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Want to stay single? Take dating MORE seriously.

The shocking twist I learned while dating in my 20's...

No, that’s not a typo. You read it right.

Since high school, I would look enviously at couples in public. I saw them having a cute date in a coffee shop where she slowly paced her foot up and down his shin.

I’d see him sling his arm around her in church and whisper small observations into her ear throughout the sermon.

She likes you.
He likes you.
You like each other.
You’re so freaking cute.
Go home.

I listened to endless romantic songs, despite being single for 99% of my life. It was just what I wanted so badly.

You hear the trite maxim like “Once you stop looking so hard you’ll find her,” and roll your eyes and sock the speaker in the mouth. Because how are you ever going to find the love of your life without active searching, online dating, approaching every attractive stranger, and desperate sobbing into your pillow??

Something shifted inside of me around the time I was 27 or 28: I realized that I began to date less seriously.

It’s ironic.
You’d think that the older I got, the more seriously I’d take it.
Time is of the essence.
Every day is another step toward my grave.
Get married soon so you have as much time possible with your beloved.
Or else life is a waste.

Vanity of vanities: a life spent single??

When I was younger, I graduated high school and told myself, Okay Buddy, you’re out of high school now…time to date seriously.

Now that I’m 30, I’m just out here trying to have a good time. I know myself better and know what I’m looking for and I’ll know when I find it. Until then, I can enjoy the process and have fun dating—something I rarely did in my early 20’s.

But you know the best part, the shocking twist?

I think this attitude is more attractive. I’ve had much more success—far more second and third dates—by trying less hard and being less serious. People want to date someone who is able to have fun, relax, and enjoy the ride.

I scared away countless women by being so serious while dating them. “Ok, so let’s talk about where we are,” I’d say at the beginning of our second date. No wonder they didn’t want to date me! I was way too serious way too fast.

If you so desperately want a relationship, try less hard.

It was my desperation to fling myself into a grave and committed relationship that kept me from one for over a decade. I’d fall head over heels for a woman, decide she was the one for me, and then I’d tell her on our second date.

I couldn’t figure out why none of them wanted to date me. What do these other guys have that I don’t?? I would constantly ask myself.


That’s probably it.

They were able to date, and have fun dating, for weeks before initiating the grave Define-The-Relationship talk.

I mean, it’s so strange. I’m on and off dating apps more than a nomad hops on and off trains across the nation. And I’d like to be in a relationship sometime. But when I read a woman’s bio and it says something about “Only looking for something serious and real,” it’s kind of a turn off. Where is the fun? Where is the excitement of just getting to meet someone new and seeing what happens? Her bio doesn’t make her seem like an especially fun, curious, adventurous person…just like me for most of my 20’s. No wonder no one wanted to date me!

I’ve always been an incredibly fun, excitable person, except in this one area—I always got so serious so fast. After dating me, women likely asked,

Where is the fun? Where is the excitement?

Want to stay single? Get serious real fast when you date.

Want a relationship? Slow down. Be patient. Enjoy the process. Have fun.


1 comment on “Want to stay single? Take dating MORE seriously.

  1. Really enjoyed this!

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