Flipping The Dating Script

Nothing defines humans better than their willingness to do irrational things in the pursuit of phenomenally unlikely payoffs. This is the principle behind lotteries, dating, and religion.

Scott Adams

There’s nothing as informally structured, anxiety inducing, and unnecessarily complicated within our society as dating. You would think that with the amount of people in the planet and our overtly connected society we have developed our ability to interact with the intention of sharing a life experience would be something we have down pat. What makes it even more interesting is the subjective perspective we have within the entire courtship drama that is life, as men and women assume that their gender got the short end of the dating stick.

Men assume that women are at an advantageous position when it comes to dating, where the social norms places women at an obvious advantage from their perspective. And they might be right. Men have to openly admit their interest in a Lady by making their first move. They have to pick an activity and a location they think the woman would want to do. They have to amuse, entertain, and romance her; risking rejection at every step of the way, as the entire evening becomes little more than a performance for just one judge, one single person who holds all the power… the woman sitting across the dinner table.

And they say that working for Chef Ramsay is stressful.

A man’s perspective about dating is great and all till you sit down and ask a woman her point of view, as they can clearly explain why men have the advantageous position when it comes to dating. And they might be right as well. The man can go up to a woman to ask her out, leaving the woman in a position of having to wait till he decides that he wants to. He picks the place and the time. He plans it out. And the woman is left in a passive position as the only active participation socially accepted is held by the man. If traditional dating rules are to be followed, the best they can do to during the entire situation, and even to initiate it, is to send out hints of interest and approval.

And we know just how well people in general pick up on hints.

But what if we could change this whole messy and complicated affair? What if we could hand women the power of assertiveness they complain that they don’t have within the courtship ritual? What if we could ask men not to be so controlling, allowing themselves the ability to enjoy the ride and let go of the reigns?

Guess that you can!!! Some mad genius has called out the social bullshit that men and women complain about dating by promoting for a second year in a row September as “Take a Man on a Date” month!

And I say that he is calling out the social bullshit about dating because as much as men might complain that women are on the judging table in the dating equation, nothing is as challenging to a man as taking a passive participation in anything in life. And women might complain about men having the power within the dating scene, yet very few have confronted the terrifying scenarios of possible rejections, and its accompanying self-doubt and social shaming, that come from asking someone out.

That’s the beauty of modernity… modern women are confident enough to just walk up to whoever they are interested in, and be able to ask them out! That should be a simple side effect of being a confident woman. Who cares what people think? The wonderful thing is that for this month, you can blame it on it being September.

And Gentlemen…  Modern men should be confident enough not to be intimidated by strong assertive women! Be honored and flattered is a lady comes up to ask you out. You probably are able to relate to every single thought she must have gone through before walking up to you. Don’t fall back into a judgmental or arrogant mindset, as you should be able to empathize.

And Empathy should be the most important lesson within this month. Men and women are given an opportunity to step into each others shoes (and depending on how the date does, into much more) on what each other goes through in the dating scene. React as you wish the other gender would react to you. Who knows, this might be a great opportunity for people to start treating dating as something fun.

Dating Lessons From Casanova

I know that I have lived because I have felt, and, feeling giving me the knowledge of my existence, I know likewise that I shall exist no more when I shall have ceased to feel.

Giacomo Casanova

You might have noticed that for a Gentleman’s site, I post very little about dating or relationship advice. There are two simple reasons for this. First, Caballero’s main focus is self-betterment as a man. The second, I want to steer as clear away as possible from PUA (Pick Up Artists) strategies and philosophies. That second one does more damage than good to men, something I have mentioned before.

But from the perspective of the first one, I do understand that dating and relationships are an integral part of a man’s self-betterment, so dealing with those topics IS important. For that reason, I will fall back on the dating lessons taught by one of the Big Three Romanceers, Giacomo Casanova. (The other two are Oscar Wilde and Miguel de Cervantes)

But isn’t Casanova just a glorified Pick Up Artists, a depraved hedonist who took advantage of women? Blasphemer! That’s precisely what he wasn’t, as I explained in Casanova’s Condemnation of the Pick Up Artist. Then, if he wasn’t a pick up artist, how did he attain a mythical reputation for being one?

It was neither his sense of humor nor his good looks, which I can guarantee. He was a rather average looking man, and the idea that a good sense of humor will win over any woman is pretty much a lie. Last I checked, women weren’t chasing after clowns and stand-up comics. What he had in his favor was an abashed love for living fully and creating unforgettable experiences in a world trying to repress a person’s soul. How did he do this?

Privacy Is Key

Why were so many women willing to commit indiscretions with a man such a Casanova? Because they knew he would be discreet about it. He had no need to share any of his adventures with anyone, allowing them to feel that their reputation was safe, even as they shared time with him?

