Adventures in Dating: The Real Estate Broker

I thought this was an awkward kiss story.  Turns out it’s more about risk and Jack Kerouac.

April 5-9, 2015: Harlem, NY

The Real Estate Broker reads about my hiatus from corporate life and quickly wins me over:

I’ve never read anything by Kerouac –  I know he was a bit of a free spirit who wrote On the Road, and that’s all I’ve got. But the authorial allusion and his use of “renounce” is really attractive.  This might seem like a low bar, but remember, it’s Tinder.  Comments this intelligent are disproportionately impressive.

He asks what I’m up to with “New York and time at my fingertips” so I invite him to grab a beer with a few friends. We settle instead for a date two days later.

I met the Philosopher in the afternoon and went out with Aaron and Caty for dinner that night. Dinner had been planned for weeks –  tasting menu at a restaurant by one of the former Top Chefs.  So my food-nerd hosts were thrilled. And we’re working through the fifth or sixth course, chatting like normal, but then there was one of those moments.  You know, when your emotions turn on a dime and you go from thinking “I guess I like ahi tuna after all” to “holy sh!t, I don’t know where my life is headed and I’m terrified.”

So after a great date in the afternoon, and a wonderful dinner, the uncertainty of this season has taken an unexpected toll that night and I’m suddenly not feeling up to this next date.

Because to be on a first date when you’re sorting out your emotions seems like an incredibly odd thing, sitting with someone you’ve never met and trying to neatly sum up your present existence.  What do you say, what do you leave out, to be genuine, but not alarming?  “I’m trying this sabbatical thing, which has been a good experience so far, except for occasional moments when people ask me where I want to be in six months and once I remember that I don’t know, I have an emotional freakout…”

So when I meet The Broker, I opt for a bit of a song and dance, and he doesn’t press too much for depth and disclosure so it’s easy to get by.  We keep things light: music taste, work, his old soul nature, and of course, the glory days of Nickelodeon. (All That, anyone?)  He orders a second and third drink so I had to assume things are going fine, and I’m enjoying myself inasmuch as it’s generally fun to get to know someone brand new. But no real sparks.

It’s 1 am already and I’m more than ready to call it a night. We stroll up the block until it’s time to diverge, me heading across the street to my apartment, him North to the subway.  I wrap things up as best I know how: “thanks for coming out; maybe I’ll see you on Tinder sometime” – then I commit my rookie mistake: a hug.  Wrong decision.  Because once we hug, he keeps me there in a prolonged embrace, and now I’m stuck. He’s barely inched past “stranger” to “very very casual acquaintance” and there I am, 50 yards from my apartment, and five inches away from confused puppy dog eyes that implore, “but don’t you know what happens now?”

He persists and leans closer, and I’m awash with confusion and incredulity.  We had just an okay time, so where is this coming from? Is this how it goes?  I considered giving in, but this wasn’t the date, this wasn’t the moment.  I didn’t feel any real danger, but I very much wanted to get home lips unscathed. Not having remotely considered this contingency whatsoever, I was left to improvise:

“it was good to meet you, but I’ve gotta get going…”

He only smiles, and as I subtly juke left to break the embrace, he moves with me and is still pretty much thisclose.

So I do a micro-calculation of what Courtney would do.  Courtney’s a former coworker who taught me how powerful it can be to simply tell the truth.  So, I summon my pseudo-assertiveness to give it one more go:

“Hey – it’s been great to meet you, but… I’m not going to kiss you.  And I’m sure you’re going to respect that because you seem like you’re a good guy. So I’m going to get going, and thanks again for coming out.”

And with an obliging smile, he releases with a look of, I think you’re missing out here, but if you say so – and I give a quick goodbye and bolt back to the refuge of the apartment.

Caty and Aaron are awake, and I recount the whole thing immediately.  But they aren’t nearly as shocked and confused as I am.  In fact, it’s almost like they thought this was…normal.  “Wait, so you went on a date with a guy from Tinder, and you were shocked by all this?”  When you put it that way…

But I chalk the date up to a solid Game Over, since surely he’s feeling just as weird as I am, especially after being a bit rebuffed.  The next morning, I’m shocked to see:
Too weirded out by the encounter, I had to decline. I was astonished he’d followed up, but I wished him well and moved on.  Surprisingly again, he wrote me a nice little note in response wishing me well, too.

Not another word was said between us until nearly four months later, as I’m long gone from New York and the Tinder scene.

I had a hard time figuring out how, or if, to share the story of The Broker.  Was there anything here of substance, or was this simply a gratuitous (almost) kiss-and-tell narrative?  I suppose you’ll be the judge of that, but here’s what I took away:

When I first reflected on The Broker, I saw little more than a caricature of the typical modern dating man. And the most lingering memory was our awkward streetside almost-kiss battle of wills.  But as I kept trying to write about the experience, I couldn’t end on that note, because the almost kiss feels less and less significant the further I get away from it.  That’s when I realized that this isn’t a story about kissing.  I think it’s a story about taking a risk, and bouncing back.

Because like many of us I think, I’m incredibly afraid to fail and be rejected – the moment when someone will tell me, you’re not enough.  You didn’t make it.  I don’t want you.

But small as it might be, the fact that The Broker came back around after a little rejection was notable to me –  because I wouldn’t bounce back so quickly.  I’d hide in my comfort zone to nurse my fragile self-esteem back to health, then I’d make sure to steer clear of whatever had injured me in the first place.

In the face of failure or rejection, it seems like we only have these two options: take a step back to self-protect, or take a step forward, continuing to risk, believing that even if we lose, we’ll still be the better for trying.  I’m scared of the rejection that’s inevitable when we keep risking and stepping forward, but even more scared we’ll become small, alive yet unalive people if we always play it safe.

So tonight as I write this, I have a new-found respect for The Broker.  Because in the simplest terms, here was someone who didn’t run scared at the first sign of rejection, and I can’t help but admire him for that. And hope to do more of the same.  Because maybe a little rejection’s not nearly as lethal as it’s made out to be.   As I thought back to how he followed up with me after the date, I reached out to The Broker tonight, four months later.  And you know what? Seems like he’s carrying on just fine.  Maybe Kerouac also has something to do with it…


“The only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars.”

-Jack Kerouac, On the Road


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