The Ultimate Wingman: 5 Reasons She Did Not Give You a Second Date

manWe live in a world where everyone wants an edge. From sporting events to boardroom business deals, the competition is ridiculous when it comes to being a guy. No wonder this year’s Super Bowl commercials broke record after record; we all want to influence and gain the advantage. Even in the area of relationships, guys around the world are literally using everything they can to meet, date or just hook up with the woman of their dreams. In fact, if you haven’t noticed, online dating websites have gone all in on the advertisements. eHarmony, SinglesMeet.Com, Zoosk, and Match.Com are making their way into people’s lives every day right in the middle of our favorite programs. This is why I wanted to focus some attention on the fellas for inspiration.

For the last two years, I have been on a campaign to empower women. I wrote The Modern Princess: A 21st century Guide To Fairytale Relationships specifically for the ladies. As a father and grandfather of young ladies, it was imperative for me to offer some solid advice amid such decreasing standards. One peek on social media will prove we are in some serious trouble where relationships are concerned. This book was just my way of penance for being horrible when I was younger. But recently while out with friends, the guys got on me about leaving them unrepresented. We laughed about how important it is to have a friend, a sort of wingman to hang with and keep you out of trouble but most of all, be another set of eyes to develop a strategy to get the right girl. We joked around about a service to hire out to guys so they are never without the ultimate wingman. That’s when the ideas started flowing.

First, let’s define a true “Wingman” shall we:

  1. A pilot whose aircraft is positioned behind and outside the leading aircraft in a formation.
  2. A guy you bring along with you on singles outings (like to bars) that helps you speak, meet and eventually date a woman.

So, you finally did it. You’re out with the girl from the gym you’ve been eyeballing on social media. You liked 20 of her pictures back-to-back and, at last, she acknowledged you. After another week of using a machine that you hate in the gym, you ask her out for dinner… and she said yes. Your best shirt, a trip to the car wash and a few minutes later, the evening is over. Of course, you wait a couple of days to reach out, but you get nothing back. You see her in the gym the next day, but again, nothing but the cold shoulder. Now you’re in a panic because you have no idea what you did wrong. Where did you miss it? What land mine did you step on that evening that makes her not want to see your face again? This is where your “Wingman” comes in.

Guys, I am here to share the top 5 reasons she just isn’t calling you back. Warning!! You may not like what I have to say, but you need to hear it.

(1) You’re just not ready to date a grown woman: Let’s start this off with a bang. Most guys I have the chance to coach are still bent on playing childish games with women. That doesn’t work in this fast paced, tech savvy world we live in. Childish games are like Kryptonite for a successful, smart woman. In fact, she can smell your junk a mile away. A lot of guys want to be dishonest, play the field or just plain run game on a woman and have the audacity to get pissed off when she calls him on it. Own your junk, tell her the truth and, for God’s sake, ditch the petty childish games.

(2) You’re not believable: If you don’t believe you, no one else will. When you speak, are you coming from a place of authenticity and truth? Or are you just a walking contradiction that screams “Player?” The way you come across to others is so important in the dating world. I’ve had women tell me that they’d rather a man be brutally upfront and honest about situations than play with their emotions. At least, that way she can respect your words and not see you as a total jerk. There’s no shortcut or secret to this. You are either a truthful, believable person or you’re not.

(3) You still think material things equal attraction: Don’t make me laugh! We live in a time where women are out there hustling harder than some men. Do you really think she can’t afford her own car, home, or drinks for that matter? She absolutely can. The real deal is she is looking for someone to connect with on a level far deeper that a new bag or a trip to the spa; that’s stuff she can do for herself. She longs for a companion with whom she can share her dreams, frustrations and fears. She wants arms she can feel safe in. All the other stuff is just dressing on the tree. So don’t insult her intelligence by flashing a few dollars and expect her to melt away for you.