Why is this so important to mention as the first topic? Because we live in a world intent in showing off and publicizing every single meal and every gym work out; a world were discretion has become a rare quality indeed. We need to understand the importance of discretion once again.

Let Them Admire You Admiring Them

Dating exists within a world of self-conscious behavior were we constantly walk that grey line between appropriate and inappropriate actions. This has been getting worse every day as men are told that appreciating attractiveness is little more than objectification and expressing desire is admitting having sexual predatory instincts.

During that entire debate, one very crucial aspect is lost; our ability to let the other person know how desirable we find them. Without desire there’s no passion, so letting the other person know how we find them desirable, also lets them know how passionate we can be. And nothing is more alluring as someone blushing from that realization.

Ask Them About Themselves And Listen

I think I have expressed myself enough on the importance of listening to what the other person has to say, here, here, and here. Any more would be beating a dead horse.

Remove Judgement To Encourage Decadence

One of the most important aspects within this kind of rendezvous is how the person must feel at ease enough to be unabashed of their behavior. The only way to do this is by letting themselves act out without fear of being judged. How can they be free with you if you are constantly judging their every action? Create a space of free expression where they can break away of the self-conscious chains that they use every day within their regular lives.

Appeal to all the senses

In a world consumed with visual stimuli, were we filter our experiences through smart phones and computer monitors, shouldn’t we take the time to savor the full extent of what it means to have a human body? Understand how the senses create a full experience. Something as simple as a cup of coffee can become a full experience when you take into account the effect it can have in all your senses; as you become aware of the aroma, taste, and even the sound of its brewing. Extrapolate this awareness to every simple part of your evening.

Be Playful

We tend to take life WAY to serious, as everything has to become a social issue and a politically incorrect offense. We lost our ability to laugh, so anyone who shatters this armor also breaks our uptightness as well. THIS is why so many times you hear the comment about impressing women with humor. It’s not the humor itself, but the ability to let the other person relax.

Be Spontaneous

All too often we end up creating sterile, prefabricated and prerehearsed experiences within our dating life. “If it worked once, why not again?” becomes the usual mentality. The problem with this logic is that these experiences feel prefabricated and prerehearsed, as they ignore the reality that every person is different. Have a frame over which you lead your night, but be willing to scrap the plan without warning. Life’s most memorable experiences are usually the result of accidents.

Surprise Them With A Thoughtful Gift.

Yes, gentlemen. I am going there… I’m not talking about picking up the person with flowers, although I’m also not saying to avoid flowers.

If you are truly interested in a person, give them a token to make your intentions clear. Everything holds a message and a meaning, so this is your opportunity to say a lot without a single word.

On a side not, this token will remind them of the date long after the date has passed.

Rejection, The Online Dating Edition or "What The Hell’s Wrong With Guys Today?"

Most fears of rejection rest on the desire for approval from other people. Don't base your self-esteem on their opinions.

Harvey Mackay

A couple of days ago, a post was forwarded to me by a female friend asking for my opinion. The  basic idea of the post? As the article opening statement clearly mentions: “Man gives attention to a woman. Woman expresses her lack of desire for said attention. Man immediately turns hostile.” To read the full article, click here. My friend’s question was pretty simple.

What the hell’s wrong with guys today?

In actuality, her comments were a little more complex and involve several phrases that would shame most experienced seamen, but that’s neither here nor there. To be honest, I can’t really blame her comments as I have noticed how common this behavior is in the online dating circuit. It’s common enough to merit the Internet’s attention by exposing this behavior in previous articles like this one and this one. After looking this, and plenty more information about the subject I ended up with just one question in mind.

What the hell’s wrong with guys today?

Sure, we could blame a patriarchal society, male entitlement, and sexism. Everyone else seems to do it. But to be honest, every time people place blame on such abstract concept, it’s usually so they don’t have to think about an issue and find a more tangible cause and solution, it’s little more than a cop out.

So I started thinking about it, why can’t any of these guys (note that I will neither use the term men nor gentlemen when speaking about these guys) take the hint that the lady in question isn’t interested, nor why can’t they accept a simple “No.” What’s the emotional and social baggage that makes them incapable of dealing with rejection? And that’s when it hit me. The key word to find an answer isn’t “men,” or “sexism;” it’s “rejection.”

Please keep in mind as we move forward that I’m not saying that these guys aren’t sexist. What I’m saying is that they turn hostile (hurt) due to a rejection. They probably would have shown their sexist colors anyway later on. Also this isn’t your typical man, as most men aren’t like this. Unfortunately, today’s social media lives by feeding you with the worst case as if it was the typical case. We eat it up, share it out, and relate to it because who can’t relate with the idea of dealing with that one asshole who ruined your entire day?

But back to the topic in hand, why do these guys act this way? Because we trained them this way! Just take a second, stop thinking about the actual event and think about what we have been taught about dealing with rejection. They usually come in two varieties.

