I wish I could say that I talked to a ton of women yesterday and today and had dates lined up for every day this weekend. 

But the truth is I didn’t approach a woman yesterday. I saw quite a few. I tried to work up the courage. I balked every time. 

I still don’t consider yesterday, or my challenge, a failure.

There have definitely been times in the past I would have.

I would have shamed myself for not delivering on what I promised. I probably would have given up on my entire 90 day challenge. I might even have deleted my blog, rather than admit failure.

I definitely wouldn’t have rebounded by approaching one today

This whole challenge is about learning and growth. 

If I packed it in, that would have been a failure. If I approached 90 women but never grew, that would have been a failure. But as long as I keep learning, growing, and trying, I can’t fail. 

To cement my learning and growth, here are 3 things I learned not talking to a woman yesterday, 2 things I learned talking to one today, and 1 thing I’m going to try differently tomorrow.

A lot of my fear is centered around the uncertainty of the outcome

Yesterday I was at a coffee shop and saw an attractive woman walk in with her partner. I looked up a short time later, and there she was, standing in front of me looking at something, no partner in sight. I thought ‘I could talk to her, and that would ‘check the box’ for my challenge.’

I didn’t, but I did realize that it felt less threatening to talk to her because I already knew her answer. Since I knew she was going to say no, it gave me an illusion of control over the outcome that I wouldn’t have had talking to a woman somewhere else. 

I often assume neutral responses are negative

As I was walking home from the coffee shop, I saw another attractive woman heading toward the train station. I looked back a few times, but didn’t make a move. Just before she stepped onto the escalator, she paused and looked at me. In my mind, her expression said “what do you want you creep?”

But when I think back on it, she didn’t have a negative expression on her face. She didn’t have much of an expression at all. I interpreted her neutral expression for negative, and didn’t bother to say anything. But it could have just as easily been curiosity. And maybe she was pausing to give me an opportunity to say something.

Unfortunately I’ll never know.

Approach things with a growth mindset

I read Carol Dweck’s excellent book Mindset a few months ago, and have been trying to implement a growth mindset in my life. 

In a fixed mindset, not approaching a woman on Day 1 would have ended the challenge. I would have told myself that I didn’t have what it takes. That if I couldn’t approach even one woman, I was never going to be able to. 

I might as well go back to dating apps.

The growth mindset focuses on each setback as a growth opportunity. Sure, I wasn’t ‘successful’ yesterday. But I know with the right tenacity I’ll be able to grow and improve in this area.

I can only catch up, learn, and grow if I stick with it.

Today, I worked up the courage to approach a woman at the grocery store. I told her I thought she was pretty cute, and wanted to introduce myself. We chatted briefly, and went our separate ways.

Here are two things that experience showed me:

Nobody cares what you do

The grocery store was pretty crowded while I was there. There were a lot of people waiting in line. I knew, just knew, that if I approached her everyone around us would stop and stare and judge me. 

I don’t know if anyone even turned their head. She was in line checking out with a friend, and her friend didn’t seem phased at all.

Everyone was in their own little worlds, and I was trapped in mine.  

It was a way bigger deal to me than to her

As someone who never approaches women, this was a huge deal for me. 

My heart was pounding in my chest. My body caved in on itself. My posture was probably terrible. I don’t think I annunciated that well. 

It seemed like just another Tuesday to her. 

Maybe she gets hit on all the time. Maybe she doesn’t. I made it into this incredibly big thing in my head. Her calm, polite response told me that it wasn’t a big deal for her. 

So maybe next time it doesn’t have to be quite as big of a deal to me, and I can

Ask her out

When I ran out of things to say today I just said “nice to meet you” and walked away. I didn’t ask for her number. I didn’t give her mine. I didn’t ask if she wanted to get coffee, or a drink. 

I’m absolutely proud of myself for going through with it and approaching her. I think I’ve done something like that less than 5 times in my life, and certainly not in many years. But this isn’t just about talking to women just to talk to them. 

So assuming I can find the courage tomorrow, I’ll actually ask her out.