Why the book? (Chapter 1)

Prior to 2022, the last time I actively tried dating was 1993. I had moved to San Francisco in early 1993 and was starting my adult life. My goals were fairly simple and probably normal for any kid in their early 20s just getting started with their adult life: Find a decent job and find a partner.

The job-finding part went fairly easily. I found one in weeks, and a better one about six months later. But the dating was a failure. I tried meeting women at parties, playing various sports, while riding mass transit, starting conversations when the situation allowed, and through friends. In those first few years, I didn’t go on one date.

A big part of my problem was me. I’ve never been good at dating. I’m a great opener. I can speak to anyone, get a conversation rolling, and make people comfortable. But I’m a terrible closer. I have no sense of when someone may be interested in me, and I just can’t pull the trigger on asking someone out.

In high school and college, my friends would always want me to go out with them because they knew I could get the conversations started. Then they would always take it from there and end up going home with someone. Never me, though. (I once brought a woman to a college party, and my friend ended up taking her home.)

Like many in the pre-remote work times, I finally met the woman I married at work. We tried dating and broke up after a few months, but reconnected after a significant life event that brought us back together. We got married just over a year after that and were married for 25 years. But we both now agree we should’ve never gotten married. I think, at the time, after going so long without dating, I figured if not now… never.

Fast forward to July of 2022, when our divorce was finalized, and things had changed quite a bit on the dating scene. Instead of trying to meet someone out in the real world, dating apps had established a foothold in singledom and seemed to be what singles were embracing (or just to what they were resigning themselves…)

In July, I got on Bumble, and within two weeks, had met someone I dated for a year. At one point, I thought she was going to be it, but the negatives got insurmountable, and we moved on.

However, as it related to dating apps, my lesson was “this is easy!” At least, that’s what I thought in July of 2023. We’re now heading toward three years, and it has been nothing but one-and-dones, with perhaps two or three exceptions of a pairing that lasted two or three dates and one nearly two months. 

One thing I like about dating apps is it helps me get over the hump of my intent. If I’m matching with someone on a dating app, it’s clear my intention is to meet them, spend some time together, and see if we might have something. I’m no longer stymied by my inability to assess interest or get over the potential embarrassment of presuming someone likes me when they clearly don’t.

But even with that advantage, I’ve been amazed at just how “wild west” it is in the apps. There doesn’t appear to be any consistent etiquette. There’s no grace. No understanding. No clear rules of engagement. 

People’s expectations are all over the place, and it’s obviously impossible to know what anyone is thinking: Especially when we’re texting with someone we’ve never met and who may not even be the person you’re seeing in the profile. 

So after three years of experiencing and observing 1000s of profiles, connecting electronically with a few hundred women, meeting at least 100 of those across three states (Washington, Utah, and Wisconsin), and still coming up relatively empty-handed, I thought I’d take a shot at establishing some guardrails or ground rules that may help us all be more human in this digital environment. 

My regret with this book is that I’ve only been seeing and experiencing profiles and prospects from a male point of view. While I’ve seen many men’s profiles and have heard many insane stories about their experience with men (some of which are captured in the book) through my single female friends, I still wish this book were a bit more balanced by the gender-specific experiences and nuances. 

There was a time when I had a woman lined up to write this with me. I met her on Bumble when living in Wisconsin, and we hit it off right away. Unfortunately, she lived three hours north of me, and the logistics weren’t in our favor. Even more unfortunate is that after committing to help me drive my car back to Seattle, where she’s from, she disappeared to Ohio the day we were to start the drive without a word and was never heard from again. (That’s its own dating story.)

After that setback, I decided to continue on and publish the book in hopes I could help us all establish some sort of expectations and, if nothing else, help us all have a little more grace for one another on the dating scene.

Dating apps have fundamentally changed dating. And while they make it easier in some ways, I don’t think anyone really knows how best to go about it, make sense of it, or walk away with a productive relationship. Dating has always involved varying degrees of difficulty, depending on the person, and I hope this helps us all be a bit more patient and gracious with one another as we try to get in and out of it without making too much of a mess.