10 Lessons We Can Learn from Old-School Dating


Please enter a valid email address.
Something went wrong. Please check your entries and try again.
Untitled design (24)


We seem to have lost sight of what it takes to build real, solid, healthy relationships. The past could provide some insight.

Not everything from generations past should make its way to the present (and thankfully, many things haven’t), but there are some aspects of relationship building that seem to be lacking in today’s dating culture:

1: Old-school dating put in the work.

Let’s face it — the concept of dating has been beaten into submission by ‘Netflix n’ Chill’ and ‘Hey, wanna hang out?’ texts. The idea of actually putting in time and effort to court a woman has completely gone by the wayside.

How many men put in the effort to make sure they walk on the street-side of the sidewalk? When was the last time a man pulled out your chair, or held your coat on a date? These basic acts of courtesy are disappointingly rare.

Men have no idea how to properly pursue women or make them feel valued, and women have no idea how to respond when a man does put in this type of effort. There are no set expectations because everyone is running around making things up as they go along.

The double-edged sword about this is that if women continue accepting a lower level of effort, then men will continue doing it. Why would they step up, if they’re getting what they want and trying less?

2: Old-school dating didn’t have an audience.

A relationship is between two people, not between two people and their 10,000 Instagram followers. Much like how wealthy people don’t need to tell you they’re wealthy, people who are in love don’t need to advertise it to everyone they know in order to prove it.

Old school love is perfectly happy feeling its own warmth. It is secure and confident in its own universe and it doesn’t need to prove itself to anyone. Sure, photos are a great way to create and reflect on memories together, but there is a difference between documenting your love, and trying to justify your love to an audience.

3: Old-school dating built a connection.

I don’t mean just physical connection — but emotional connection. Do you feel completely safe opening up to the person you’re dating? Have you told them about how your confidence suffers from being bullied as a child? Have you told them about how family gatherings are awkward because your aunt cheated on your uncle? How about the fact that they shouldn’t take it personal if you need to be alone for a day or two?

Do you feel safe being completely naked with them? I don’t mean literally naked — we all know that’s easy these days. I mean being mentally and emotionally naked. Completely exposed. This is what true intimacy is.

If we don’t take the time to make the person we’re with feel completely safe and secure with us, then we will never be able to form a deep, meaningful bond with the person who they truly are, at their very core — because we will never really see him or her. The best compliment you can give someone is that you feel safe with them. If you can’t sleep soundly beside someone at night, nothing else matters.

4: Old-school dating paid attention to detail.

Great relationships are not about give and take, they’re about give and give. Putting in effort for the person you love. The “I got this because it reminded me of you” effort. The “don’t worry, I’ll stay up and help you study” effort. The “I planned a weekend away so we can be alone” effort.

The type of effort that makes the person you’re dating feel like she’s the Amal to your George. Like he’s the Legend to your Teigen. The most important person in your life. Like you value, love, honor, and respect them.

But, why would you? Someone better might come along the next time you swipe right.

This type of mindset is what’s keeping us from fully committing to each other. That, paired with the ideology that things should be easy and just come our way. We shouldn’t have to put all that effort in, because we deserve for it to just…happen. We are nice, and kind, and friendly — so we deserve the reward of another person in our life, don’t we?

Being in a relationship is a privilege, not a right. And, it’s a privilege both people have to work to maintain.

5: Old-school dating gave a fresh start.

We have all been hurt in the past and made decisions we regret. The good news is, though, that every new relationship is a chance to start again with a person you’ve never met before. Each new man or woman is a new path in life with endless possibilities.

But then you start to think — you’ve been hurt, disappointed, lied to, cheated on. It’s just easier to assume that everyone is going to be the same, anyway.

Stop it. Stop it right now. If you approach a new relationship under the assumption that he is going to tell you he’s at home when he’s really out with his friends (like your ex did), or that she’s “just friends” with that guy she’s actually sleeping with (like your ex did) — you will automatically seek out and find flaws that reinforce your suspicions.

You will pick apart little tiny things they do, and say to yourself: “See! I knew he/she was just like the rest.”

Be honest with yourself: When you start dating someone new, are you really giving them a fair, honest chance to show you who they are? Or are you going into it with preconceived notions that you’ve fabricated in your mind? Not everyone lies, not everyone cheats, and not everyone will disappoint you. You just need to give them a chance.

7: Old-school dating didn’t have phones.

When was the last time you sat down without your phone and had a deep, meaningful conversation about your passions? Your dreams. Your aspirations. What drives you. I mean, are aliens real?!

When was the last time you felt that high school type of love? That youthful, genuine excitement that comes from actually connecting with a person? Do you even remember what it was like to fall asleep with someone else on the other end of the phone (that was probably attached to the wall?)

