Dates Without Apps

My exploration of the Cold Approach

At my core, I’m a romantic. That’s why Good Will Hunting is one of my favorite movies. Every time I watch Will stand up for Skylar, who is being harassed by a know-it-all Harvard student, my heart rate increases. When she gives him her number, I’m filled with hope. And when Will smacks the window of the bar—the sticky note with Skylar’s phone number on it between his palm and the glass—and asks the bully “how about them apples?”, I smile from ear to ear.

So, when dating apps like Tinder and Hinge took over dating, I despised them. I saw them as prioritizing looks and brevity over depth and banter. They were ruining the chances of Good Will Hunting-type love happening. And I believed that people who used them were cowardly, lazy, or both. Whenever the apps were brought up in conversation, I let everyone know my distaste for them.

Then, I became single.

I was living in Chicago, working 60 hours a week, and didn’t have many friends there. Getting to know people through repeated exposure, like in university, no longer existed. This made cultivating new relationships outside of work challenging. When it came to dating, my only options were meeting women in public, at work (that was a bad idea), or via Hinge.

Approaching attractive women while sober scared the hell out of me. So, it took a lot of “liquid” for me to gain the commensurate “courage” to ask someone out. That left me no other option. I put my hatred aside and downloaded Hinge. Did that make me a coward? Maybe a little bit, but I needed to find true love.

After a few months of limited success, my hatred returned. I was spending a lot of time on the apps without much to show for it. Women I deemed attractive, that I believed were well within my league, didn’t feel the same way about me. This was a blow to my self-esteem. Had I lost every ounce of attractiveness? Was I no longer interesting?

After analyzing my past relationships, I quickly realized that they had all sparked from in-person interactions. This meant that my best qualities – my personality and sense of humor – were being de-emphasized by dating apps. Meanwhile, my deficiencies (I’m 5’7” and was 20 lbs heavier then) were spotlighted.

I decided it was time to figure out how to create a Good Will Hunting-type of love for myself. So I started looking into how to meet women in public, and came across Neil Strauss’s books The Game and Rules of The Game. Neil is also 5’7”, so his success with women gave me confidence that I could figure it out despite my physical limitations.

Rules of The Game offered men a way to emulate Neil’s “pick-up” game by following a 30-day “social workout” plan.

Day 1: “Look 3 people in the eyes, noting their eye color.” Easy.

Day 6: “Give four women spontaneous comments. Two of them can be people familiar to you, but two have to be strangers.” Less easy, but I’ve got this.

Day 7: “Approach three women using one of the opener routines in the back of the book.” I’m too busy scared to do this.

After looking at Day 7 for thirty seven days, I finally mustered up the courage to carry it out. It went terribly, but I did it. After years of dreaming about meeting a cute stranger in person, I finally did it. While I had moderate success with this approach, I never got comfortable with it. The opener routines, while otherwise harmless, were always based on a lie. An example:

“My friend and his girlfriend are exclusive, but he found out that she sometimes makes out with women when she goes out on the weekends. You look like you might be an expert on this - do you think this is cheating?”

If the woman expressed any Indicators of Interest, or “IOIs”, after the opener discussion, the next step was to move into a “value demonstration”. This is where I typically got stuck because of how ridiculous these concepts were. The least egregious one was called the “rings routine”. It required that I pretended a friend of mine had showed me how to interpret a woman’s personality based on which fingers she wore her rings. Another was a magic trick. A third was a riddle involving a penny, a dime, and a nickel. I never bothered learning more because I almost never used them. When thinking about going through the rings routine again, I make the same face as when someone passes gas on an airplane.

I couldn’t get comfortable with these concepts because they were inauthentic. I was putting on a show to get women to like me—just like what was required to do well on dating apps. Worse, I had adopted the same mindset: choosing who to approach based solely on looks, not personality, shared values, or interests.

Pick Up was supposed to put me much closer to creating a Good Will Hunting type of love than dating apps. In reality, they were one in the same—both incentivize a level of artifice in order to achieve the desired outcomes.

This discovery led to a renewed approach to meeting women in person. There are two key changes that have led to two positive effects.

Changes:

1. Mindset: I’m no longer focused on the outcome of getting a phone number. My goal is to learn about the woman first, before deciding whether or not it makes sense to ask her on a date. If there’s something that connects us, I’ll ask for the number.

2. Process: I used to go places I’d never go otherwise (e.g. the mall, yoga classes, grocery stores) just to meet women. Now, I only go places I need or want to go, and meet women as a byproduct of my social activity.

This has had two positive effects:

1. Less nerves, more authenticity: I now see approaching a woman as an exploration of curiosity instead of a performance act. My self-worth is not being put on the line every time I try to meet someone new. My most-often used opener nowadays? “How are you?”, and a smile.

2. Increased focus on connection: When using Neil’s teachings, looks dictated whether or not I approached. My focus now is more holistic. Of course I still want to be attracted to my partner, but compatibility and rapport matter just as much as attraction when it comes to finding a life partner. Since implementing this new approach, I’ve refrained from asking several attractive women out because something else about them informed me that they would not be a good match.

Over the past 5 months, I’ve gone on 20 dates with six women using this approach. I can confidently say I’m closer to creating a Good Will Hunting-style love than I’ve ever been before.

This journey hasn't just transformed my own dating life. After participating in Integrated Men for 2 years, I found myself naturally sharing these insights as a small group leader for single men under 40.

Watching their dating lives transform through authentic connection has been rewarding. If you're struggling with the same challenges I faced and want to create your own "How do you like them apples?" moment, I'd be happy to help. Respond to this email to learn more about working together one-on-one OR book an intro call.

Look out for my next essay - There, I'll break down the specific elements of this approach: the questions I ask, the mindset shifts that make conversation flow naturally, and how to recognize genuine connection when it happens.

Curiosity Corner:

1. What prevents you from approaching people in public?

2. If you do approach people in public, what tips, thoughts, or concerns do you have to share?

3. If you’re a woman,

   1. What makes you feel safe when being approached?

   2. What makes you interested in learning more about the man?