The Ultimate Wingman: Dude…She’s Just Not Into You!

WingmanThe really cool thing about being a happily married 44-year-old guy is I can go places and just laugh at the length younger men go through to impress a woman. Don’t get me wrong… in the past, I’ve made a fool of myself on numerous occasions too. Luckily, I outgrew that immaturity and learned that what a real woman wants is an authentic man in which she can share interests. There is no other way to put it, I was definitely a piece of work.

The memories came rushing back recently after I observed a conversation in the optometrist’s office with three women. Here’s the situation, my wife, I, and two ladies were hanging out browsing the selection of frames at the counter. After discussing prices and styles for a bit, this flashy sort of guy walks in with his shades on. He had the kind of attitude that screamed we had obviously missed the signal to be impressed with his grand “Hollywood” entrance. So, he stood in the doorway as if to say, “I’m here for you ladies!” I can bet everyone reading this knows a guy like that and I’m sure every lady reading this can imagine exactly the type of guy I’m talking about.

But the story gets better (This is where it is important for every guy to be honest with himself)! Mr. Hollywood walks over to one of the women, sits down in front of her and says “I know you didn’t forget me, right?” But I don’t think he was ready for her to act as if he didn’t even exist. This always crushes our feelings, right fellas? At that moment, I leaned over to my wife and laughed. We both knew what was going to happen next.

We listened in amazement as he made every attempt to wow and put the “moves” on these poor women. He went on and on about why she should remember him since “he’s so tall and leaves such a huge impression on females.” I still have no idea how they managed to avoid bursting into hysterical laughter in his face.

After he finally left, obviously feeling a bit deflated, I got an earful of conversation that guys usually don’t hear. This was like being in the war room of the Pentagon as the ladies went back and forth ripping him apart; it was top-secret level information guys! It wasn’t long before I mentioned my book, The Modern Princess, which outlines the miscues of men and women in relationships. It was a perfect segue for the conversation. As it turns out, this guy’s epic failure would be a perfect lesson in what women hate and what every guy should avoid.

(1) He walked in but they never met “him”: Authenticity is vital to any relationship, especially with the ladies. If you’re looking to connect with anyone for more than a few one-night stands, cheesy lines are the worse. I must admit, it took me some time to learn to appreciate and value myself.  However, once I did, it enabled me to value the opposite sex. Ladies, when a guy refuses to show you who he is, he’s hiding something. Anyone can impress via their online profiles or for the first few dates. Real and lasting relationships are born out of an authentic and organic interactionwingman.

(2) He assumed she not only remembered him but somehow was impressed:  Wrong! Any guy that only wants to impress spells disaster in long-term relationships. Trust me when I say, that is who I was in my twenties! Once the freshness of the relationship is over, you will begin to truly see him for who he really is. Remember this… impressing a woman is for boys; grown men seek a connection at a deeper level.

(3) He tried to connect with her through material things:  These poor ladies struggled through his weak advances while he dropped the hint that he drove a nice car and was an entrepreneur. He even worked into the conversation how big his house was. When will we learn that a real woman is not a gold digger, she’s a goal digger? Please remember ladies, if he has to tell you he’s a “boss,” he’s not!

In the end, the joker gave us all some comic relief for the day.  The good thing is life, at its core, it is filled with lessons that are waiting to be taught.  In a few short moments, I was able to look back at my own life and see so many errors. But I could also look forward with a desire to spread hope through my books and coaching. Although he was funny, my true passion is to cultivate meaningful conversations about love, relationships, and all the other stuff that goes with dating. It should be a source of enjoyment, for all involved.

Written by Early Jackson
(Edited by Cherese Jackson)


Book:  The Modern Princess:  A 21st Century Guide to Fairy Tale Relationships

Photo Credits:

Top Image Courtesy of Early Jackson (New Direction Coaching Association)
Inline Image Courtesy of Ashleigh W – Flickr License
Featured Image Courtesy of  Deann Barrera – Flickr License