9 Dating Lessons I Learned the Hard Way (so You Don’t Have to)

Dating sounds like a fun activity, but it’s frustratingly hard.

There are so many things that can go wrong and so many people who have no idea what they’re doing. You make mistakes that you don’t even know exist while ignoring red flags that could have been spotted miles away.

I was no different.

During my younger years, I had absolutely no filters. My judgments were wonky. I was clouded by my emotions. I chose all the wrong people and hurt myself repeatedly.

In a nutshell, my love life was hell.

Luckily, I learned and I grew. Over time, I became evidently better at drawing boundaries and assessing my romantic partners. I realised that dating could be fun and rewarding if you know how to do it right.

How? Here are 9 rules of thumb to keep in mind next time you’re out on a date.

1. Think like the rule, not the exception

“Rules” exist for a reason — it means something has happened many times to many people. And there’s a good chance it might happen to you too.

See, when I was younger, I didn’t get it. I kept doing the things that I knew would not end well — for example, getting attached too quickly to someone emotionally unavailable — and blindly thinking it would turn out differently for me.

It never did.

Thinking like the rule doesn’t mean individual differences don’t exist or anything falling out of the “rule” will go terribly wrong. It simply means preparing yourself for the most probable scenario. And whatever it is you end up doing, you’re informed and know your risks.

2. If you don’t feel like yourself, the relationship is wrong

Brianna Wiest wrote a brilliant article about determining the love of your life and I agreed with her 100% from my personal experiences and observations of happy people in my life.

“There is only one way to tell that someone is truly the love of your life, and it is this: they make you the best possible version of yourself that you can be.”

— Brianna Wiest.

A good relationship should enhance — not diminish — who you are. If you feel like you can’t be yourself around someone, they’re wrong for you.

3. If someone is interested in you, you will know. If you have to ask, they don’t

If someone’s words and actions aren’t consistent, they’re sending out mixed signals. Mixed signals are indeed very clear signals that someone isn’t sure about you.

If someone has strong feelings for you and has a serious intention with you, they will make it known to you one way or another.

If they indeed like you but don’t make it known to you or say one thing while doing another, ask yourself if you really want a partner who always leaves you confused — it’s your choice.

4. Believe what people say about themselves

If a date says negative things about themselves to you early on, they’re trying to manage your expectations.

Those negative things might be disguised as jokes, but they don’t come out of thin air — they come from a place called self-awareness or self-perception.

When a guy told me on the first date he was “married” to his job, I brushed it off and assumed that if we got closer he would make time for me. He didn’t. It became my fault for going along with him and getting attached.

My lesson learned is that if someone gives you any information about themselves, especially early on, pay attention — they know themselves better than you do.

5. If it’s not a yes, it’s a no

Many people make relationship decisions out of fear and a scarcity mindset.

They would rather be with anyone than be alone, so they cross the line between compromising and settling and end up in unfulfilling — or even miserable — relationships.

If this is you, you deserve better. And remember that, you might not be able to choose your parents but you can choose your romantic partner. So do it for yourself. If you can’t say a sure “yes” to someone, say no.

The same applies to consent.

6. Have expectations for your relationship, but don’t have expectations for the people you meet

There’s a big difference between having expectations for your relationship and for the people you meet.

Having expectations for your relationship is part of having standards and boundaries. It’s how you could ensure you’re treated well and your relationship serves your needs.

On the other hand, having expectations for the people you meet is forcing them to fill a role in your life while disregarding who they are as individuals. It doesn’t work.

That’s why you should keep your mind open with your new dates. You get to know them and assess them over time whether they’re the right partner for you. If they are not, they can jog on.

7. A relationship’s outcome is a matter of compatibility; inherent worth is irrelevant

When a relationship ends, people often blame themselves and internalise the idea that they’re unworthy of love. But it can’t be further from the truth.

Two people can be wonderful as individuals but horrible as a couple — it’s because you’re not compatible with each other and better off with other people.

Your worth is intact — the value you embody and can offer the world doesn’t disappear just because one person out of billions can’t appreciate it.

8. People don’t love you for the emotional energy you put into the relationship; they love you for who you are

When you date someone who’s a bit more distant and unattached than you are, it’s natural to feel anxious and put more of yourself into the relationship, hoping to make it work.

But remember that if someone doesn’t see you and appreciate you for who you are, no matter how much care and love you show them, it won’t make them act the same way towards you.

They love you and choose you because they decide so in their own time — just like you do other people. Don’t waste your energy and time on those who are incapable of treasuring you.

9. Respect is earned. Love is given — but only after respect has been earned

I used to think respect is given and love is earned, and it caused me to chase unavailable people and sell myself short, not knowing why I was mistreated.

Now I understand that the opposite works much better. It means 3 things:

  • Have strong boundaries — earn your own respect and teach people how to treat you.

  • Never fight for anyone’s interest or love — you’re already worthy of it, and loving someone is a choice.

  • Progress a relationship romantically only after you know there’s mutual respect — no healthy relationship can exist without respect.

Learning to set boundaries and build respect in relationships changed my life. I went from being anxiously single to happily committed, thanks to the trust and confidence I successfully instilled within myself in the process.

Looking back on the years I was single, dating definitely brought me way more anxiety and heartbreak than fun. It didn’t have to be that way if only I had learned to love myself and had more insight into how romantic relationships work, especially in the early days of dating.

These dating rules of thumb are the hard-earned lessons that I wish someone had taught me earlier. After I had gone to therapy and worked on my anxiety, I put myself out there again to look for a serious relationship, and these “rules” served me well. I hope they will help you too if that’s what you want.

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