraged: “You don’t even need to meet anyone, you can just chat with interesting people and leave it at that.”

This was appealing, since it seemed less awkward and far easier than sitting down for a drink with a perfect stranger.  But, as I’m trying to remind myself throughout this season, I didn’t leave a perfectly good job to take the easy route.  I left to push myself and grow.  So, there would be no other way forward than to actually go on a date.

Once this was decided, I set my sights on The Philosopher.  He chatted with me right after I joined Tinder and I quickly learned he teaches special education history and philosophy. In a word, he was unthreatening. If I was going to make myself go on a date with a stranger, this was the guy.

 We chatted a bit before I cut to the chase, eager to get this experiment out of the way:  “You seem pretty cool and normal, so if you’re on Spring Break right now, I think it would be fun to grab coffee or something super casual.”

And I would have been nervous to put myself out there except that I truly had nothing to lose, and I just wanted to get a date over with, especially with someone so seemingly safe.  Impatience and opportunism can be a wonder for facing your fears.

And lucky for me, The Philosopher was on board.  And so it was, that I had my first date post-long-term relationship with a stranger at Harlem’s Double Dutch Coffee.

And you know what? It was decidedly not horrible.  He was a nice guy. Smart. Funny. Interesting. Cuter than I expected. (I hoped we’d get on the level where I could help him revise his profile since his myriad bathroom selfies didn’t do him justice.)

We talked about the challenging life of a teacher, laughed about dumb parking moves that result in tickets and/or vehicle impounds and relived some of the best Toby-Michael Scott moments from The Office. (“I hate…so much…of who you choose to be…..”)

But the highlight of the afternoon was simply spending dedicated time getting to know another human, peering briefly inside the mind of someone who sees life at a deeper level. I won’t forget what he said when I shared why I took time off to reflect on what I’ve done and contemplate how I might move forward:  “I think it’s a fair question to ask, really: is what I do good enough to actually be done in the world?”  There are few people I know who would phrase it just so, but as of today, my new friend is one of them.

A couple hours in, we both needed to get on with our days, and I had no clue how to conclude.  We gave a general, “great to meet you, thanks for meeting up!” and went on our way.   I trotted back to the apartment just so pleased by the whole thing.  For once, my bold half battled the risk-averse half and actually won.   And to top things off, perhaps an hour later –

And never mind that he doesn’t spell hanging with two ‘g’s, I WIN!!!  All of a sudden the fear and nervousness are eclipsed by excitement and I can’t help but think: wow, if this is modern dating, it’s so FUN!  And Tinder, people must have been wrong about you, you are GREAT! (Oh emotions, how quickly you swing. You, in your wisdom, probably know this won’t last, but I was still an online dating ingenue.)

Though the date seemed positive, though the follow-up was almost instantaneous, I didn’t actually see The Philosopher again.  (Except for a chance encounter a few weeks later, but that gets ahead of things.)

And here’s what seems interesting about Tinder, dating in general, and perhaps life overall:  right about the time I think I have things relatively figured out, writing my plans in pen vs. pencil, imagining sunny afternoon dates reading Frankl and Rousseau and contemplating our human existence…it seems like right about then is when the plot twists seem to happen.  In retrospect, I was both disappointed and intrigued by the change of direction with The Philosopher – the disappointment speaks for itself but I couldn’t help but be intrigued by what could happen next, now that I’d at least been just a little braver than the day prior.

So for now, let’s keep moving.  Because once I’d left my comfort zone long enough to meet someone new, I figured I’d better keep at it while I still had the nerve…


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