Our communication is like our attraction — on the surface. Perhaps you do this because you don’t want to disagree or find conflict with another person. I’d argue that finding conflicts can be a good thing. It allows you to work through an issue with someone, hear their viewpoint, and grow together.

Perhaps you avoid conflict because that’d just be too uncomfortable and take you out of your safe space. Or, perhaps you do it because you’ve just forgotten (or not learned) how to actually work together to reach a common conclusion. You shouldn’t have to argue if you can converse.

One thing is for sure: Effective communication is the backbone of any healthy relationship. Without your partner knowing your wants, needs, and desires; they’ll never be able to give them to you.

8: Old-school dating had men stepping up.

To the women — we know, you’re independent. You can do it yourself. You can pay your own bills. You can buy your own drinks. There is a time for a man to respect a woman’s independence, and a time for him to be a man and work to take care of her.

Men have to step up and do it, and women have to understand it doesn’t take away from her strength.

We have become so individualized that we need to constantly prove ourselves to other people, and we see being supported as a weakness. I’d argue that the real weakness is closing yourself off to allowing anyone to do anything for you — and — it hurts our relationships.

People who care about you want to contribute and add value to your life. They want to make you feel special, and important. And most of all, they want to feel this from you in return. A great relationship is two people who remain individual but also come together as one. You can have both.

9: Old-school dating looked beyond the filter.

Don’t get me wrong, I put Valencia or Hudson on my Instagram photos just as much as the next person, but the image-centric world we’re living in has taught us to believe that what’s on the surface is a priority.

How far from the truth that is.

Our society is so hung up on creating a life that looks good on the outside, that we’ve lost sight of what it means to create one that feels good on the inside. Let’s compare: Would you rather have someone who looks great in your selfies, or someone who will stand by your side and support you when a family member gets an illness?

Someone whose Tom Ford suit or Louboutins make them look red-carpet ready, or someone who will come home with your favorite food when you’ve had a rough day?
My grandmother always said: Don’t fall for someone’s hair, teeth, or money — because they can lose all of it. Their good heart will always remain.

10: Old-school dating fixed what was broken.

When you own a house, and a lightbulb goes out, what do you do? You fix the lightbulb, right? You don’t sell the entire house and walk away from it.

The same goes for relationships. These days, we are finding one small thing that’s wrong, and giving up the entire relationship. We are void of forgiveness — everyone makes mistakes and nobody is perfect (including you). Old school love gives another chance. It prioritizes the relationship.

People are losing sight of what it’s like to actually commit and work through issues together, as a team. No relationship is always sunshine and rainbows. There are challenges, failures, roadblocks, speedbumps. And, broken lightbulbs.

Of course, if something simply cannot be fixed, or if someone is abusive towards you in any way whatsoever, this is a completely different discussion and you should walk away immediately. I’m talking about challenges that can be overcome — if only we would try a little harder.

Let’s connect: Facebook | Twitter | Instagram | LinkedIn | Speaking & Consulting

Grab a copy of my best-selling book below:

Click here to get my book: Unlocking Love: 10 Keys to Finding The Love of Your Life (Even If It’s You).

This piece was originally published on JamesMSama.com.


  1. Sandra Willingham on January 2, 2021 at 6:14 pm

    I love this ..old school is what needs to be taught at home by example from both parents to their sons and daughters..as a mom with a son now 20 I have been teaching him how to treat a woman by treating me how I expect to be treated..with my daughters I taught them not to accept anything less ..married couples please do not stop courting each other show by example. These kids are growing up with no respect for themselves or others its a ME instant generation the changes need to start at home .early as possible..compassion respect consideration of others are old school ..teach your children well.

    • cafebedouin on January 2, 2021 at 8:11 pm

      On the other hand, the other side of chivalry is misogyny. Nothing wrong with what you or the OP and you are saying, but there’s also reasons the new generation is moving on because a lot of old school ideas were bad ones.

      • hmickeyjd on January 5, 2021 at 7:44 pm

        Yet no one ever says anything about the runaway misandry that’s out there now. Why?

      • cafebedouin on January 5, 2021 at 7:46 pm

        Because it’s a small problem comparatively.

    • Wilson on July 3, 2023 at 8:42 am

      How about non hetero, how can we (because I am gay man) get lesson from old school dating. Beside that I also agree about two comments above about misoginy and misandary in chivalry, and heck yeah either feminist or old-school people always see misandary as smaller problem (in fact that even can be bigger).

Leave a Reply

Website Stats

  • 39,223,351 Total Visitors


Download your free Ebook 15 Ways to Know You're Dating a Gentleman


This error message is only visible to WordPress admins

Error: No feed found.

Please go to the Instagram Feed settings page to create a feed.


Please enter a valid email address.
Something went wrong. Please check your entries and try again.
Untitled design (24)
%d bloggers like this: