7 Ways You Make Dating Way Harder Than It Should Be

It's time to get back to basics.

bored woman on date New Africa / Shutterstock

One of the things I could never explain to my late grandfather when he and I would talk about dating these days is why I couldn’t just go down to the country club or the local town dance to “meet girls.” Or, the Sons of Italy (think, Elks Lodge) where they’d have get-togethers and the parents would bring their adult kids who would soon become members themselves.

I just couldn’t make the point that these things no longer exist in the same context and that we’re now swiping, DM’ing, Match'ing, eHarmony’ing, and Bumbling our way right into confusion.


Most things get better with time. Equal rights, technology, medicine, and education. But…have dating and relationships really improved? Or were we better off during a simpler era? Here are seven ways we’re making this all more difficult than it needs to be.

Here are 7 ways you make dating way harder than it should be:

1. You're not honest about dating.

Why is it so difficult for people to say what they mean, and mean what they say? Literally one of the first things we are taught as children seems to go by the wayside the second we step into the dating scene. We “don’t want something serious” (but are secretly dying to find it), we “would really love to get to know you better” (until we have sex and I lose interest), we “just aren’t looking for a relationship right now” (until we meet someone who we’re more interested in).


Life (and dating) would be so much simpler if we actually knew what someone else was thinking. The truth may sting at first, but at least it doesn’t cause trust issues down the road.

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2. You're too worried about "the rules."

Do I have to wait 3 days to text them? How long should I hold eye contact before it seems creepy? What line should I use when sending a message on a dating app?

How about this: Just be genuine and authentic. The only way you’re going to attract someone who is going to love you for you is if they actually know who you are. If you’re always trying to follow some sort of rulebook, they’ll wonder why you changed so much when you finally reveal your true self down the road.


3. You're jaded.

I have spoken to thousands of men and women over the years since I started writing on this topic, and I don’t think I’ve had a single conversation where I didn’t hear about a traumatic past. I think, rather than being upset by this, we can see it as an opportunity.

An opportunity to understand that every person we encounter on a daily basis has been hurt, heartbroken, or just plain screwed over. Perhaps they have been abused, perhaps they’ve never even been in a relationship, and have always lived with rejection.

RELATED: The Loving Habit Only The Happiest Couples Have

The truth is that we never know what someone else has been through, but carrying our pasts with us as an excuse to remain disconnected from others who may help to heal us, is doing us more harm than good. You’ll be surprised to find just how many people can relate to you.


4. You're closer to your phone than other people.

Don’t get me wrong, I love social media, and none of you would be reading this today without it. But nothing is all good (or all bad), and one of the negatives of social media is that it has pulled us apart from each other. Ironically.

We may feel more connected since we can talk to anyone at any time, but the reality is that often times this is where it ends. People would rather have the new-age version of a pen pal where they text each other for months and never actually get together.

Or, they just don’t want to put in the effort to leave the house, or plan a date, put makeup on, or wear pants, so they settle for some Tinder swiping and sexting to round out the Friday night. Hey, it’s cheaper, too.

5. You've stopped believing in love.

As a result of being jaded, or seeing friends and family be hurt, many people have stopped believing that finding a happy relationship is even possible. If this is the mindset that we approach dating with, how can we ever expect to actually put in enough effort to make something work?


Think about it: If you started building a house but you were convinced that it was going to burn down before you even finished the walls, would you even start it in the first place? Of course not, there’d be no point.

That’s where we’re at now. We see so much divorce, betrayal, and cheating…that it’s almost become the norm. People are automatically skeptical of a happy relationship, and that will never bring them one themselves.

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6. You're too selfish to commit.

That’s right, I said it. You are selfish as hell. Hey, so am I. Being selfish isn’t always a bad thing. In fact, you need to be selfish in many ways in order to live a happy life. You need to take care of yourself, you need to do things that make you fulfilled, you need to eat right, exercise, and get enough rest.


The problem, though, arises when society has turned so far in on itself that it fails to recognize everyone else. WE want all of the likes. WE want all of the followers. WE want all of the attention. To compromise or to put someone else’s needs ahead of our own seems like a foreign language.

This reverts back to the point of being jaded because we automatically assume that giving a piece of ourselves to someone else will be taken advantage of. The truth is, when it’s the right person, they’ll be doing the same for you. Relationships aren’t about give-and-take, they’re about give-and-give.

7. You have no idea how to date in the first place.

Last, but most definitely not least, what is even considered a date these days anyway? We are so inundated with “Hey, wanna chill?” texts that we pretty much have to take what we can get in terms of invitations — or, do we?


As we begin to lower the bar for how we expect to be treated in a dating scenario, we begin to lower the bar for how we expect to be treated as that relationship progresses. The whole reason why I wrote my book in the first place was to help people develop their own self-worth to a point that they’d stop accepting sub-par treatment because if that’s the path you start out on with someone, it’s certainly not going to change over time.

We need to step up and put more effort into communication, courtship, and just bonding with other human beings in general. Unfortunately, this seems to be in a downward spiral.

However, I believe that we can change the shifting tides if we all choose to do our small parts and just put in a little more effort.

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James Michael Sama is an award-winning blogger on the topics of dating and relationships, having amassed over 30 million readers in just a year and a half. He writes and speaks on the topics of chivalry, romance, and happiness throughout the country and has been featured repeatedly in news segments, talk shows, and mainstream radio.