The Lessons I Learned From Casual Dating


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For the majority of my life, I have been in serious and long term relationships. I never really explored the idea of casual dating because I believed that it wasn’t for me.

To an extent, that was true.

Until my long term girlfriend of 4 years left me. Rather than embrace the normal and healthy approach of recovery I practiced in the past, I lost touch of what was good for me.

Like most people who reach a certain stage in their adult life, I prioritized an easy way out rather than doing what was necessary. I jumped straight into dating as many people as I could in hopes of moving on after a breakup.

I suppose that plays a contributing factor in what I’m going to share below. But, the lessons do still hold merit.

I would be lying if I said that it wasn’t a thrilling, scary, confusing, enlightening, awkward, experimental and crazy experience of my life.

It’s genuinely fun to be dating someone new!

But there were two central questions that loomed over this entire period – is casually dating many people better than a serious relationship and is it without consequences?

I’m sure that answer will vary from person to person.

For me, however, it was finally time to answer that question. I spent years doing this.

And to be brutally honest, it wasn’t worth it.

The negatives outweigh the positives. The long term damage that occurred set me back years of my life.

The only saving grace from the entire experience was my ability to read someone’s character really quickly into a romantic encounter. So, I used that tool as a means of drawing up a list of all the traits I really want in a partner.

Thankfully, I was able to meet someone who ticks all those boxes and dare I say, I got lucky!

I’ve been in a serious relationship ever since but certain issues and demons from my dating stint actually affected me terribly during the early phases of my relationship.

Here’s some of the lessons I learned from casual dating. Take from it what you will and I hope you enjoy the read.

1. It’s never really casual

There were some people who didn’t care much for anything serious but the majority of dates often turned into more.

I’d find myself being questioned about the possibility of a relationship and when I didn’t respond in favor of it, I could sense a disappointing shift in the dynamic.

Casual dating seems to have an underlying expectation attached to it.

The possibility of finding love is not ruled off the table for most people.

This means that if you meet someone amazing and you have a great date or two, it’s difficult not to experience disappointment if they end the possibility of a serious relationship down the road.

The reverse is true too when you’re the one who wants something more and the person you’re casually dating doesn’t.

2. It’s expensive

Pretty self-explanatory but looking back, I spent thousands on dates over those years. I’m not saying it was a complete waste of time or anything but much of that money could have been invested in my life, family or business.

Half the time I would be on dates that I knew wouldn’t lead anywhere from the get-go.

But, I was bored and lonely so I figured it was a good idea. It wasn’t.

Casual dating can be expensive, especially if you’re having a string of first dates and you’re expected to pay.

3. You get really good at reading signs of attraction

This is actually one of the lessons or benefits of casual dating. Since you’re able to meet many different people and refine your approach, you begin to experiment and identify certain things that create certain reactions.

Honestly, I was terrible at reading signs of attraction but a few months into it, everything came naturally to me.

But, I would be amiss not to mention the horrendous miscalculations I made at first, especially when deciding when to make a move. But it made me better overall so that’s a win.

4. You meet some really great people and really terribly people

I have a love-hate relationship with this one because, on the one hand, I want to be grateful for all the wonderful people I met but on the other, I would like to forget some horrendous people.

It’s really not all sunshine and rainbows casually dating.

You can often find yourself across the table from someone who is rude, obnoxious, arrogant, uptight, boring or psycho.

And sometimes they leave you with a really tarnished view on romance and dating.

Washing those bad feelings and memories away takes some time.

The silver lining would be that you can really pick out good people from bad ones within a relatively quick time.

And when you do find the good ones, it’s like a breath of relief and the excitement overcomes you.

5. The thrill of the chase is addictive

I believe this to be the biggest problem I faced during my phase of casual dating.

For as long as I could remember, I thrived within a serious committed relationship.

But there was something about getting a person to want me that became addictive. So much so that it became the measuring stick for how long I spend with someone.

When things started to progress beyond that, I would check out and be ready to get someone else feeling this way.

It progressed to a point that I was unable to develop a deeper connection with anyone.

I’d sabotage any potential relationship because I knew what awaited me was another thrilling chase!

Now imagine being someone who starts developing feelings for a person who acts this way!

6. The sanctity of physical intimacy can be diminished

Eat your favorite meal every single day and it stops being your favorite, it’s just a meal.

That’s the problem with being physically intimate with too many people without any feelings attached to it.

That special feeling starts to disappear.

And that really affects the desire and enjoyment of being physically intimate in any form.

On the flip side, being intimate with someone you love is incomparable. There’s nothing like it.

7. Commitment becomes scary

A combination of the above-mentioned experiences creates this grander problem of commitment. First of all, you start to realize there’s a lot of people who can like you and who you can like.

Secondly, it becomes so easy to get them. So, you start to wonder why work so hard to get this one person.

Lastly, rather than deal with issues and investing so much time, energy and effort in one person, I could be meeting a bunch of people and having a fun time with no strings attached (so to speak).

These are toxic thoughts that can affect you even if it’s not how you are wired as a person.

Then there’s the fear of getting hurt or cheated on.

When you casually date, your heart isn’t attached to those people and you feel in total control of what happens or how you react in different situations.

Whereas a serious relationship requires some vulnerability to it. That can be scary to someone who has gotten used to casual dating.

8. Ghosting hurts you and other people

I’m not certain of how common this was back in the 80’s but ghosting is a real problem in this day and age.

One minute you’re hot and heavy and the next you’re unfriended and blocked.

No explanations. No closure. Just rejection.

And it hurts. What’s more painful is the negative effect it has on your character when you become the perpetrator of ghosting.

If you’ve been ghosted, then you know how much it hurts your self-esteem and feelings in general. Now imagine doing that to someone else.

It’s not all bad

Even though I sound really negative about casual dating, it can be fun and enjoyable if you do it at the right time and with the right intentions.

Being upfront and honest about your intentions could work in your favor.

It prevents anyone from getting the wrong idea and you can enjoy the experience without so much of the negative effects that come from dating without any rules.

There’s nothing wrong with dating to meet someone you like.

I mean, that’s inevitable and one of the few ways of meeting a special person. But if your ultimate objective is to just get person after person at any cost, then you’re treading into dangerous territory.

To answer those questions I mentioned earlier in this article, is casually dating many people better than a serious relationship and is it without consequences?

The answer is no to both of those questions.

With that being said, feel free to leave your thoughts in the comment section below and let’s discuss further the merits of casual dating.

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