Approaching Women: The Simple Event That Changed My Life

Copyright 2006 X & Y Communications

It was a perfectly normal Saturday afternoon. I was going to visit my girlfriend later in the day, but until then it was time to run the usual slate of typical, mundane errands.

Even though I was in a relationship at the time, I had learned from my research on men and women that ‘style’ was important—so I had some nice jeans and a button down shirt on. My belt and my shoes matched, and I was in “Successful Guy Saturday Casual” mode.

After a quick trip to the post office and a stop at the bicycle shop, it was time to go to Target. I needed several things, so I got a cart.

I had checked off toothpaste, light bulbs and a couple items from the automotive department when I happened to see someone I knew at the end of the aisle. I had only met her once, but she was a friend of my girlfriend’s. So I knew I had better say “hello”. After all, “making nice” with the girlfriend’s friends is always a plus.

She didn’t appear to notice who I was, so as I reached where she was I tapped her shoulder with the back of my hand and said (simply), “Hey!”. She turned and responded back with a reciprocal “Hey!”, with a warm smile and that classic “eyebrow flash” that the body-language books talk about.

“So it looks like even superheroes like you and I still have to shop for normal, everyday stuff at the Target, right?”, I said, noticing a few stray items in her shopping cart.

“I suppose!”, she acknowledged with a laugh.

I continued with very typical small talk after that. As the conversation continued, I started feeling something strange…if not downright creepy.

My girlfriend’s friend, if my mind wasn’t playing tricks on me, was starting to behave in a manner that I would ALMOST call…FLIRTATIOUS.

I was caught off guard. After all, if what I was seeing was really happening, it was COMPLETELY INAPPROPRIATE. After all, not only was I dating this woman’s friend…this woman was MARRIED!

So I maintained that 18” distance that social mores dictate is proper, while continuing with perfectly normal conversation. But soon, there was no denying the body language. She was clearly enjoying the interaction, and eventually made a comment or two that were unmistakably forward.

At this point I was going OUT OF MY WAY to not appear romantically interested in return. Yet, I couldn’t help the thoughts that were racing in my mind. This woman was CLEARLY ATTRACTED to me. On top of the impropriety of it all, I was struck by the IMPROBABILITY of it all. This woman was 15 years my junior and at least FIVE INCHES TALLER than me!

Now, let me level-set here. My girlfriend at the time was a beautiful woman, and her friend was likewise very attractive. So here we had a situation where a woman who was NOT MY TYPE AT ALL, and indeed not one of the ones I would immediately picture going after a guy like me, was UNQUESTIONABLY INTERESTED.

At that point I realized that this conversation needed to end…and SOON, for obvious reasons. To that effect I said, “Well, time to get back to shopping. But I’ll tell [my girlfriend’s name] you said ‘hello’.”

There was a slight pause. Then a quizzical look from the woman.

“Uh…who’s [my girlfriend’s name]?”, she wondered. I looked back with an equally querulous expression. “…Aren’t you Jennifer?”

“Um…nooooooo…my name is Felicia.”

With my mind racing in several different directions, I happened to look down and noticed there was no ring on her left hand.

I spontaneously laughed, and explained to her what had just happened. The woman really was a dead ringer for who I thought she was.

She responded with warm eyes and a feminine giggle. “So that’s…IT…?”, she said with one raised eyebrow and a motion of the hand to indicate continuation. I politely ended the conversation there anyway, of course, because I had a girlfriend, and returned to shopping.

But I was changed forever.


I had read time and again about how something like 90% of men have some fear of approaching women. Furthermore, I had read about how the single most important factor in GETTING OVER that fear is to simply GO OUT AND MEET WOMEN. The problem is that most of the time we as guys can’t get out of our own way when doing so…assuming we get up the guts to even try.

So, in one brief exercise—and by TOTAL ACCIDENT—I had unequivocally proven what it takes to successfully meet women. Ironically, the “success” was OVERWHELMINGLY due to the fact that I wasn’t trying to “pick this woman up”.

So what’s going on there?

Let’s outline the key principles and components of that experience at the Target:

1) I had started the day making sure I looked my best. I was READY for an interaction with a woman…if not the woman at the Target.

2) I had NO HIDDEN AGENDA with this woman from a sexual perspective. There was nothing about my approach that caused her to put her guard up. I was just making normal conversation. As such, there was a comfortable atmosphere surrounding the whole thing.

3) Based on the fact that I believed I already knew this woman, I was 100% CONFIDENT that I wouldn’t be flatly rejected when I spoke to her. Think about it. If you behave as if you are sure that talking to someone will be met with a positive response, you will not be nervous or sketchy about it at all.

4) My “opener” with her was a simple “Hey!” with a light, backhanded whack on the shoulder. No fancy, contrived “lines”.

5) This was not a bar or some other special “pick up joint”. This was the TARGET!

Bear in mind that this woman, although very beautiful, was not at all the type of woman I would ever see myself approaching or see myself with. And consider that it took virtually no direct effort to impress her. What appeared to “impress her” was the sincerity and confidence portrayed in simply wanting to talk to her.


There is no doubt that this woman perceived my approach as being related to her being a woman and me being a man. Although I was not even close to who the “media” would match her up with, the combination of facility, confidence and a low-pressure approach WORKED WONDERS. Ladies, that kind of attitude is what you look forward to when it comes to men approaching you, is it not? Don’t shout me down for telling the truth!

After that day, I made sure that my “accidental discovery” became firmly embedded into my conscience. After that, talking to any woman I want—anywhere—has been all about considering her someone I already know, and affording her the simple respect that goes along with it. No woman has ever been a “stranger”, ever since.

Guys: If you have any trepidation at all when it comes to meeting a woman you find attractive, learn from this lesson and I assure you your life will be radically transformed. You have the ability to meet any woman you choose to. Make it so.

Ladies: Here’s to more guys learning what I learned that day. I know you all are patiently waiting…