Zen and the Art of Real Estate Investing with Jonathan Greene

When You Realize You’re Not Trying Hard Enough


Photo by Adrian Swancar on Unsplash

Photo by Adrian Swancar on Unsplash

I don’t really want to date right now. But as each day passes I become less and less resistant to the possibility. However, in order to be open to it, I really have to put forth a modicum of effort. Because right now, I’m not doing anything. And it’s not getting me anywhere.

Not that I want to get anywhere. Actually, if I am writing this maybe I do. Or maybe I will soon. It seems that my dating antenna always gets tweaked while I am at Starbucks. It’s not like I hang out there, but it is part of my after-school routine on the way home with my daughter. So, I’m there. A lot.

I also don’t do much else, so the only opportunities for me to be reminded that there are beautiful, intelligent, and down-to-earth women out there usually happens at Starbucks. I talked about this phenomenon when I decided to quit Internet dating for good. And now it happened again.

What Woke Me Up

I left my house to pick up my daughter, as I do every day, at 2:00 pm. Most days I’ve showered by this time, but some days I haven’t. And when I haven’t I don’t even think about it. That’s part of the problem. I interact with so few people each day that the act of showering isn’t a prerequisite for going into the world.

So we make the stop on the way home at our trusty neighborhood Starbucks to wildly overpay for iced teas and a chai latte. My daughter is tired so she waits in the car as I fetch our three drinks (one for my son as well). Again, I don’t think twice about rolling into Starbucks in gray sweatpants, a heather gray sweatshirt, a jacket, mismatched socks, my glasses, and a ratty, old U.S. Open baseball hat.

I go to the mobile order pickup hotspot, but in an act of universal malfeasance, our drinks aren’t ready. I routinely order them when we are 12 minutes away and the prep time is 3–8 minutes, but sh*t happens when school lets out and 8 kids all want a frappuccino at the same time.

I’m standing in a daze, relegated to the normative nature of my daily routine. But then I see her. No, it’s not the same woman from the last time. She might be with her mom, she might be with a friend. She’s in my age range and extremely attractive to me at first glance.

She’s looking at me in all my glory. Sweats from head to toe. Dirty hat. Legend. I don’t know why she’s looking at me. I still don’t. Maybe she was shocked at the length of my beard now even though we’ve never met. But she does have a familiar look.

Maybe I’ve seen her online in the past before I quit. But if so, she would hardly recognize me in my pseudo-gym, lazy Dad of the Year gear. So, what gives? Is it possible she finds me attractive? Does she think I just had an epic workout? Is she sad for me because I appear to be out of work and overspending on luxury drinks? I just don’t know.

But damn. She fine.

Even in my state of general disheveledness, I perked up. Who was she? What’s her story? Does she have kids? Why haven’t I seen her before? And why the f*ck am I dressed like this the first time I see this beautiful person?

It was then that I realized that I wasn’t trying hard enough. Actually, I wasn’t trying at all.

Trying At Life

I have to be honest with myself. My IDGAF attitude about how I present myself right now is downright embarrassing. For ten years, I wore a suit to work and obsessed about the shirt and tie combinations every morning. Now I go to Starbucks at 2:55 pm wearing the same sh*t I slept in. I’m not trying.

But she was trying. At life. She looked casual but put together. Mature, but sexy. Alluring but oblivious, kind of. She wasn’t oblivious of me for some reason. And I definitely was not of her. But she was trying. And I was hiding.

It’s not that I’ve given up on dating, but after more than a year of ignoring love, I guess I’ve really let myself ignore life too. It’s not the first time I’ve noticed this about myself in the past couple of months. Even when I shower early, I still put on the same jeans and some hoodie that’s laying around.

I’ve been writing a movie where the main character, a founder of a startup, is in his light thirties and always wearing a hoodie. He literally gets sh*t the whole movie because of it from his sister. And his niece. And his friends. And just as our writing is a projection, sometimes it’s a finite projection of ourselves. He is me. I am him.

They were messing with him because he wasn’t trying. I’ve been messing with myself because of the same.

Why I Needed This Wake-Up Call

I needed it because I need to remember that I am allowed to have a life. As a full-time dad, I sometimes forget that it’s acceptable. Or maybe I’m just being intentionally forgetful. Because when I can’t remember that I can have a life, I don’t have to try. I can stroll into public in the mid-afternoon in what amounts to adult pajamas without giving a f*ck.

But this wake-up call is a reminder that I really do GAF. And it’s not just about going on a date. Or meeting someone. It’s about hope. The hope I felt that last time at Starbucks. And the hope I felt this afternoon. The funniest thing is that the woman could have been looking at someone behind me today. But it doesn’t matter. Because I felt something.

For someone like me, at this stage in my life and considering my parental responsibilities, I need multiple reminders to feel something. I needed this wake-up call because I wasn’t trying hard enough. Actually, I wasn’t trying at all.

Until tomorrow.

3 Responses

  1. I enjoyed this read. (F, 23) although this was about your issue of not trying hard enough in your personal life, it resembled a lot about my own mindset at the moment in my life. Needing change and a wake up call. I enjoyed that it was short and meaningful.

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