7 Ways We Make Dating Harder Than it Should Be


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People hangout together at coffee shop

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, 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.

Nobody is honest about anything

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.

Too many people are 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 rule book, they’ll wonder why you changed so much when you finally reveal your true self down the road.

EVERYONE is jaded

I have spoken to thousands of men and women over the years since I’ve 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.

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 ourselves more harm than good. You’ll be surprised to find just how many people can relate to you.

We’re closer to our phones than with each other

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 anytime, 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, or 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.

We’ve stopped believing in love

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, cheating…that it’s almost become the norm. People are automatically skeptical of a happy relationship, and that will never bring them one themselves.

We’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 about 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.

We have no idea how the hell 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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  1. Mary Brown on February 7, 2018 at 4:15 pm

    Speak for yourself.If somebody would speak up and make a solid wise decision to call,text,take someone on a real date.I’m not selfish Mr.Mouth u are.You have to get past fear n speak up.Besides I have standards.Also I’m tired of paying for expensive dates and cheap dates that’s all about other preference. I’ve did it for to long.I want a true gentleman who not afraid to take me out ,text or call.go for walks,etc.It’s all about the heart with true actions.Good women n good men don’t remain single forever.They don’t wait 4 ever either on empty promise no action.Why don’t you step up to the plate and hit a home run?What’s the problem selfish?Chow now speak that language.Nobodys got time for this Bye

    • James Michael Sama on February 7, 2018 at 4:57 pm

      I’m sorry, but I have no idea what you’re talking about. You have left hundreds of comments on my articles and sent me countless emails, and not a single one has made any sense.

      Speak up? I have written over 800 articles on this website speaking up. I literally say these things on TALK SHOWS. I have seminars on the topic. I literally speak up on this for a living. What are you talking about?

      • Robert Collins on February 8, 2018 at 1:14 am

        Mary Brown is a fem bot program that is triggered on certain content. It is funny you haven’t figured it out.. Just wait until the #metoo feminazi bot starts accusing you of sexual harassment and rape be on your content.

      • James Michael Sama on February 8, 2018 at 8:33 am

        I’ve exchanged emails with this same person before and they even scheduled a call with me (which I declined)… didn’t think it was a bot (I get spam comments ALL the time) but this is much different.

        Totally possible I just didn’t realize it. Appreciate the feedback!

    • Amber on February 7, 2018 at 10:14 pm

      I don’t understand a single thing you are talking about in this reply Mary; content, syntax or grammar. Was your reply meant for someone else? Who is Mr. Mouth? I may regret asking this. This may be a dark, scary Rabbit Hole I’m about to crawl into. I have to say though, the affect and tone of your paragraph does make me think you have been treated awfully by someone in your past, or maybe present.

  2. multipleforks on February 7, 2018 at 4:38 pm

    AMEN! Great article! I have met so many jaded men, I have to tell so many women and men to just let their guard down and YES it’s like people have stopped believing in love, so I tell my friends I love them all the time. People need to stop it with the dating apps, they’re just horrible. Meet people the old fashioned way! Cheers!

    • lonstermash on February 7, 2018 at 4:49 pm

      Totally agree with you!!

    • James Michael Sama on February 7, 2018 at 5:01 pm

      It’s sad but true on both sides of the coin. Trying to help people understand that we still all want the same thing, we just need to open up about it.

  3. lonstermash on February 7, 2018 at 5:00 pm

    BRAVO!! For so many years, I have been saying almost word for word what you have been saying. At 47, I had to do a lot of my dating “the old fashioned way.” I had no dating apps/websites. I had to approach a woman IN PERSON, ask for her number, and then CALL her. I usually called within 24 hours, and it usually resulted in a date. I didn’t play games. I was genuine and sincere. Sometimes it led to a good relationship, and sometimes it didn’t. But when it did, the relationship was almost never tarnished with her being jaded by past men, and definitely never tarnished by me being jaded by past women, though each of us definitely had past experiences that weren’t exactly pleasant. And no one ever had a guard up. When the relationship ended, it ended due to us reaching an impasse as we learned more about each other, but that’s life. And even in this technology age, I still CALL women initially, rather than texting, and that was part of what really turned on my current girlfriend of the past 18 months. And we definitely have a “give and give” mentality, as have my other serious girlfriends.

  4. Amy on February 7, 2018 at 5:37 pm

    So true…

  5. Elizabeth on February 7, 2018 at 5:42 pm

    Spot on…. so many great points… Many of my clients (I’m a Life Coach/Relationship Coach/Author) who don’t know their worth. I share your blogs with many AND I would love to read your book (is this newly out?) Good luck with that and keep up the GREAT articles…. they’re high quality compared to the rest that I read (and I read a lot of them).

    • James Michael Sama on February 7, 2018 at 5:45 pm

      Thanks so much Elizabeth! That means a lot coming from a fellow coach and author. 🙂 I really appreciate you sharing the blogs, as well!

      The book came out in late September, I have a hyperlink in the article, but to save you the search: https://www.amazon.com/dp/0692959866

      Would love to hear what you think! (So far, the reviews are fantastic).

      Thanks again,

      – James

  6. Jenn on February 8, 2018 at 2:22 am

    I think one of the underlying themes related to the dating difficulties hinges on how as a culture, many of us live in poor relation to our own (individual) interior world. We often spend an inordinate amount of time, energy, and effort focused on the outward world–our image, posting the glitzy glam image on social media, our work, etc but then avoid the cultivation of the inward gaze. We can’t truly relate to another amazing individual on the planet if we can’t truly relate to ourselves. (and phones distract us from the interior world of ourselves) Many of us don’t know ourselves much at all. This is partly why we have no idea how to date and also why We spend too much time on the run from ourselves, our dreams, our passions, and thus shut down the core of our own unique, interior world–our thoughts, our feelings, our soul, the forces and ideas that drive us and make us the beautiful human beings that we are. I suspect we’ve become jaded precisely because there is an emptiness felt when we haven’t lived the life each individual soul is calling each of us to live. We tend to project our emptiness, our jadedness outward onto the exterior world, onto the people we date, and thus find many of them to be exactly the stuff we’re disgusted with in ourselves. I liked what you said recently about how everyone we date is good for the learning curve–in that we learn what we don’t want as well as what we do. I would add one bit more to that–sometimes the stuff we discover we don’t want in someone else is related to the unhealed wounds in us. We can use this to fuel the healing fountain and discover the forgotten parts of our own souls and thus help cultivate the healing of our own wounds.

  7. […] article was originally published at James Michael Sama. Reprinted with permission from the […]

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