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Having Trouble with Dating? Here’s Why No One Knows What They’re Doing Anymore

Here we are, in the 21st century. Gen-X’ers, Millenials, Gen-Whatever’ers are having a hard enough time as it is navigating massive student loan debts, high rents, and a difficult job market. To add the icing on the cake, they are floundering through the dating world slash hookup culture and quickly discovering that nobody knows what the hell they are doing.

That’s probably because there is no structure. There is no methodology. There is no progressive course of events. And many times, there are really no role models out there leading by example for what to even do.

Essentially, everyone is like a ship at sea without a destination. Maybe hoping to bump into another one every once in awhile and ask how to get to port, but everybody’s navigation seems to be broken.

I think a big part of this is the fact that people [particularly younger men and women] have completely lost sight of what ‘dating’ actually means. Then again, maybe they didn’t actually lose sight of it because they never knew in the first place. Many members of the more recent generations have grown up just ‘hanging out’ with each other and calling it a relationship.

Actually going to a movie (not that that’s the best date idea…) gave way to coming over to watch a movie – which was essentially just code words to make the invitation sound less forward. Calling a girl to actually ask her out on a date has become a last minute “Hey, want to hang out?” text that implies no effort or real meaning whatsoever.

A date is not a random, last minute invitation. When you are getting to know someone, a date should be planned. It doesn’t have to be extravagant or expensive, but it should actually bear some resemblance to a series of events that you put some conscious effort into in order to ensure both parties actually enjoy themselves.

But, this notion is on a quite obvious decline. I don’t think there is just one thing to blame. I think we are losing social skills despite “social media” that make people more uncomfortable around one another and perhaps contribute to less of a willingness to actually form a real life connection that doesn’t require a friend request.


I think we are losing the value of commitment. We see this in the job market, we see it with technology, and we are seeing it with significant others. Everything just seems to be a placeholder to keep us busy until something better comes along. And – this is happening with ‘relationships’ too. What happened to the honor of keeping your word? The dignity of standing by someone when things get difficult? The integrity of upholding the promises you made long after the mood that you made them in, has past?

It is all declining. And we are wondering why everyone is always complaining about the opposite sex.

Our young men are also getting flooded with mixed messages. Do women want to be equal, or do they want to be courted? Is there even a conflict between the two? Can’t chivalry and equality coexist? Should he still pay for dinner? These questions can be confusing to people who have not yet defined their own answers to believe in.

But…what if you get turned down? What if you get rejected? In a society where trophies are handed out just for participating, we are not learning to lose – therefore we are not learning to identify our weaknesses and improve them.

It is all declining. And it is taking the concept of dating and courtship down with it.


Men find themselves perpetually trapped in what they call the ‘friend zone’ and wonder why. Without asking a woman on a proper date, she has no reason to believe you even want to be anything more than friends. Hanging out or even going out for drinks or spending time in groups does not send her the message that you are serious about her.

If actually conveying to the woman you are interested in that you are interested in her isn’t a good reason to invite her on a real life date, I don’t know what is.

For this reason, think about how rare it is for a woman to be asked on a date. Women get approached constantly. They get complimented constantly. They get invited to clubs and parties and events and whatevers, constantly. But do you know what the difference is? Those men are not you. Those men are not putting in the effort to actually discover who she is. Those men are not taking the time to express interest in her and to do something together that would allow you to actually have a real conversation.

Let’s be honest – a lot of men out there are just trying to get into her pants. But you want more than that. Telling her isn’t enough, you’re going to have to show her.

I’m sure I am not the only one who has heard the low-hanging fruit analogy when it comes to dating. Men, in order to avoid rejection (and possibly effort), will do what is easiest. They will invite women to just hang out. They won’t approach the woman who they really want to get to know because she just might be out of his league. They will grab at the apple on the bottom branch, because hey, it’s easier.

And the whole time this is happening, the freshest fruits are in the top branches staying untouched because every man is thinking the same way. Little do they know, desirable women are probably not being asked on real dates as often as you might think.

Are you going to take the easy road and keep ‘hanging out,’ or are you going to take a chance and climb the tree? You might fall down a few times and get hurt, but you will become better on each climb to a new apple.

There are women out there waiting for someone to prove that all men are not the same. They are waiting for a man to take the initiative and invite them on a real, actual date. They are waiting for a man to climb the tree.

Is it going to be you?


More articles on James M. Sama’s Blog

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