Shoe Game, Coffee and Not Having Sex

  • Life is about friends and shoes

“Hey man, I dig your monk straps. What are they?”

Did that just happen? Did this guy just use my line on me?

“Thanks, man. They’re Ferragamo’s. Picked them up in Florence last year.”

Few compliments are better than those directed at a man’s shoes, especially if he knows what he’s talking about. It’s a connection, a mutual admiration of craft, of history, of style. A guy that knows shoes, knows shoes.

That’s why I never fail to compliment another man’s shoe game. 

And now this kid’s reversing the role. He’s playing my game.

He offers me a seat and he cycles through the multiple Word documents floating on his monitor.

The conversation flows down stream and I’m directing the boat.

“I just recently moved to Chicago. Had to get out of town, start fresh, sail my ship to see what would happen. I’ve been blessed with some great opportunities so I try to take as many as I can, pushing for the risk and danger while I still can.”

He’s a got a spark, that’s obvious, but…

“You know, it’s a great city. I really like it. Although I am slightly worried for the winter weather. Totally different shoe game when the snow rolls around. But I’ve found it really hard to meet people. I mean, not people, but real people. It’s easy to sit down in a coffee shop and chit-chat, surface discussions, but beyond that, I’m not connecting with those I feel I need to be connecting with.”

Yup, that happens. 

“I know what I want to do, I have a pretty clear idea of my direction, I just feel a little stuck. It’s a weird year, you know. I’m trying to break out on my own, to do me, to understand who I am while pushing for a better me…”

He trails off into thought.

“It’s weird noticing how I think now as opposed to two years ago. It’s a definite, noticeable difference. And that’s just two years. From 22 to 24. What about 5 years? What will I think at your age looking back to now?

Nodding, I take a sip.

“Dude, no lie, I haven’t even slept with a girl in the four months I’ve lived here. It’s weird. I don’t even have the desire. I’m focused on me, on getting better, on figuring me out, I just don’t have time or mental energy for another. And it’s not like I’m looking to just fuck, that’s not what I meant, I mean, I just want a girl that’s down and bad to tear the city up with. It’s hard to find people to hang with, much less a bad chick.”


I’m not talking much, just asking questions, sipping my coffee and listening.

I’m not telling him what to do, what I think is happening in his life. Too many older people do that without permission. It’s usually shit advice anyway.

He’ll figure it out. He’s pushing, he’s searching, it will click. He’s in it, which is hard to see in the moment. Only looking back do we see how the cobblestones paved our path, after we trekked through the overgrown forest, hacking away trying to find our route.

We shake hands and I hand him my card.

“Keep walking. Keep making shit happen.”

I nod at his Jordan IV’s, a silent salute, before heading out to my meeting.

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