“Never take ‘No’ for an answer. Rejection just means you need to try harder.”

or

“It’s not that you’re not good enough. It’s that the other person failed to see what you had to offer”

These might sound like wonderful and inspiring life messages until you think about their effect on a person’s behavior. The first one teaches you that ‘No’ is unacceptable and that whenever you get that answer, you just need to try harder and more aggressively to achieve your success. Nice lesson to learn is a society where consent is so important whenever you are interacting with anyone. The second one teaches you to blame everything on everyone around you and their rejection is viewed as an attack based on the other person’s issues. Then we wonder where our current attitude of entitlement comes from.

We have these lessons drilled into our minds since we are kids. How many times have we heard a Mom tell her young boy that he’s special, and if the other kids don’t want to play with him, it’s their loss? (while glad that her wonderful son is no longer dating that tramp) How many times have we heard a Dad tell his daughter that she’s too good for the boy who dumped her? (while secretly planning the jerk’s demise)

But why do we see this behavior typically from guys? It’s not that women don’t have their fair share of assholes. It’s that in our current social behavior it’s the man who usually does the opening move. Due to this, the numeric probability is that you will see more male assholes than female assholes, at least in this specific scenario. It’s not that women don’t do the same, as there are plenty of stories of gals questioning a man’s masculinity as soon as he rejects her.

So how do we keep this from happening, or at the very least lessen the probabilities of this happening? We could start teaching our kids to deal with rejection from a positive perspective. We need to stop teaching how to handle hearing the word ‘No’ in a way that the person doesn’t feel insulted. We need to stop measuring our self-worth based on other people’s approval.

Do We Really Let Men Be Better?

I have often wondered how it is that every man loves himself more than all the rest of men, but yet sets less value on his own opinions of himself than on the opinions of others.

Marcus Aurelius

For the longest time since I began Being Caballero, I was confused over who my main audience was. When I looked at Facebook’s media matrix, I just couldn’t understand how my largest audience was men between 25-45, yet they were the ones who least “engaged” with my posts. I saw how “Dating Advice” or “Business Empowerment” sites had better movement among my main audience. I actually considered redefining out target mission because of it, especially since a few of these sites had approached me a couple of time. That’s till I received a message from “Andrew from New York.”

Mr Caballero, As a 30 year old newlywed I often find myself thinking about the kind of person, the kind of man I would like to be for my wife and future family. I just want to tell you how much I appreciate your thought-provoking writings about character and all your shared nuggets of wisdom. Your content is in its own class, and so refreshing in a sea of click-bait noise and "list" articles that do nothing for the soul. Please continue to do what you do and know that you are making a tremendous impact. Thank you, Andrew

Before you all think I post these kind of private messages as a habit, I actually asked his permission beforehand. We get those every once in a while, usually keeping them private. Yet this one was different, since as I wrote my response to his message I came to an epiphany. It’s not that men don’t want to become better; it’s that we have told them that wanting to just be better is wrong and something to hide.

All these “Dating Training” or “Business Empowerment” sites and workshops provide men with an excuse to be better, as they offer an endgame mentality. Train with them, you’ll get more women or follow their system and you’ll make more money. Both of these pursuits (women and money) are actually more acceptable within our society than wanting to be a better man. Ironically, neither money nor casual relationships are a true measure of the kind of man you are. We, as a society, have made men think that wanting to be better is an admission of weakness, that there is something wrong that you need to fix.   

Let’s do a mental exercise so I can better illustrate what I mean.

Let’s take a good look at “John” and what we have taught him about being a man. John love poetry but is afraid to let his friends know about it, as they will probably ridicule him. He will hide his online history from everyone, not because he is searching porn, but because he doesn’t want anyone finding out his reading list. He posts online using a pseudonym to avoid anyone knowing about his talent. He will sneak into composition and literature classes yet will hide in the back of the classroom to avoid anyone noticing, specially the teacher. He will go to poetry readings, yet will hide out in the dark corner of the club. When his friends find out about his interests, he will excuse it as he “learned it to pick up chicks.” This excuse will actually get him the approval of his friends.

Why does John go through all this trouble to hide his passion? Because he’s afraid that that his friends will consider his interests in poetry as something that lessens his masculinity. He's afraid that women will think of him as weak for having a genuine interest developing his art. He's afraid of seeming as a man with no real interests in his financial future as art is dismissed as a flight of fancy.

We need to let men know that there is nothing wrong with wanting to better yourself with no endgame in mind. We need to let men know that there is no shame in having a passion and that wanting to be better doesn’t mean there is something wrong with you to begin with. We need to let men know that self-betterment isn’t something you do when your young and we actually need to teach our young men that they can always be better. Because the truth is, no matter how good you are, you can always be better.