(4) You think it’s all about you: Dating someone self-absorbed is draining. It takes its toll on your wellbeing. A narcissist makes for a terrible dinner date. She doesn’t want to sit across and have a conversation with another Kanye West while being forced to hear about what you’ve done, how wonderful you are and what makes her so lucky to be out with you tonight. That gets old quick. If you are out on a date and doing most of the talking, you’re already blowing it! Shut up. Ask probing questions and then listen to the answers. If you let her, she will tell you where the key to her heart lies.

(5) You’re obsessed with sexing her: What are you, sixteen? By now you’ve got to know that spending the evening trying to get into a woman’s pants rarely works in your favor. The whole night, all that’s been on your brain was how to get her back to your apartment; this is the exact reason she won’t end up there. Let me tell you something you should have figured out a long time ago. If a woman is going to do anything with you, it will be on her terms, not yours. Wasting time trying to coax her into the bedroom is so tacky. Get to know her. Make the investment into a relationship and see where things are going before intimacy takes over your brain. She’ll thank you for it.

Whether we are talking about Eric from Entourage, Buzz Lightyear from Toy Story, Walter from The Big Lebowski or go way back and mention Goose from Top Gun, the concept of the “Wingman” has proven to be beneficial. These men will go down in history as earning their title with honor. As you prepare to face the woman of your dreams (or just maybe your dreams this week) I want you to know I am here for you. Getting to the date is only the first step. The hurdle is getting to know her, and, of course, inviting her to know you, and seeing if this is a person you want to start building a relationship with. Whatever your deal is, just think of me as your Ultimate Wingman who is along for the journey.

Written by Early Jackson
(Edited by Cherese Jackson)


Book:  The Modern Princess: a 21st Century Guide to Fairytale Relationships

Photo Credits:

Top Image Courtesy of Early Jackson (New Direction Coaching Associates)
Featured Image Courtesy of Jeremy Keith – Flickr License

5 Responses to "The Ultimate Wingman: 5 Reasons She Did Not Give You a Second Date"

  1. early jackson   March 3, 2016 at 6:10 am

    Hey there Phil! Thanks for the comments. For me, a wingman is the guy that comes along side of you and share experiences (both good and bad) to hopefully give insight on dating. Of course I feel dating should be strategic and not just a random exercise in hooking up. So a wingman can be a vital extra set of eyes to point out blindspots. Then we can make the adjustments and grow.


  2. Phil Dorrington   February 27, 2016 at 11:47 pm

    I get the impression from some women that they have no desire whatsoever to understand what it’s like to be young, human & male, revealing ones inner thoughts to such a person typically seems to result in being thought of as “Juvenile” that the youth, humanity & manliness are character flaws to be expunged. I suspect these people to be Closet Lesbians, perhaps hiding in the Closet from themselves.

  3. Phil Dorrington   February 27, 2016 at 10:24 pm

    I posted something similar here a few times, but it didn’t come through & didn’t give me a “awaiting moderation” message, so if the duplicate posts do appear, i hope it will let me delete them.

  4. Phil Dorrington   February 27, 2016 at 10:21 pm

    Perhaps he is sub-consciously self-sabotaging his own efforts, he may be aware of the effect his actions have, on a deeper level. Marriage appears like a Pyrrhic victory to me & i’d think it would have to be thought of as a genuine victory to succeed in most cases. Still, if a guy or gal waits long enough, it seems he / she is mostly abandoned by their “mates” before they have to suffer the feeling of abandoning their “mates” – not sure which is better really, to feel abandoned or like a deserter. Then they may start to feel they are becoming irrelevant to the living, whether they want to feel “relevant” to the living enough to overcome their relationship objections is another question. I’d have thought a “Wingman” who’s advice was to be serious about seeking a life partner, wasn’t really being a “Wingman” at all, more like some sort of relationship Guru.

  5. Phil Dorrington   February 27, 2016 at 9:01 pm

    I’d have thought a “Wingman” would be the sort of gimmicky trick that would set her Bullsh*t detector wailing, or might she be impressed that you bothered to put the effort in, at least? Seems the “Wingman” is largely thought of / expected to be an expendable companion, a temporary friend of convenience, for perhaps some small gain.


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